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苯甲醯乙腈(benzoylacetonitrile)烯 類衍生物作為起始物的新穎不對

稱有機合成

1 H-NMR、 13 C-NMR

光譜圖

10 9 8 7 6 5 4 3 2 1 ppm 1.48 2.21 5.26 0.97

0.82

1.00

4.75 1.81 1.80

Current Data Parameters NAME PCN-p-CN EXPNO 4 PROCNO 1 F2 - Acquisition Parameters Date_ 20120329 Time 13.45 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 2.2610421 sec RG 362 DW 69.000 usec DE 6.50 usec TE 298.3 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 - Processing parameters SI 16384 SF 400.1300087 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

10 9 8 7 6 5 4 3 2 1 ppm 1.14 1.36 1.15 5.22 1.02

0.95

1.00

1.93 3.11 2.00 1.87

Current Data Parameters NAME PCN-p-Br-1st EXPNO 4 PROCNO 1 F2 - Acquisition Parameters Date_ 20120327 Time 13.26 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 2.2610421 sec RG 181 DW 69.000 usec DE 6.50 usec TE 298.5 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 - Processing parameters SI 16384 SF 400.1300096 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

10 9 8 7 6 5 4 3 2 1 ppm 1.04 2.06 5.06 0.98

0.90

1.00

4.95 1.87

1.86

Current Data Parameters NAME PCN-p-NO2-1st EXPNO 5 PROCNO 1 F2 - Acquisition Parameters Date_ 20120327 Time 13.35 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 2.2610421 sec RG 256 DW 69.000 usec DE 6.50 usec TE 298.5 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 - Processing parameters SI 16384 SF 400.1300090 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

10 9 8 7 6 5 4 3 2 1 ppm 0.99 1.09 1.06 4.93 0.98

0.93

1.00

1.84 5.00 1.77

Current Data Parameters NAME PCN-p-Cl-1st EXPNO 5 PROCNO 1 F2 - Acquisition Parameters Date_ 20120327 Time 13.22 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 2.2610421 sec RG 256 DW 69.000 usec DE 6.50 usec TE 298.5 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 - Processing parameters SI 16384 SF 400.1300096 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 0 ppm

10 9 8 7 6 5 4 3 2 1 ppm 1.21 2.19 5.06 0.96

0.90

1.00

2.85 0.96 1.00 1.82 1.82

Current Data Parameters NAME PCN-m-NO2 EXPNO 3 PROCNO 1 F2 - Acquisition Parameters Date_ 20120328 Time 21.25 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 2.2610421 sec RG 256 DW 69.000 usec DE 6.50 usec TE 298.2 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 - Processing parameters SI 16384 SF 400.1300084 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

10 9 8 7 6 5 4 3 2 1 ppm 1.05 1.33 1.02 4.83 0.91

0.84

1.00

2.78 4.67 1.83

Current Data Parameters NAME PCN-Ph EXPNO 1 PROCNO 1 F2 - Acquisition Parameters Date_ 20120328 Time 11.03 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 2.2610421 sec RG 322.5 DW 69.000 usec DE 6.50 usec TE 298.3 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 - Processing parameters SI 16384 SF 400.1300096 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

10 9 8 7 6 5 4 3 2 1 ppm 1.37 2.28 1.24 6.92 1.07 3.09 0.83

1.00

3.97 3.07 1.85

Current Data Parameters NAME PCN-p-Me EXPNO 1 PROCNO 1 F2 - Acquisition Parameters Date_ 20120130 Time 11.45 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 2.2610421 sec RG 181 DW 69.000 usec DE 6.50 usec TE 299.3 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 - Processing parameters SI 16384 SF 400.1300109 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

10 9 8 7 6 5 4 3 2 1 ppm 2.48 1.13 6.03 1.05

0.87 1.00 2.92

1.96 1.87 3.03 1.84

Current Data Parameters NAME PCN-p-OMe EXPNO 1 PROCNO 1 F2 - Acquisition Parameters Date_ 20120120 Time 17.56 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 2.2610421 sec RG 128 DW 69.000 usec DE 6.50 usec TE 301.6 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 - Processing parameters SI 16384 SF 400.1300113 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 0 ppm

10 9 8 7 6 5 4 3 2 1 ppm 2.2 4

5.9 5

2.0 1

0.8 1

1.0 0

1.9 8

4.0 7

1.9 0

Current Data Parameters NAME Hui203 EXPNO 10 PROCNO 1 F2 - Acquisition Parameters Date_ 20110922 Time 9.40 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 2.2610421 sec RG 181 DW 69.000 usec DE 6.50 usec TE 299.7 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 - Processing parameters SI 16384 SF 400.1300096 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

10 9 8 7 6 5 4 3 2 1 ppm 2.51

6.57 1.10

0.99

1.00

2.10 1.01 3.32 2.07

Current Data Parameters NAME PCN-2-thienyl EXPNO 2 PROCNO 1 F2 - Acquisition Parameters Date_ 20120327 Time 13.30 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 2.2610421 sec RG 181 DW 69.000 usec DE 6.50 usec TE 298.4 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 - Processing parameters SI 16384 SF 400.1300096 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

10 9 8 7 6 5 4 3 2 1 ppm 1.13 1.20 1.18 5.57 1.08

0.96

1.00

6.44 0.98 5.46

Current Data Parameters NAME PCN-2-Nath EXPNO 2 PROCNO 1 F2 - Acquisition Parameters Date_ 20120327 Time 13.11 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 2.2610421 sec RG 128 DW 69.000 usec DE 6.50 usec TE 298.5 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 - Processing parameters SI 16384 SF 400.1300131 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

10 9 8 7 6 5 4 3 2 1 ppm 1.06 1.52 5.22 1.07 1.12

1.00

1.56 5.77 3.32

Current Data Parameters NAME PCN-o-Br EXPNO 6 PROCNO 1 F2 - Acquisition Parameters Date_ 20120217 Time 13.21 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 32768 SOLVENT DMSO NS 16 DS 0 SWH 7246.377 Hz FIDRES 0.221142 Hz AQ 2.2610421 sec RG 128 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 F2 - Processing parameters SI 16384 SF 400.1300018 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

10 9 8 7 6 5 4 3 2 1 ppm 0.99 1.10 1.08 5.01 0.99

0.90

1.00

1.85 1.84 1.88 1.81

Current Data Parameters NAME PCN-p-Br-p-Br EXPNO 1 PROCNO 1 F2 - Acquisition Parameters Date_ 20120327 Time 14.27 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 2.2610421 sec RG 322.5 DW 69.000 usec DE 6.50 usec TE 298.3 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 - Processing parameters SI 16384 SF 400.1300091 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 0 ppm

10 9 8 7 6 5 4 3 2 1 ppm 1.17 1.41 1.19 5.84 1.04

1.43 1.00 2.92

2.01 1.96 2.03 1.93

Current Data Parameters NAME Hui216 EXPNO 3 PROCNO 1 F2 - Acquisition Parameters Date_ 20111024 Time 20.52 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 32768 SOLVENT CDCl3 NS 8 DS 0 SWH 7246.377 Hz FIDRES 0.221142 Hz AQ 2.2610421 sec RG 71.8 DW 69.000 usec DE 6.50 usec TE 300.3 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 - Processing parameters SI 16384 SF 400.1300114 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

10 9 8 7 6 5 4 3 2 1 ppm 3.22 1.22 1.18 1.06

0.96 1.00

1.03

5.76 2.14 2.08

Current Data Parameters NAME H238 EXPNO 1 PROCNO 1 F2 - Acquisition Parameters Date_ 20111125 Time 21.03 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD 32768 SOLVENT CDCl3 NS 1 DS 0 SWH 9057.971 Hz FIDRES 0.276427 Hz AQ 1.8088436 sec RG 228.1 DW 55.200 usec DE 6.50 usec TE 296.9 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 14.00 usec PL1 0 dB SFO1 500.1330008 MHz F2 - Processing parameters SI 16384 SF 500.1300129 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

10 9 8 7 6 5 4 3 2 1 ppm 3.74 1.93

1.13

1.03

1.00

2.16 7.19 2.39

Current Data Parameters NAME Et-A-p-Br EXPNO 4 PROCNO 1 F2 - Acquisition Parameters Date_ 20120220 Time 11.36 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 32768 SOLVENT CDCl3 NS 1 DS 0 SWH 7246.377 Hz FIDRES 0.221142 Hz AQ 2.2610421 sec RG 71.8 DW 69.000 usec DE 6.50 usec TE 296.5 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 - Processing parameters SI 16384 SF 400.1300136 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

10 9 8 7 6 5 4 3 2 1 ppm 3.97 2.35

1.14

1.07

1.00

6.70 2.56 2.39

Current Data Parameters NAME Et-A-p-NO2 EXPNO 2 PROCNO 1 F2 - Acquisition Parameters Date_ 20120222 Time 11.43 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 2.2610421 sec RG 228.1 DW 69.000 usec DE 6.50 usec TE 299.1 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 - Processing parameters SI 16384 SF 400.1300078 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

10 9 8 7 6 5 4 3 2 1 ppm 3.08 1.24

0.41 1.02

1.00 0.38

0.35 0.99

14.65

Current Data Parameters NAME Me-A-p-Br-500 EXPNO 5 PROCNO 1 F2 - Acquisition Parameters Date_ 20120218 Time 17.01 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD 32768 SOLVENT Acetone NS 16 DS 0 SWH 9057.971 Hz FIDRES 0.276427 Hz AQ 1.8088436 sec RG 161.3 DW 55.200 usec DE 6.50 usec TE 300.0 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 14.00 usec PL1 0 dB SFO1 500.1330008 MHz F2 - Processing parameters SI 16384 SF 500.1297793 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

10 9 8 7 6 5 4 3 2 1 ppm 4.27

1.39

1.00 0.34

0.36 0.96

15.69

Current Data Parameters NAME Me-A-p-CN EXPNO 4 PROCNO 1 F2 - Acquisition Parameters Date_ 20120214 Time 22.10 INSTRUM spect PROBHD 5 mm BBO BB-1H PULPROG zg30 TD 32768 SOLVENT DMSO NS 16 DS 0 SWH 7246.377 Hz FIDRES 0.221142 Hz AQ 2.2610421 sec RG 256 DW 69.000 usec DE 6.50 usec TE 298.9 K D1 2.00000000 sec TD0 1 ======== CHANNEL f1 ======== NUC1 1H P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 - Processing parameters SI 16384 SF 400.1300017 MHz WDW EM SSB 0 LB 0 Hz GB 0 PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

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