B. 磷兩性離子的應用
2. 實驗步驟及光譜數據
實驗步驟
(A) Preparation of 115aa : A dry and nitrogen-flushed 10-mL Schlenk flask, equipped with a magnetic stirring bar and a septum, was sequentially charged with a solution of 88a (81.1 mg, 0.5 mmol), 93a (83.1 mg, 1.1 equiv), Bu 3 P (150 μL, 1.2 equiv), PhCO 2 H (6.1 mg, 0.1 equiv), and pyrrolidine (4 μL, 0.1 equiv) in dry THF (0.5 mL). The reaction mixture was stirred for 1.5 h at room temperature (28-30
°C). Thereafter, the solvent was removed by evaporation in vacuo. Purification by flash-chromatography (ethyl acetate/hexanes: 1/3; then MeOH/CH 2 Cl 2 : 1/80) furnished 115aa as yellow solids (226.4 mg, 91% yield).
(B) Preparation of 119a : A dry and nitrogen-flushed 25-mL Schlenk tube, equipped with a magnetic stirring bar and a septum, was charged with a solution of 115aa (248.6 mg, 0.5 mmol), 118b (88 μL, 1.3 equiv), and Et 3 N (105 μL, 1.5 equiv) in dry toluene (5 mL). The reaction mixture was stirred for 1.5 h at room temperature (28-30 °C). Thereafter, the solvent was removed by evaporation in vacuo.
Purification by flash chromatography (CH 2 Cl 2 /hexanes: 2/3) furnished 119b as
實驗數據 in dry THF (0.5 mL) [reaction condition: 28-30 °C for 1.5 h]. Purification by
flash-chromatography (hexanes/ethyl acetate: 3/1 and then dichloromethane/methanol:
Synthesis of 115ab:
Prepared according to Typical Procedure (A) from
88a (81.1 mg, 0.5 mmol), 93b (83.1 mg, 1.1 equiv),
tributylphosphine (150.0 μL, 1.2 equiv), pyrrolidine
(4.1 μL, 0.1 equiv), and benzoic acid (6.1 mg, 0.1
equiv) in dry THF (0.5 mL) [reaction condition: 28-30 °C for 1.5 h]. Purification by
flash-chromatography (hexanes/ethyl acetate: 2/1 and then dichloromethane/methanol:
Synthesis of 115ac:
Synthesis of 115ad:
Prepared according to Typical Procedure (A) from 88a (81.1 mg, 0.5 mmol), 93d (75 μL, 1.1 equiv), tributylphosphine (150 μL, 1.2 equiv), pyrrolidine (4 μL, 0.1 equiv), and benzoic acid (6.1 mg, 0.1 equiv) in dry THF (0.5 mL) [reaction condition: 28-30 °C for 1.5 h]. Purification by
flash-chromatography (hexanes/ethyl acetate: 2/1 and then dichloromethane/methanol:
Synthesis of 115ae:
Prepared according to Typical Procedure (A) from 88a (81.1 mg, 0.5 mmol), 93e (72 mg, 1.1 equiv), tributylphosphine (150 μL, 1.2 equiv), pyrrolidine (4 μL, 0.1 equiv), and benzoic acid (6.1 mg, 0.1 equiv) in dry THF (0.5 mL) [reaction condition: 28-30 °C for 2 h]. Purification by
flash-chromatography (hexanes/ethyl acetate: 2/1 and then dichloromethane/methanol:
Synthesis of 115af:
Prepared according to Typical Procedure (A) from 88a (81.1 mg, 0.5 mmol), 93f (101.8 mg, 1.1 equiv), tributylphosphine (150 μL, 1.2 equiv), pyrrolidine (4 μL, 0.1 equiv), and benzoic acid (6.1 mg, 0.1 equiv) in dry THF (0.5 mL) [reaction condition: 28-30 °C for 0.5 h]. Purification by
flash-chromatography (hexanes/ethyl acetate: 2/1 and then dichloromethane/methanol:
Synthesis of 115ag:
Synthesis of 115ah:
Prepared according to Typical Procedure (A) from 88a (81.1 mg, 0.5 mmol), 93h (67 μL, 1.1 equiv), tributylphosphine (150 μL, 1.2 equiv), pyrrolidine (4 μL, 0.1 equiv), and benzoic acid (6.1 mg, 0.1 equiv) in dry THF (0.5 mL) [reaction condition: 28-30 °C for 0.5 h]. Purification by
flash-chromatography (hexanes/ethyl acetate: 2/1 and then dichloromethane/methanol:
Synthesis of 115ai:
Prepared according to Typical Procedure (A) from 88a (81.1 mg, 0.5 mmol), 93i (82.6 mg, 1.1 equiv), tributylphosphine (150 μL, 1.2 equiv), pyrrolidine (4 μL, 0.1 equiv), and benzoic acid (6.1 mg, 0.1 equiv) in dry THF (0.5 mL) [reaction condition: 28-30 °C for 0.5 h]. Purification by
flash-chromatography (hexanes/ethyl acetate: 2/1 and then dichloromethane/methanol:
Synthesis of 115aj:
Synthesis of 115ak:
Synthesis of 115al:
Synthesis of 115am:
Synthesis of 115an: 165.6, 153.8, 153.7, 130.3, 125.3, 124.3, 122.4, 122.3, 122.1, 121.7, 116.1, 91.5 (d, J
= 3.6 Hz), 91.2, 38.1 (d, J = 43.5 Hz), 35.3 (d, J = 42.3 Hz), 27.7, 27.2, 24.3 (d, J =
Synthesis of 115ao:
Synthesis of 115ap:
Prepared according to Typical Procedure (A) from 88a (81.1 mg, 0.5 mmol), 93p (73.9 mg, 1.1 equiv), tributylphosphine (150 μL, 1.2 equiv), pyrrolidine (4 μL, 0.1 equiv), and benzoic acid (6.1 mg, 0.1 equiv) in dry THF (0.5 mL) [reaction condition: 28-30 °C for 0.5 h]. Purification by
flash-chromatography (hexanes/ethyl acetate: 3/1 and then dichloromethane/methanol:
Synthesis of 115bb:
Prepared according to Typical Procedure (A) from 88b (56.1 mg, 0.5 mmol), 93b (83.1 mg, 1.1 equiv),
tributylphosphine (150 μL, 1.2 equiv), pyrrolidine (4 μL, 0.1 equiv), and benzoic acid (6.1 mg, 0.1 equiv) in dry THF (0.5 mL) [reaction condition: 28-30 °C for 0.5 h].
Purification by flash-chromatography (hexanes/ethyl acetate: 3/1 and then
dichloromethane/methanol: 100/1.2) yielded 115bb as yellow solid (217.1 mg, 97 %).
mp.: 163.7-164.1 °C; R f 0.38 (dichloromethane/methanol: 33/1)
1 H-NMR (400 MHz, CDCl 3 , 25 °C) δ/ppm: 8.12 (d, 2H, J = 8.6 Hz), 7.65 (d, 2H, J = 8.8, 1.9 Hz), 5.34 (d, 1H, J = 15.9 Hz), 2.40-2.20 (m, 7H), 2.11-1.96 (m, 3H), 1.88 (quint, 2H, J = 6.3 Hz), 1.48-1.25 (m, 12H), 0.91 (t, 9H, J = 7.0 Hz).
13 C-NMR (100 MHz, CDCl 3 , 25 °C) δ/ppm: 191.6 (d, J = 4.5 Hz), 147.1, 144.8, 130.8 (d, J = 4.9 Hz), 123.7, 107.4 (d, J = 2.7 Hz), 36.1 (d, J = 48.1 Hz), 36.0, 24.2 (d, J = 5.0 Hz), 23.9 (d, J = 15.0 Hz), 21.1, 21.0 (d, 1H, J = 47.4 Hz), 13.2.
31 P (200 MHz, CDCl 3 , 25 °C) δ/ppm: 32.9.
IR (KBr) ~ (cm −1 ): 2937 (m), 2863 (m), 1594 (w), 1491 (s), 1347 (m).
HRMS (ESI) for C 25 H 39 NO 4 P, [M+H] + (448.2617) found: 448.2602.
Synthesis of 115bg:
Synthesis of 115bm:
Synthesis of 115cg:
The compound 1cg is not very stable and slowly decomposes at room temperature.
mp.: 163.9-165.0 °C; R f 0.25 (hexanes/ethyl acetate: 1/2)
Synthesis of 115cm:
Synthesis of 115cp:
The compound 1cp is not very stable and slowly decomposes at room temperature.
mp.: 166.2-166.7 °C; R f 0.2 (hexanes/ethyl acetate: 1/2)
Synthesis of 115dg:
Synthesis of 115dm:
Synthesis of 115dp:
Synthesis of 1115eg:
Synthesis of 115fg:
Synthesis of 115fm:
Synthesis of 115gg 1 :
Prepared according to Typical Procedure (A) from 88g (73.1 mg, 0.5 mmol), 93g (56 μL, 1.1 equiv), tributylphosphine (150 μL, 1.2 equiv), pyrrolidine (4 μL, 0.1 equiv), and benzoic acid (6.1 mg, 0.1 equiv) in dry THF (0.5 mL) [reaction condition:
28-30 °C for 0.5 h]. Purification by flash-chromatography (hexanes/ethyl acetate: 3/1 and then dichloromethane/methanol: 100/2) yielded 115gg as white solid (209.1 mg, 96 %).
1 H-NMR (400 MHz, CDCl 3 , 25 °C) δ/ppm: 7.78-7.73 (m, 2H), 7.53 (d, 2H, J = 7.9 Hz), 7.38-7.28 (m, 3H), 4.90 (d, 1H, J = 16.7 Hz), 2.30-2.27 (m, 6H), 1.58-1.30 (m, 12H), 0.90 (t, 9H, J = 7.0 Hz).
13 C-NMR (100 MHz, CDCl 3 , 25 °C) δ/ppm: 183.1, 141.0, 135.1, 129.3 (d, J = 5.2
Hz), 129.0 (d, J = 5.0 Hz), 128.7, 128.3 (d, J = 2.7 Hz), 127.5, 65.5, 39.5 (d, J = 45.3
Hz), 24.1 (d, J = 5.2 Hz), 24.0 (d, J = 14.8 Hz), 20.1 (d, J = 45.7 Hz), 13.2.
Synthesis of 115gp:
The compound 115gp is not very stable and slowly decomposes at room temperature.
mp.: 96.7-97.2 °C; R f 0.2 (dichloromethane/methanol: 33/1)
Synthesis of 115hg:
The compound 115hg is not very stable and slowly decomposes at room temperature.
mp.: 122.6-123.3 °C; R f 0.31 (hexanes/ethyl acetate: 1/2)
Synthesis of 115hm:
The compound 115hm is not very stable and slowly decomposes at room temperature.
R f 0.38 (hexanes/ethyl acetate: 1/2)
Synthesis of 115aap:
Prepared according to Typical
Procedure (A) from 88a (162.1 mg, 1 mmol), 93p (67.1 mg, 0.5 equiv), tributylphosphine (300 μL, 1.2 equiv), pyrrolidine (4 μL, 0.1 equiv), and benzoic acid (6.1 mg, 0.1 equiv) in dry THF (0.5 mL) [reaction condition: 28-30 °C for 10 h]. Purification by flash-chromatography 7.8 Hz), 7.47-7.42 (m, 4H), 7.38-7.30 (m, 2H), 7.18-7.07 (m, 4H), 5.16 (pseudo-brs, 2H), 2.30-2.15 (m, 6H), 2.10-1.95 (m, 6H), 1.38-1.15 (m, 24H), 0.76 (t, 9H, J = 6.7 Hz), 0.70 (t, 9H, J = 6.9 Hz).
13 C-NMR (125 MHz, CDCl 3 , 25 °C) δ/ppm: 174.4, 165.8, 153.6, 153.9, 153.7, 130.5
130.4, 130.3, 130.2, 124.8, 122.4, 122.3, 122.2, 122.1, 116.1, 116.0, 94.1, 94.0, 36.8
(d, J = 40.5 Hz), 24.1 (d, J = 4.3 Hz), 24.0 (d, J = 4.2 Hz), 23.9 (d, J = 4.7 Hz), 23.7
Synthesis of 115ccp:
Prepared according to Typical Procedure (A) from 88c (146.1 mg, 1 mmol), 93p (67.1 mg, 0.5 equiv), tributylphosphine (300 μL, 1.2 equiv), pyrrolidine (4 μL, 0.1 equiv), and benzoic acid (6.1 mg, 0.1 equiv) in dry THF (0.5 mL) [reaction condition: 28-30 °C for 0.5 h]. Purification by flash-chromatography (dichloromethane/ethyl acetate: 2/1 and then dichloromethane/methanol: 100/3) yielded 115ccp as yellow solid (337.9 mg, 85 %).
The compound 115ccp is not very stable and slowly decomposes at room temperature.
R f 0.3 (dichloromethane/methanol: 33/1)
Synthesis of 115ddp:
Synthesis of 115aaq-1:
Prepared according to Typical Procedure (A) from 93q (67.1 mg, 0.5 mmol), 88a (162.1 mg, 2 equiv), tributylphosphine (300 μL, 2.4 equiv), pyrrolidine (4 μL, 0.1 equiv), and benzoic acid (6.1 mg, 0.1 equiv) in dry THF (0.5 mL) [reaction condition:
28-30 °C for 4 h]. Purification by flash-chromatography (hexane/ethyl acetate: 1/2
Synthesis of 115aaq-2:
The compound 115aaq-2 is not very stable and slowly decomposes at room temperature.
mp.: 90.0-91.0 °C; R f 0.35 (dichloromethane/methanol: 33/1)
1 H-NMR (400 MHz, CDCl 3 , 25 °C) δ/ppm: 8.04 (d, 2H, J = 7.5 Hz), 7.60-7.51 (m, 2H), 7.40 (d, 2H, J = 7.2 Hz), 7.25-7.15 (m, 5H), 5.13 (d, 2H, J = 15.8 Hz), 2.42-2.03 (m, 12H), 1.47-1.16 (m, 24H), 0.79 (t, 18H, J = 6.3 Hz).
13 C-NMR (100 MHz, CDCl 3 , 25 °C) δ/ppm: 174.3, 165.8 (d, J = 7.9 Hz), 153.9, 136.6, 131.0, 130.7, 130.0, 129.6, 125.1, 122.6, 122.3, 116.3, 94.4, 37.7 (d, J = 48.6 Hz), 24.4 (d, J = 5.1 Hz), 24.0 (d, J =15.1 Hz), 20.8 (d, J = 46.7 Hz), 13.3.
31 P (200 MHz, CDCl 3 , 25 °C) δ/ppm: 34.2.
IR (KBr) ~ (cm −1 ): 2966 (m), 2870 (m), 1649 (m), 1601 (s), 1539 (s), 1461 (s).
HRMS (ESI) for C 50 H 68 O 6 P 2 Na, [M+Na] + (849.4389) found: 849.4366.
Synthesis of 115dap:
Prepared according to Typical Procedure (A)
from 88a (81.1 mg, 0.5 mmol), 115dp (231.3
mg, 1 equiv), tributylphosphine (150 μL, 1.2
equiv), pyrrolidine (4 μL, 0.1 equiv), and
benzoic acid (6.1 mg, 0.1 equiv) in dry THF (0.5 mL) [reaction condition: 28-30 °C
for 7 h]. Purification by flash-chromatography (hexanes/ethyl acetate: 2/1 and then
Synthesis of 115cap:
Prepared according to Typical Procedure (A) from 88a (81.1 mg, 0.5 mmol), 115cp (232.3 mg, 1 equiv), tributylphosphine (150 μL, 1.2 equiv), pyrrolidine (4 μL, 0.1 equiv), and benzoic acid (6.1 mg, 0.1 equiv) in dry THF (0.5 mL) [reaction condition:
28-30 °C for 2 h]. Purification by flash-chromatography (hexanes/ethyl acetate: 2/1
Hz), 174.2, 165.9, 153.7, 153.6, 139.3, 139.2, 135.8, 135.7, 135.5, 130.6, 130.5, 130.4,
129.8, 124.9, 122.5, 122.2, 117.9, 117.8, 116.2, 116.1, 98.8, 98.2 (d, J = 2.5 Hz), 94.2,
Synthesis of 115cdp:
Prepared according to Typical Procedure (A) from 88c (73.1 mg, 0.5 mmol), 115dp (231.3 mg, 1 equiv), tributylphosphine (150 μL, 1.2 equiv), pyrrolidine (4 μL, 0.1 equiv), and benzoic acid (6.1 mg, 0.1 equiv) in dry THF (0.5 mL) [reaction condition: 28-30 °C for 0.5 h].
Purification by flash-chromatography (hexanes/ethyl acetate: 2/1 and then
Synthesis of 119a:
Prepared according to Typical Procedure (B) from 115aa (248.8 mg, 0.5 mmol), triethylamine (105 μL, 1.5 equiv), and 118a (76 μL, 1.3 equiv) in dry Toluene (5 mL) [reaction condition: 28-30 °C for 1 h].
Purification by flash-chromatography (hexanes/ethyl acetate: 8/1) yielded 119a as pale yellow solid (191.7 mg, 99 %).
mp.: 230.6-231.5 °C; R f 0.3 (hexanes/ethyl acetate: 8/1)
1 H-NMR (500 MHz, CDCl 3 , 25 °C) δ/ppm: 8.44-8.37 (m, 1H), 8.33-8.27 (m, 1H), 8.02 (dd, 1H, J = 8.0, 1.2 Hz), 7.88 (d, 1H, J = 7.7 Hz), 7.64 (t, 1H, J = 8.0 Hz), 7.58 (m, 1H), 7.54-7.51 (m, 3H), 7.45-7.33 (m, 4H).
13 C-NMR (125 MHz, CDCl 3 , 25 °C) δ/ppm: 157.4, 156.9, 152.7, 152.3, 148.3, 136.5, 132.0, 131.2, 129.6, 129.5, 128.9, 128.4, 126.9, 125.4, 124.7, 123.3, 121.0, 118.3, 117.3, 112.4, 110.8.
MS (70 eV, EI) m/z (%): 383 [M] + (100), 336 (65), 280 (20), 252 (40), 250 (30).
IR (KBr) ~ (cm −1 ): 3070 (w), 1741 (s), 1627 (w), 1524 (s), 1343 (m), 1093 (w).
HRMS (MALDI) for C 23 H 13 NO 5 Na, [M+Na] + (406.0692) found: 406.0701.
Synthesis of 119c:
Synthesis of 119g:
Prepared according to Typical Procedure (B) from 115aa (248.8 mg, 0.5 mmol), 118g (90 μL, 1.3 equiv), triethylamine (105 μL, 1.5 equiv), in dry Toluene (5 mL) [reaction condition: 28-30 °C for 1 h].
Purification by flash-chromatography (hexanes/dichloromethane: 3/1 and then dichloromethane) yielded 119g as white solid (184.5 mg, 88 %).
mp.: 150.3-150.9 °C; R f 0.28 (hexanes/dichlorormethane: 1/1)
1 H-NMR (400 MHz, CDCl 3 , 25 °C) δ/ppm: 8.40 (s, 1H), 8.36 (d, 1H, J = 8.2 Hz), 8.02 (d, 1H, J = 7.7 Hz), 7.86 (d, 1H, J = 7.6 Hz), 7.74-7.62 (m, 2H), 7.53-7.42 (m, 2H).
13 C-NMR (100 MHz, CDCl 3 , 25 °C) δ/ppm: 158.4, 156.3, 153.4, 148.0, 139.4 (q, 1H, J = 41.8 Hz), 135.9, 132.8, 129.3, 128.2, 125.7 (q, 1H, J = 1.7 Hz), 125.1, 125.0,
124.3, 121.7, 118.8 (q, 1H, J = 202.4 Hz), 117.5, 111.5, 109.4.
IR (KBr) ~ (cm −1 ): 2915 (w), 1753 (s), 1635 (w), 1531 (s), 1347 (s), 1122 (s).
HRMS (ESI) for C 18 H 8 F 3 NO 5 Na, [M+Na] + (398.0252) found: 398.0255.
Synthesis of 119h:
Prepared according to Typical Procedure (B) from 115ad (260.3 mg, 0.5 mmol), triethylamine (105 μL, 1.5 equiv), and 118h (142.6 mg, 1.3 equiv) in dry Toluene (5 mL) [reaction condition: 28-30 °C for 0.5 h]. Purification by flash-chromatography (hexanes/ethyl acetate: 10/1) yielded 119h as white solid (218.4 mg, 90%).
mp.: 188.4-188.9 °C; R f 0.3 (hexanes/ ethyl acetate: 10/1)
1 H-NMR (400 MHz, CDCl 3 , 25 °C) δ/ppm: 7.99 (d, 1H, J = 7.8 Hz), 7.71 (d, 2H, J = 8.4 Hz), 7.62 (d, 2H, J = 7.8 Hz), 7.57 (t, 1H, J = 7.5 Hz), 7.53-7.33 (m, 6H).
13 C-NMR (100 MHz, CDCl 3 , 25 °C) δ/ppm: 157.2, 157.0, 152.8, 150.9, 133.7, 132.1, 131.2, 130.7, 130.6 (q, J = 32.7 Hz), 128.3, 127.7, 125.6 (q, J = 3.7 Hz), 124.7, 124.0 (q, J = 272.1 Hz), 123.6, 121.0, 120.0, 117.4, 112.4, 110.9.
MS (20 eV, EI) m/z (%): 486 [M+2] + (94), 484 [M] + (100).
IR (KBr) ~ (cm −1 ): 3062 (w), 1749 (s), 1628 (w), 1480 (w), 1322 (s), 1163 (m), 1119 (m), 971 (w), 835 (w).
HRMS (MALDI) for C 24 H 12 BrF 3 O 3 Na, [M+Na] + (506.9820) found: 506.9833.
Synthesis of 119l:
Synthesis of 119s:
Prepared according to Typical Procedure (B) from 115gp (231.8 mg, 0.5 mmol), 118a (76 μL, 1.3 equiv),
triethylamine (105 μL, 1.5 equiv), in dry THF (2.5 mL) [reaction condition: 28-30 °C for 0.33 h]. Purification by flash-chromatography (hexanes/ethyl acetate: 23/1 and then dichloromethane/hexanes:
1/3) yielded 119s as ivory solid (148.5 mg, 85 %).
mp.: 168.0-169.2 °C; R f 0.25 (hexanes/dichloromethane: 1/1)
1 H-NMR (400 MHz, CDCl 3 , 25 °C) δ/ppm: 10.07 (s, 1H), 8.13-8.03 (m, 2H), 7.97 (d, 2H, J = 8.2 Hz),7.67 (d, 2H, J = 8.1 Hz), 7.56-7.45 (m, 5H), 7.37-7.32 (m, 3H).
13 C-NMR (100 MHz, CDCl 3 , 25 °C) δ/ppm: 191.5, 158.9, 149.4, 136.5, 136.1, 130.4, 130.3, 129.9, 129.2, 129.1, 128.8, 128.5, 127.6, 126.5, 125.5, 122.6, 114.3, 94.9.
IR (KBr) ~ (cm −1 ): 2723 (m), 2228 (m), 1697 (s), 1590 (m), 1480 (m), 1384 (s), 1203 (m).
HRMS (ESI) for C 24 H 15 NNaO 2 +
, [M+Na] + (372.1000) found: 372.0978.
Synthesis of 119t:
Prepared according to Typical Procedure (B) from 115gp (231.8 mg, 0.5 mmol), 118j (87 μL, 1.3 equiv), triethylamine (105 μL, 1.5 equiv), in dry THF (2.5 mL) [reaction condition: 28-30 °C for 0.17 h]. Purification by flash-chromatography (hexanes/dichloromethane: 3/1 and
then dichloromethane) yielded 119t as white solid (148.5 mg, 92 %).
mp.: 152.8-153.6 °C; R f 0.25 (hexanes/dichloromethane: 1/1)
1 H-NMR (500 MHz, CDCl 3 , 25 °C) δ/ppm: 10.08 (s, 1H), 8.01 (t, 4H, J = 8.5 Hz), 7.62 (d, 2H, J = 8.1 Hz),7.54-7.47 (t, 2H, J = 7.5 Hz), 7.47-7.42 (m, 1H), 2.82 (tt, 1H, J = 11.8, 3.0 Hz), 1.93-1.68 (m, 7H), 1.38-1.27 (m, 3H).
13 C-NMR (125 MHz, CDCl 3 , 25 °C) δ/ppm: 191.6, 158.4, 157.2, 136.6, 135.7, 130.2, 130.1, 129.4, 129.1, 128.1, 125.3, 121.0, 114.8, 92.6, 36.2, 31.7, 26.0, 25.7.
IR (KBr) ~ (cm −1 ): 2929 (s), 2856 (m), 2221 (w), 1701 (s), 1631 (m), 1564 (w), 1207 (w), 842 (m), 687 (m).
HRMS (ESI) for C 24 H 21 NO 2 Na, [M+Na] + (378.1470) found: 378.1476.
Synthesis of 119u:
Prepared according to Typical Procedure (B) from 115as (347.9 mg, 0.5 mmol), 118a (76 μL, 1.3 equiv), triethylamine (105 μL, 1.5 equiv), in dry Toluene (5 mL) [reaction condition: 28-30
°C for 1 h]. Purification by
flash-chromatography (hexanes/dichloromethane: 3/1 and then dichloromethane)
yielded 119u as ivory solid (264.2 mg, 90 %).
mp.: 221.9-222.9 °C; R f 0.25 (hexanes/dichloromethane: 1/1)
1 H-NMR (500 MHz, CDCl 3 , 25 °C) δ/ppm: 8.16-8.12 (m, 2H), 7.97-7.91 (m, 1H), 7.65-7.42 (m, 11H), 7.40-7.31 (m, 4H), 2.95 (tt, 1H, J = 11.6, 3.4 Hz), 1.99-1.73 (m, 7H), 1.46-1.32 (m, 3H).
13 C-NMR (100 MHz, CDCl 3 , 25 °C) δ/ppm: 159.9, 158.6, 157.9, 156.3, 152.4, 149.0, 130.7, 130.3, 130.2, 129.5, 129.1, 129.0, 128.9, 128.7, 128.1, 126.5, 125.5, 124.2, 123.6, 120.7, 118.4, 117.1, 114.8, 113.0, 109.6, 95.3, 36.1, 31.8, 26.1, 25.7.
IR (KBr) ~ (cm −1 ): 2929 (m), 2863 (m), 2221 (w), 1745 (s), 1631 (w), 1494 (w), 960 (m), 757 (m), 691 (m).
HRMS (ESI) for C 40 H 29 NO 4 Na, [M+Na] + (610.1994) found: 610.1964.
Synthesis of 119v:
Prepared according to Typical Procedure (B) from 115at (347.9 mg, 0.5 mmol), 118j (87 μL, 1.3 equiv), triethylamine (105 μL, 1.5 equiv), in dry Toluene (5 mL) [reaction condition: 28-30
°C for 1 h]. Purification by
flash-chromatography (hexanes/dichloromethane: 3/1 and then dichloromethane)
yielded 119v as light yellow solid (273.3 mg, 93 %).
mp.: 225.0-225.9 °C; R f 0.25 (hexanes/dichloromethane: 1/1)
1 H-NMR (500 MHz, CDCl 3 , 25 °C) δ/ppm: 8.05 (d, 2H, J = 7.8 Hz), 8.01 (d, 1H, J = 7.8 Hz), 7.65 (d, 2H, J = 8.1 Hz), 7.60-7.34 (m, 13H), 2.93 (tt, 1H, J = 11.8, 3.3 Hz), 1.96-1.70 (m, 7H), 1.43-1.28 (m, 3H).
13 C-NMR (125 MHz, CDCl 3 , 25 °C) δ/ppm: 158.0, 157.6, 156.7, 152.7, 151.9, 130.9, 130.8, 130.4, 129.8, 129.7, 129.1, 129.0, 128.9, 128.8, 128.7, 128.4, 127.0, 125.2, 124.5, 121.6, 120.9, 120.2, 117.2, 115.3, 112.7, 111.0, 93.0, 36.0, 31.8, 26.1, 25.7.
IR (KBr) ~ (cm −1 ): 2937 (w), 2228 (w), 1749 (m), 1631 (s), 960 (w), 694 (m).
HRMS (ESI) for C 40 H 29 NO 4 Na, [M+Na] + (610.1994) found: 610.2001.
Synthesis of 115as:
The compound 115as is not very stable and slowly decomposes at room temperature.
mp.: 162.4-163.0 °C; R f 0.35 (dichloromethane/ethyl acetate: 7/1)
1 H-NMR (500 MHz, CDCl 3 , 25 °C) δ/ppm: 8.08 (d, 3H, J = 7.5 Hz), 7.69 (d, 2H, J = 6.6 Hz), 7.55-7.40 (m, 8H), 7.34-7.20 (m, 5H), 5.51 (pseudo-brs, 1H), 2.41-2.21 (m, 6H), 1.50-1.30 (m, 12H), 0.89 (t, 9H, J = 6.1 Hz).
13 C-NMR (125 MHz, CDCl 3 , 25 °C) δ/ppm: 174.5, 166.1, 158.4, 153.8, 148.8, 136.0, 130.9, 130.4 (d, J = 4.7 Hz), 130.3 (d, J = 3.3 Hz), 130.2, 129.9, 129.8, 129.0, 128.8, 128.7, 127.9, 126.2, 125.4, 125.0, 123.0, 122.7, 122.0 116.3, 114.4, 95.4, 94.3, 37.2 (d, J = 47.4 Hz), 24.4 (d, J = 5.0 Hz), 23.9 (d, J = 14.9Hz), 20.5 (d, J = 46.4 Hz), 13.2.
31 P (200 MHz, CDCl 3 , 25 °C) δ/ppm: 34.6.
IR (KBr) ~ (cm −1 ): 2959 (m), 2870 (m), 2221 (w), 1653 (m), 1598 (s), 1539 (s), 1461 (s), 764 (m), 691 (m).
HRMS (ESI) for C 45 H 47 NO 4 P, [M+H] + (696.3243) found: 696.3219.
Synthesis of 115at:
The compound 115at is not very stable and slowly decomposes at room temperature.
mp.: 120.5-121.6 °C; R f 0.35 (dichloromethane/ethyl acetate: 7/1)
Synthesis of 119w:
Prepared according to Typical Procedure (B) from 115eg (347.9 mg, 0.5 mmol), 118h (142.6 mg, 1.3 equiv), triethylamine (105 μL, 1.5 equiv), in dry Toluene (5 mL) [reaction condition: 28-30 °C for 6 h]. Purification by flash-chromatography (hexanes/dichloromethane: 3/1)
yielded 119w as white solid (197.9 mg, 92 %).
mp.: 233.6-234.4 °C; R f 0.23 (hexanes/ethyl acetate: 10/1)
1 H-NMR (400 MHz, CDCl 3 , 25 °C) δ/ppm: 8.13 (d, 1H, J = 7.8 Hz), 7.62-7.55 (m, 1H), 7.53-7.40 (m, 1H), 7.35 (t, 1H, J = 7.5 Hz), 3.73 (s, 3H).
13 C-NMR (100 MHz, CDCl 3 , 25 °C) δ/ppm: 158.9, 154.0, 149.2, 138.3, 131.6, 131.1, 130.2, 129.7, 128.8, 128.4, 128.1, 127.7, 122.3, 122.2, 121.7, 121.2, 115.5, 114.9, 112.6, 29.0.
MS (20 eV, EI) m/z (%): 431 [M+2] + (100), 429 [M] + (95).
IR (KBr) ~ (cm −1 ): 3047 (m), 1653 (s), 1579 (s), 1100 (s), 665 (s).
HRMS (ESI) for C 24 H 16 BrNO 2 Na, [M+Na] + (452.0262) found: 452.0222.
Synthesis of 119x:
Prepared according to Typical Procedure (B) from 115eg (347.9 mg, 0.5 mmol), 118j (87 μL, 1.3 equiv), triethylamine (105 μL, 1.5 equiv), in dry Toluene (5 mL) [reaction condition: 28-30 °C for 6 h]. Purification by flash-chromatography (hexanes/dichloromethane: 3/2)
yielded 119x as white solid (197.9 mg, 95 %).
mp.: 222.9-223.4 °C; R f 0.15 (hexanes/dichloromethane: 1/1)
1 H-NMR (400 MHz, CDCl 3 , 25 °C) δ/ppm: 8.10-8.00 (m, 1H), 7.55-7.32 (m, 7H), 7.30 (t, 1H, J = 7.5 Hz), 3.72 (s, 3H) , 2.86 (tt, 1H, J = 11.7, 3.3 Hz), 1.95-1.70 (m, 7H), 1.41-1.27 (m, 3H).
13 C-NMR (100 MHz, CDCl 3 , 25 °C) δ/ppm: 159.4, 158.7, 153.6, 138.7, 131.4, 130.3 128.9, 127.8, 127.2, 121.9, 121.0, 119.0, 114.7, 114.1, 113.1, 35.9, 31.9, 29.1, 26.1, 25.8.
MS (20 eV, EI) m/z (%): 357 [M] + (100).
IR (KBr) ~ (cm −1 ): 3033 (m), 2922 (s), 2848 (s), 1653 (s), 1576 (s), 1104 (s).
HRMS (ESI) for C 24 H 24 NO 2 , [M+H] + (358.1807) found: 358.1785.
Synthesis of 119y:
Prepared according to Typical Procedure (B) from 115bb (223.8 mg, 0.5 mmol), 118a (76 μL, 1.3 equiv), triethylamine (105 μL, 1.5 equiv), in dry Toluene (5 mL) [reaction condition: 28-30 °C for 1 h]. Purification by flash-chromatography (hexanes/dichloromethane: 3/2)
yielded 119y as ivory solid (135.0 mg, 81 %).
mp.: 177.2-177.8 °C; R f 0.2 (hexanes/dichloromethane: 1/1)
1 H-NMR (400 MHz, CDCl 3 , 25 °C) δ/ppm: 8.21 (d, 2H, J = 8.8 Hz), 7.57 (d, 2H, J = 8.8 Hz), 7.37-7.27 (m, 5H), 3.03 (t, 2H, J = 6.3 Hz), 2.54 (t, 2H, J = 6.5 Hz), 2.26 (quint, 2H, J = 6.28 Hz).
13 C-NMR (100 MHz, CDCl 3 , 25 °C) δ/ppm: 193.9, 166.8, 150.1, 147.2, 139.2, 131.2, 129.1, 128.7, 126.6, 123.4, 120.7, 117.7, 38.5, 23.7, 22.3.
MS (20 eV, EI) m/z (%): 337 [M] + (100).
IR (KBr) ~ (cm −1 ): 3062 (m), 2929 (m), 1671 (s), 1594 (s), 1513 (s), 1343 (s), 1008 (s).
HRMS (ESI) for C 20 H 21 NO 4 Na, [M+Na] + (362.1368) found: 362.1343.
Synthesis of 119z:
Prepared according to Typical Procedure (B) from 115bb (223.8 mg, 0.5 mmol), 118j (87 μL, 1.3 equiv), triethylamine (105 μL, 1.5 equiv), in dry Toluene (5 mL) [reaction condition: 28-30 °C for 1 h]. Purification by flash-chromatography (hexanes/dichloromethane: 3/2)
yielded 119z as light yellow solid (184.5 mg, 92 %).
mp.: 147.9-149.0 °C; R f 0.2 (hexanes/dichloromethane: 1/1)
1 H-NMR (400 MHz, CDCl 3 , 25 °C) δ/ppm: 8.23 (d, 2H, J = 8.8 Hz), 7.50 (d, 2H, J = 8.8 Hz), 2.91 (t, 2H, J = 6.3 Hz), 2.63 (tt, 1H, J = 11.8, 3.3 Hz), 2.52-2.46 (m, 2H), 2.20 (quint, 2H, J = 6.4 Hz), 1.98-1.88 (m, 7H), 1.34-1.20 (m, 3H).
13 C-NMR (100 MHz, CDCl 3 , 25 °C) δ/ppm: 194.1, 166.2, 157.7, 146.8, 139.2, 130.6, 123.1, 119.2, 116.0, 38.4, 35.6, 31.7, 26.1, 25.6, 23.6, 23.4.
MS (20 eV, EI) m/z (%): 333 [M] + (40), 332 (100).
IR (KBr) ~ (cm −1 ): 3077 (m), 2922 (s), 2856 (s), 1668 (s), 1509 (s), 1336 (s), 1004 (s).
HRMS (ESI) for C 20 H 15 NO 4 Na, [M+Na] + (356.0899) found: 356.0871.
參考文獻
(3) Kumar, R.; Srinivasan, S.; Koduru, S.; Pahari, P.; Rohr, J.; Kyprianou, N.;
Damodaran, C. Cancer Prev. Res. 2009, 2, 234.
(4) Mitsunobu, O.; Yamada, M. Bull. Chem. Soc. Jpn. 1967, 40, 2380.
(5) Brunn, E.; Huisgen, R. Angew. Chem. Int. Ed. 1969, 8, 513.
(11) Gololobov, Y. G.; Kardanov, N. A.; Khroustalyov, V. N.; Petrovskii, P. V.
Tetrahedron Lett. 1997, 38, 7437.
(25) Nair, V.; Menon, R. S.; Vinod, A. U.; Viji, S. Tetrahedron Lett. 2002, 43,
(35) Singh, P.; Kumar, P.; Katyal, A.; Kalra, R.; Dass, S.; Prakash, S.; Chandra, R. Catal. Lett. 2010, 134, 303.
(36) Chhabra, B.; Bolte, M.; Crow, W. Aust. J. Chem. 1984, 37, 1795.
(37) Di Cosimo, J. I.; Díez, V. K.; Apesteguía, C. R. Applied Catalysis A:
General 1996, 137, 149.
(38) De Winter, M. L.; Nauta, W. T. Eur. J. Med. Chem. 1977, 12.
(39) Bernasconi, C. F.; Stronach, M. W. J. Am. Chem. Soc. 1991, 113, 2222.
(40) Zeidan, R. K.; Davis, M. E. J. Catal. 2007, 247, 379.
(47) Cadierno, V.; Gimeno, J.; Nebra, N. Adv. Synth. Catal. 2007, 349, 382.
(48) Cao, H.; Jiang, H.-F.; Huang, H.-W.; Zhao, J.-W. Org. Biomol. Chem.
2011, 9, 7313.
附錄一、
1 H-NMR& 13 C-NMR& 31 P-NMR 之光譜
9 8 7 6 5 4 3 2 1 ppm 9.02
11.99
2.92 3.37
1.00
1.95 0.97 1.02 1.92 1.03 0.95
NAME 180-3 EXPNO 8 PROCNO 1 Date_ 20110528 Time 17.07 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 16384 SOLVENT CDCl3 NS 1 DS 0 SWH 6009.615 Hz FIDRES 0.366798 Hz AQ 1.3632820 sec RG 40.3 DW 83.200 usec DE 6.50 usec TE 299.6 K D1 1.50000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1326008 MHz SI 16384 SF 400.1300079 MHz WDW EM SSB 0 LB 0.10 Hz GB 0 PC 1.00
160 140 120 100 80 60 40 20 ppm
-10 80 70 60 50 40 30 20 10 0 ppm
34.72
NAME Roy P EXPNO 20 PROCNO 1 Date_ 20110921 Time 18.01 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 100 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 295.7 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564921 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
8 7 6 5 4 3 2 1 ppm 9.21
12.10
2.96 3.05
1.00
1.98 1.00 1.88 1.01 1.94
NAME 170-4 EXPNO 2 PROCNO 1 Date_ 20110220 Time 16.04 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 16384 SOLVENT CDCl3 NS 1 DS 0 SWH 6009.615 Hz FIDRES 0.366798 Hz AQ 1.3632820 sec RG 50.8 DW 83.200 usec DE 6.50 usec TE 297.2 K D1 1.50000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec ======== CHANNEL f1 ======== NUC1 1H P1 11.20 usec PL1 0.00 dB SFO1 400.1326008 MHz SI 16384 SF 400.1300075 MHz WDW EM SSB 0 LB 0.10 Hz GB 0 PC 1.00
180 160 140 120 100 80 60 40 20 ppm
-10 70 60 50 40 30 20 10 0 ppm
34.49
NAME Roy P EXPNO 18 PROCNO 1 Date_ 20110921 Time 17.43 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 100 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 296.6 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564921 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
9 8 7 6 5 4 3 2 1 ppm 9.16
12.13
3.22 3.18
1.00
2.00 2.08 1.09 0.98 1.04 0.96
NAME 189 EXPNO 7 PROCNO 1 Date_ 20110529 Time 15.46 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 16384 SOLVENT CDCl3 NS 1 DS 0 SWH 6009.615 Hz FIDRES 0.366798 Hz AQ 1.3632820 sec RG 40.3 DW 83.200 usec DE 6.50 usec TE 300.0 K D1 1.50000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1326008 MHz SI 16384 SF 400.1300079 MHz WDW EM SSB 0 LB 0.10 Hz GB 0 PC 1.40
160 140 120 100 80 60 40 20 ppm
-10 80 70 60 50 40 30 20 10 0 ppm
36.90
NAME Roy P EXPNO 22 PROCNO 1 Date_ 20110921 Time 18.14 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 161 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 296.6 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564921 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
8 7 6 5 4 3 2 1 ppm 9.39
12.57
3.16 3.22
1.04
2.04 1.06 2.02 2.04 1.00
NAME 188 EXPNO 4 PROCNO 1 Date_ 20110227 Time 12.27 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 16384 SOLVENT CDCl3 NS 16 DS 0 SWH 6009.615 Hz FIDRES 0.366798 Hz AQ 1.3632820 sec RG 128 DW 83.200 usec DE 6.50 usec TE 303.8 K D1 1.50000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec ======== CHANNEL f1 ======== NUC1 1H P1 11.20 usec PL1 0.00 dB SFO1 400.1326008 MHz SI 16384 SF 400.1300086 MHz WDW EM SSB 0 LB 0.10 Hz GB 0 PC 1.00
180 160 140 120 100 80 60 40 20 ppm
-10 70 60 50 40 30 20 10 0 ppm
34.26
NAME Roy P EXPNO 44 PROCNO 1 Date_ 20110924 Time 14.33 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 100 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 295.9 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564860 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
9 8 7 6 5 4 3 2 1 ppm 9.30
12.37
3.15 3.11
1.03
2.07 1.05 2.03 2.04 1.00
NAME 176-4 EXPNO 6 PROCNO 1 Date_ 20110908 Time 16.45 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 32768 SOLVENT CDCl3 NS 16 DS 0 SWH 7246.377 Hz FIDRES 0.221142 Hz AQ 2.2611110 sec RG 90.5 DW 69.000 usec DE 6.50 usec TE 299.2 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz SI 16384 SF 400.1300003 MHz WDW EM SSB 0 LB 0.00 Hz GB 0 PC 1.00
160 140 120 100 80 60 40 20 ppm
-10 80 70 60 50 40 30 20 10 0 ppm
34.44
NAME Roy P EXPNO 30 PROCNO 1 Date_ 20110924 Time 11.36 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 77 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 296.2 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564860 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
8 7 6 5 4 3 2 1 ppm 9.10
12.54
3.00 3.20
0.97
2.06 5.18
1.00
NAME 169 EXPNO 3 PROCNO 1 Date_ 20110531 Time 11.57 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 16384 SOLVENT CDCl3 NS 1 DS 0 SWH 6009.615 Hz FIDRES 0.366798 Hz AQ 1.3632820 sec RG 57 DW 83.200 usec DE 6.50 usec TE 299.3 K D1 1.50000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1326008 MHz SI 16384 SF 400.1300082 MHz WDW EM SSB 0 LB 0.10 Hz GB 0 PC 1.40
180 160 140 120 100 80 60 40 20 ppm
-10 70 60 50 40 30 20 10 0 ppm
33.80
NAME Roy P EXPNO 36 PROCNO 1 Date_ 20110924 Time 12.03 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 82 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 296.0 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564860 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
9 8 7 6 5 4 3 2 1 ppm 9.18
12.43
6.08
0.92
5.19 1.10 2.01 1.00
NAME 173-4 EXPNO 6 PROCNO 1 Date_ 20110909 Time 10.26 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 32768 SOLVENT CDCl3 NS 16 DS 0 SWH 7246.377 Hz FIDRES 0.221142 Hz AQ 2.2611110 sec RG 71.8 DW 69.000 usec DE 6.50 usec TE 299.2 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz SI 16384 SF 400.1299990 MHz WDW EM SSB 0 LB 0.00 Hz GB 0 PC 1.00
160 140 120 100 80 60 40 20 ppm
-10 80 70 60 50 40 30 20 10 0 ppm
33.82
NAME Roy P EXPNO 34 PROCNO 1 Date_ 20110924 Time 11.54 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 79 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 296.1 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564860 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
8 7 6 5 4 3 2 1 ppm 9.21
12.23
6.00
3.08
0.95
2.00 2.07 1.05 1.95
1.00
NAME 174 EXPNO 1 PROCNO 1 Date_ 20101030 Time 13.22 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 16384 SOLVENT CDCl3 NS 16 DS 0 SWH 6009.615 Hz FIDRES 0.366798 Hz AQ 1.3632820 sec RG 35.9 DW 83.200 usec DE 6.50 usec TE 300.9 K D1 1.50000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec ======== CHANNEL f1 ======== NUC1 1H P1 11.20 usec PL1 0.00 dB SFO1 400.1326008 MHz SI 16384 SF 400.1300079 MHz WDW EM SSB 0 LB 0.10 Hz GB 0 PC 1.00
180 160 140 120 100 80 60 40 20 ppm
-10 70 60 50 40 30 20 10 0 ppm
33.54
NAME Roy P EXPNO 38 PROCNO 1 Date_ 20110924 Time 12.11 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 71 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 296.0 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564860 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
9 8 7 6 5 4 3 2 1 ppm 9.34
12.51
6.36
1.00
2.11
1.03 1.08 3.14 1.08
1.03
NAME 448-2 EXPNO 1 PROCNO 1 Date_ 20110509 Time 18.11 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 16384 SOLVENT CDCl3 NS 16 DS 0 SWH 6009.615 Hz FIDRES 0.366798 Hz AQ 1.3632820 sec RG 32 DW 83.200 usec DE 6.50 usec TE 299.2 K D1 1.50000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec ======== CHANNEL f1 ======== NUC1 1H P1 11.80 usec PL1 4.00 dB SFO1 400.1326008 MHz SI 16384 SF 400.1300086 MHz WDW EM SSB 0 LB 0.10 Hz GB 0 PC 1.40
160 140 120 100 80 60 40 20 ppm
-10 80 70 60 50 40 30 20 10 0 ppm
33.63
NAME Roy P EXPNO 40 PROCNO 1 Date_ 20110924 Time 14.15 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 78 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 295.8 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564860 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
8 7 6 5 4 3 2 1 ppm 9.40
12.30
6.00
0.94
1.94
2.06 0.78 0.97
0.97
NAME 192-2 EXPNO 6 PROCNO 1 Date_ 20110529 Time 16.38 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 16384 SOLVENT CDCl3 NS 1 DS 0 SWH 6009.615 Hz FIDRES 0.366798 Hz AQ 1.3632820 sec RG 32 DW 83.200 usec DE 6.50 usec TE 300.4 K D1 1.50000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1326008 MHz SI 16384 SF 400.1300082 MHz WDW EM SSB 0 LB 0.10 Hz GB 0 PC 1.40
180 160 140 120 100 80 60 40 20 ppm
-10 70 60 50 40 30 20 10 0 ppm
35.63
NAME Roy P EXPNO 28 PROCNO 1 Date_ 20110924 Time 11.28 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 50 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 11585.2 DW 6.200 usec DE 6.50 usec TE 295.8 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564860 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
9 8 7 6 5 4 3 2 1 ppm 9.24
12.07
6.14
0.89
0.98 3.87 1.04
1.00
NAME P spectra EXPNO 3 PROCNO 1 Date_ 20101118 Time 12.57 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 16384 SOLVENT CDCl3 NS 1 DS 0 SWH 6009.615 Hz FIDRES 0.366798 Hz AQ 1.3632820 sec RG 128 DW 83.200 usec DE 6.50 usec TE 301.2 K D1 1.50000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec ======== CHANNEL f1 ======== NUC1 1H P1 11.20 usec PL1 0.00 dB SFO1 400.1326008 MHz SI 16384 SF 400.1300083 MHz WDW EM SSB 0 LB 0.10 Hz GB 0 PC 1.40
160 140 120 100 80 60 40 20 ppm
-10 80 70 60 50 40 30 20 10 0 ppm
34.25
NAME P spectra EXPNO 4 PROCNO 1 Date_ 20101118 Time 12.59 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zgpg30 TD 131072 SOLVENT CDCl3 NS 42 DS 0 SWH 65359.477 Hz FIDRES 0.498653 Hz AQ 1.0027585 sec RG 14596.5 DW 7.650 usec DE 6.50 usec TE 301.3 K D1 1.50000000 sec d11 0.03000000 sec DELTA 1.39999998 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec ======== CHANNEL f1 ======== NUC1 31P P1 11.00 usec PL1 10.10 dB SFO1 161.9674741 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 0.00 dB PL12 16.50 dB PL13 19.50 dB SFO2 400.1318006 MHz SI 65536 SF 161.9757148 MHz WDW EM SSB 0 LB 2.00 Hz GB 0 PC 1.40
8 7 6 5 4 3 2 1 ppm 9.13 2.99 6.35 6.11
3.35 3.11
2.05
1.01
2.00 1.03
1.00
NAME 418-2 EXPNO 1 PROCNO 1 Date_ 20110517 Time 18.18 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 16384 SOLVENT CDCl3 NS 16 DS 0 SWH 6009.615 Hz FIDRES 0.366798 Hz AQ 1.3632820 sec RG 128 DW 83.200 usec DE 6.50 usec TE 300.1 K D1 1.50000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec ======== CHANNEL f1 ======== NUC1 1H P1 11.80 usec PL1 4.00 dB SFO1 400.1326008 MHz SI 16384 SF 400.1300086 MHz WDW EM SSB 0 LB 0.10 Hz GB 0 PC 1.00
180 160 140 120 100 80 60 40 20 ppm
-10 70 60 50 40 30 20 10 0 ppm
35.64
NAME Roy P EXPNO 46 PROCNO 1 Date_ 20110924 Time 14.47 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 45 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 296.1 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564860 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
9 8 7 6 5 4 3 2 1 ppm 3.18 9.29 18.09
8.34
0.45
0.49
2.08 1.02
1.00
NAME 197-2 EXPNO 18 PROCNO 1 Date_ 20111016 Time 23.04 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 32768 SOLVENT CDCl3 NS 26 DS 0 SWH 7246.377 Hz FIDRES 0.221142 Hz AQ 2.2611110 sec RG 114 DW 69.000 usec DE 6.50 usec TE 300.0 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz SI 16384 SF 400.1300016 MHz WDW EM SSB 0 LB 0.00 Hz GB 0 PC 1.00
160 140 120 100 80 60 40 20 ppm
-10 80 70 60 50 40 30 20 10 0 ppm
34.27
NAME Roy P EXPNO 14 PROCNO 1 Date_ 20110921 Time 17.03 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 50 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 296.1 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564921 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
8 7 6 5 4 3 2 1 ppm 9.40 3.22 3.17 12.69
6.51 1.02
0.53 0.51
2.10 1.03
0.52 0.48
NAME 194-2 EXPNO 6 PROCNO 1 Date_ 20101026 Time 17.18 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 16384 SOLVENT CDCl3 NS 16 DS 0 SWH 6009.615 Hz FIDRES 0.366798 Hz AQ 1.3632820 sec RG 45.3 DW 83.200 usec DE 6.50 usec TE 300.2 K D1 1.50000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec ======== CHANNEL f1 ======== NUC1 1H P1 11.20 usec PL1 0.00 dB SFO1 400.1326008 MHz SI 16384 SF 400.1300082 MHz WDW EM SSB 0 LB 0.10 Hz GB 0 PC 1.00
180 160 140 120 100 80 60 40 20 ppm
-10 70 60 50 40 30 20 10 0 ppm
34.30
NAME Roy P EXPNO 32 PROCNO 1 Date_ 20110924 Time 11.46 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 77 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 9195.2 DW 6.200 usec DE 6.50 usec TE 296.3 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564860 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
9 8 7 6 5 4 3 2 1 ppm 9.00
22.08
6.79
0.45
0.45
1.97 0.94
0.49 0.47
NAME Roy 195 EXPNO 1 PROCNO 1 Date_ 20110918 Time 16.06 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD 32768 SOLVENT CDCl3 NS 8 DS 0 SWH 9057.971 Hz FIDRES 0.276427 Hz AQ 1.8088988 sec RG 25.4 DW 55.200 usec DE 6.50 usec TE 295.2 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 14.00 usec PL1 0.00 dB SFO1 500.1330008 MHz SI 16384 SF 500.1299619 MHz WDW EM SSB 0 LB 0.00 Hz GB 0 PC 1.00
160 140 120 100 80 60 40 20 ppm
-10 80 70 60 50 40 30 20 10 0 ppm
34.12 34.14
NAME Roy P EXPNO 12 PROCNO 1 Date_ 20110921 Time 16.55 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 50 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 5792.6 DW 6.200 usec DE 6.50 usec TE 295.8 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564921 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
8 7 6 5 4 3 2 1 ppm 9.62
12.39
5.98
1.00
2.07 1.09 3.68 1.11
NAME 536 EXPNO 5 PROCNO 1 Date_ 20110724 Time 10.00 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 16384 SOLVENT CDCl3 NS 16 DS 0 SWH 6009.615 Hz FIDRES 0.366798 Hz AQ 1.3632820 sec RG 35.9 DW 83.200 usec DE 6.50 usec TE 299.5 K D1 1.50000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1326008 MHz SI 16384 SF 400.1300076 MHz WDW EM SSB 0 LB 0.10 Hz GB 0 PC 1.00
180 160 140 120 100 80 60 40 20 ppm
-10 70 60 50 40 30 20 10 0 ppm
34.26
NAME Roy P EXPNO 48 PROCNO 1 Date_ 20110924 Time 15.03 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 200 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 296.8 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564860 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
9 8 7 6 5 4 3 2 1 ppm 9.11
12.24 2.04 3.05 6.93
1.00
2.04
1.99
NAME 491 EXPNO 4 PROCNO 1 Date_ 20111016 Time 19.30 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 32768 SOLVENT CDCl3 NS 16 DS 0 SWH 7246.377 Hz FIDRES 0.221142 Hz AQ 2.2611110 sec RG 71.8 DW 69.000 usec DE 6.50 usec TE 299.9 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz SI 16384 SF 400.1299923 MHz WDW EM SSB 0 LB 0.00 Hz GB 0 PC 1.00
160 140 120 100 80 60 40 20 ppm
-10 80 70 60 50 40 30 20 10 0 ppm
32.91
NAME Roy P EXPNO 82 PROCNO 1 Date_ 20111017 Time 20.46 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 41 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 9195.2 DW 6.200 usec DE 6.50 usec TE 297.2 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564860 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
8 7 6 5 4 3 2 1 ppm 8.98
12.24
2.02 3.15 3.07 3.84
1.00
2.95 2.01
NAME 425-2 EXPNO 1 PROCNO 1 Date_ 20110507 Time 10.33 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 16384 SOLVENT CDCl3 NS 16 DS 0 SWH 6009.615 Hz FIDRES 0.366798 Hz AQ 1.3632820 sec RG 50.8 DW 83.200 usec DE 6.50 usec TE 298.8 K D1 1.50000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec ======== CHANNEL f1 ======== NUC1 1H P1 11.80 usec PL1 4.00 dB SFO1 400.1326008 MHz SI 16384 SF 400.1300086 MHz WDW EM SSB 0 LB 0.10 Hz GB 0 PC 1.00
180 160 140 120 100 80 60 40 20 ppm
-10 70 60 50 40 30 20 10 0 ppm
32.43
NAME Roy P EXPNO 42 PROCNO 1 Date_ 20110924 Time 14.24 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 108 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 295.8 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564860 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
9 8 7 6 5 4 3 2 1 ppm 3.13 9.48 18.35
11.52
1.00
NAME 493-2 EXPNO 8 PROCNO 1 Date_ 20111002 Time 15.22 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 32768 SOLVENT CDCl3 NS 32 DS 0 SWH 7246.377 Hz FIDRES 0.221142 Hz AQ 2.2611110 sec RG 35.9 DW 69.000 usec DE 6.50 usec TE 299.5 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz SI 16384 SF 400.1299725 MHz WDW EM SSB 0 LB 0.00 Hz GB 0 PC 1.00
160 140 120 100 80 60 40 20 ppm
-10 80 70 60 50 40 30 20 10 0 ppm
32.95
NAME Roy P EXPNO 6 PROCNO 1 Date_ 20110921 Time 16.35 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 50 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 295.7 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564921 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
8 7 6 5 4 3 2 1 ppm 9.00
12.13
6.03
1.00
7.11 2.01
NAME 426 EXPNO 7 PROCNO 1 Date_ 20110904 Time 21.20 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 16384 SOLVENT CDCl3 NS 16 DS 0 SWH 6009.615 Hz FIDRES 0.366798 Hz AQ 1.3632820 sec RG 35.9 DW 83.200 usec DE 6.50 usec TE 300.4 K D1 1.50000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1326008 MHz SI 16384 SF 400.1299924 MHz WDW EM SSB 0 LB 0.10 Hz GB 0 PC 1.40
180 160 140 120 100 80 60 40 20 ppm
-10 70 60 50 40 30 20 10 0 ppm
33.53
NAME Roy P EXPNO 68 PROCNO 1 Date_ 20111002 Time 22.21 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 50 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 295.8 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564860 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
9 8 7 6 5 4 3 2 1 ppm 3.16 9.44 18.67
5.81
1.00
2.22 1.90
NAME 495 EXPNO 4 PROCNO 1 Date_ 20110909 Time 21.11 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 32768 SOLVENT CDCl3 NS 16 DS 0 SWH 7246.377 Hz FIDRES 0.221142 Hz AQ 2.2611110 sec RG 71.8 DW 69.000 usec DE 6.50 usec TE 299.4 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz SI 16384 SF 400.1299985 MHz WDW EM SSB 0 LB 0.00 Hz GB 0 PC 1.00
160 140 120 100 80 60 40 20 ppm
-10 80 70 60 50 40 30 20 10 0 ppm
33.24
NAME Roy P EXPNO 70 PROCNO 1 Date_ 20111004 Time 19.20 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 42 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 9195.2 DW 6.200 usec DE 6.50 usec TE 295.8 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564860 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
8 7 6 5 4 3 2 1 ppm 9.08
12.36
6.01
0.98
4.13
4.02
NAME 539-2 EXPNO 2 PROCNO 1 Date_ 20110930 Time 8.05 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 32768 SOLVENT CDCl3 NS 16 DS 0 SWH 7246.377 Hz FIDRES 0.221142 Hz AQ 2.2611110 sec RG 35.9 DW 69.000 usec DE 6.50 usec TE 301.1 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz SI 16384 SF 400.1299849 MHz WDW EM SSB 0 LB 0.00 Hz GB 0 PC 1.00
180 160 140 120 100 80 60 40 20 ppm
-10 70 60 50 40 30 20 10 0 ppm
34.11
NAME Roy P EXPNO 60 PROCNO 1 Date_ 20110927 Time 18.07 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 42 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 8192 DW 6.200 usec DE 6.50 usec TE 296.4 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564860 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
9 8 7 6 5 4 3 2 1 ppm 9.03
12.21 6.11
5.53
0.90
3.00 1.85
NAME 459-2 EXPNO 5 PROCNO 1 Date_ 20110909 Time 16.31 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 32768 SOLVENT CDCl3 NS 16 DS 0 SWH 7246.377 Hz FIDRES 0.221142 Hz AQ 2.2611110 sec RG 40.3 DW 69.000 usec DE 6.50 usec TE 299.1 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 14.00 usec PL1 0.00 dB SFO1 400.1324008 MHz SI 16384 SF 400.1299963 MHz WDW EM SSB 0 LB 0.00 Hz GB 0 PC 1.00
160 140 120 100 80 60 40 20 ppm
-10 80 70 60 50 40 30 20 10 0 ppm
34.63
NAME Roy P EXPNO 8 PROCNO 1 Date_ 20110921 Time 16.41 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 50 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 8192 DW 6.200 usec DE 6.50 usec TE 295.6 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564921 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
8 7 6 5 4 3 2 1 ppm 3.01 9.05 17.48 5.89 6.04
1.00
NAME Roy 499 EXPNO 1 PROCNO 1 Date_ 20110921 Time 13.55 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD 32768 SOLVENT CDCl3 NS 4 DS 0 SWH 9057.971 Hz FIDRES 0.276427 Hz AQ 1.8088988 sec RG 71.8 DW 55.200 usec DE 6.50 usec TE 295.5 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 14.00 usec PL1 0.00 dB SFO1 500.1330008 MHz SI 16384 SF 500.1300131 MHz WDW EM SSB 0 LB 0.00 Hz GB 0 PC 1.00
180 160 140 120 100 80 60 40 20 ppm
-10 70 60 50 40 30 20 10 0 ppm
34.54
NAME Roy P EXPNO 4 PROCNO 1 Date_ 20110921 Time 16.18 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 50 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 296.1 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564921 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
9 8 7 6 5 4 3 2 1 ppm 9.22
12.29 5.94 3.47 3.10
1.01
2.03 2.01
NAME Roy P EXPNO 49 PROCNO 1 Date_ 20110925 Time 13.12 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD 32768 SOLVENT CDCl3 NS 4 DS 0 SWH 9057.971 Hz FIDRES 0.276427 Hz AQ 1.8088988 sec RG 90.5 DW 55.200 usec DE 6.50 usec TE 295.5 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 14.00 usec PL1 0.00 dB SFO1 500.1330008 MHz SI 16384 SF 500.1300126 MHz WDW EM SSB 0 LB 0.00 Hz GB 0 PC 1.00
160 140 120 100 80 60 40 20 ppm
-10 80 70 60 50 40 30 20 10 0 ppm
35.13
NAME Roy P EXPNO 50 PROCNO 1 Date_ 20110925 Time 13.15 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 103 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 296.2 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564860 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00
8 7 6 5 4 3 2 1 ppm 9.24
12.43
6.34
3.12
0.95
4.83 1.07 2.08
1.00
NAME 427 EXPNO 3 PROCNO 1 Date_ 20110503 Time 18.25 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 16384 SOLVENT CDCl3 NS 16 DS 0 SWH 6009.615 Hz FIDRES 0.366798 Hz AQ 1.3632820 sec RG 50.8 DW 83.200 usec DE 6.50 usec TE 298.9 K D1 1.50000000 sec MCREST 0.00000000 sec MCWRK 0.01500000 sec ======== CHANNEL f1 ======== NUC1 1H P1 11.80 usec PL1 4.00 dB SFO1 400.1326008 MHz SI 16384 SF 400.1300082 MHz WDW EM SSB 0 LB 0.10 Hz GB 0 PC 1.00
180 160 140 120 100 80 60 40 20 ppm
-10 70 60 50 40 30 20 10 0 ppm
32.89
NAME Roy P EXPNO 10 PROCNO 1 Date_ 20110921 Time 17.12 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD 65536 SOLVENT CDCl3 NS 50 DS 0 SWH 80645.164 Hz FIDRES 1.230548 Hz AQ 0.4063794 sec RG 20642.5 DW 6.200 usec DE 6.50 usec TE 296.1 K D1 2.00000000 sec D11 0.03000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 31P P1 12.00 usec PL1 6.00 dB SFO1 202.4462122 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 90.00 usec PL2 -0.60 dB PL12 15.00 dB PL13 18.00 dB SFO2 500.1320005 MHz SI 32768 SF 202.4564921 MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC 1.00