Ph-CH=CH-CHO, 18), 368 (M+ + 2 – CO2Me + Me + Ph + Ph-CH=CH-CHO, 7), 366 (M+– CO2Me + Me + Ph + Ph-CH=CH-CHO, 21), 310 (M+ + 2 – Ph-CH=CH + 2 Ph-N-C=O, 8), 308 (M+– 2 Ph-N-C=O + Ph-CH=CH, 24), 229 (M+ – Ph-CH=CH + OCNPhCO + CO2Me + Cl-C6H4, 6), 131 [ Ph-CH=CH-C=O+, 100], 119 [ Ph-N-C=O+, 34], 103 [Ph-CH=CH+, 46], 91 [Ph-N+, 43], 77 [C6H5+, 54].
Second diastereomer (4e)II. IR (KBr, cm–1): νmax 3062 (Csp2–H), 2954 (Csp3–H), 1737 (C=O), 1705 (C=O,ester), 1570 (C=C,aromatic), 1496 (C=C,alken), 1226 (Csp2–O), 1075 (Csp3–O) cm–1.
1H NMR (400.13 MHz, DMSO): δ 3.50 (3H, s, OCH3), 3.79 (3H, s, OCH3), 5.70 (1H, dd, 3JHH = 16.0 Hz, 3JHH = 8.0 Hz, CH), 6.41 (1H, d, 3JHH = 8.0 Hz, CH), 6.90 (1H, d, 3JHH = 16.0 Hz, CH), 6.79, 7.17-7.57 (19H, m, CHaromatic).
13C NMR (100.6 MHz, CDCl3): δ 52.2 and 52.8 (2OCH3), 86.5 (CHNO), 88.0 (Cq), 99.6 (Cspiro), 120.5 (CH), 126.3 (2CH), 127.1 (2CH), 127.4 (CH), 128.0 (2CH), 128.4 (2CH), 128.5 (CH), 128.6 (CH), 128.7 (2CH), 129.0 (CH), 129.1 (4CH), 129.8 (CH), 131.5 (Cq), 133.4 (Cq), 134.5 (Cq), 134.9 (Cq), 138.6 (CH), 139.1 (Cq), 152.4 (Cq), 153.9, 162.6, 163.6 and 169.9 (4C=O).
MS: m/z (%):651 (M+ + 2, 1), 649 (M+, 1), 519 (M+ – Ph-CH=CH-CHO, 1), 517 (M+ – Ph-CH=CH-CHO, 3), 460 (M+ + 2 – Ph-CH=CH-CHO + CO2Me, 19), 458 (M+ – CO2Me + Ph-CH=CH-CHO, 57), 423 (M+ – Ph-CH=CH-CHO + Cl + CO2Me, 13), 368 (M+ + 2 – CO2Me + Me + Ph + Ph-CH=CH-CHO, 19),366 (M+– CO2Me + Me + Ph + Ph-CH=CH-CHO, 57), 305 (M+– Cl + Ph-CH=CH-C=O + Ph-N-C=O + CO2Me, 60), 244 (M+– Ph-CH=CH-C=O + 2 Ph-N-C=O + Cl, 16), 189 (M+– 3 Ph + 2 CO2Me + C6H4-Cl, 23), 161 (M+– 2 N-Ph + 2 CO2Me + Ph + C6H4-Cl, 26), 131 [ Ph-CH=CH-C=O+, 100], 119 [Ph-N-C=O+, 66], 103 [Ph-CH=CH+, 47], 77 [C6H5+, 45].
2-3-7- خواص فیزیکی و مشخصات طیفی دیمتیل-8-(3-متیلفنیل)-2،4-دیاکسو-1،3-دیفنیل-7-](E)-2-فنیلوینیل[-6-اکسا-1،3،8-تریآزا-اسپیرو[4.5]دک-9-ان-9،10-دیکربوکسیلات I](f4) و II(f4)[
از این واکنش دو دیاستریومر (4f)I و (4f)II با بازده برابر 48% از هر کدام بدست آمده است. دیاستریومر (4f)I دارای نقطه ذوب oC 169-167 و دیاستریومر (4f)II دارای نقطه ذوب oC 190-188 میباشد. مشخصات طیفی این ترکیب با استفاده از طیفهای H NMR1، C NMR13، IR و Mass که در صفحات130-125 فصل 3 آورده شده است به شرح زیر میباشند:
First diastereomer (4f)I .IR (KBr, cm–1): νmax 3061 (Csp2–H), 2952 (Csp3–H), 1740 (C=O), 1704 (C=O,ester), 1594 (C=C,aromatic), 1502 (C=C,alken), 1223 (Csp2–O), 1036 (Csp3–O) cm–1.
1H NMR (400.13 MHz, DMSO): δ 2.32 (3H, s, CH3), 3.58 (3H, s, OCH3), 3.85 (3H, s, OCH3), 5.02 (1H, d, 3JHH = 7.6 Hz, CH), 5.79 (1H, dd, 3JHH = 16.0 Hz, 3JHH = 7.6 Hz, CH), 6.47 (1H, d, 3JHH = 16.0 Hz, CH), 7.03-7.60 (19H, m, CHaromatic).
13C NMR (100.6 MHz, CDCl3): δ 21.1 (CH3), 52.4 and 52.9 (2OCH3), 87.1 (CHNO), 87.7 (Cq), 104.5 (Cspiro), 120.8 (CH), 126.3 (2CH), 127.1 (2CH), 128.2 (CH), 128.4 (2CH), 128.7 (2CH), 128.9 (CH), 129.0 (2CH), 129.1 (CH), 129.6 (2CH), 129.7 (2CH), 129.8 (2CH), 132.0 (Cq), 134.1 (Cq), 135.1 (Cq), 135.6 (Cq), 137.0 (CH), 138.5 (Cq), 151.2 (Cq), 154.0, 163.2, 164.9 and 168.8 (4C=O).
MS: m/z (%): 629 (M+, 1), 497 (M+ – Ph-CH=CH-CHO, 4), 438 (M+ – Ph-CH=CH-CHO + CO2Me, 39), 378 (M+ – Ph-CH=CH-CHO + Ph-N-C=O, 15), 363 (M+– Me + Ph-N-C=O + Ph-CH=CH-CHO, 16), 346 (M+– CO2Me + Me + Ph + Ph-CH=CH-CHO, 17), 286 (M+ – 2 Me + Ph-CH=CH + Ph-N-C=O + Ph-N, 45), 258 (M+– Ph-CH=CH + 2 Me + 2 Ph-N-C=O, 18), 131 [ Ph-CH=CH-C=O+, 92 ], 119 [ Ph-N-C=O+, 100], 91 [ Ph-N+, 34 ].
Second diastereomer (4f)II. IR (KBr, cm–1): νmax 3033 (Csp2–H), 2923 (Csp3–H), 1733 (C=O), 1706 (C=O,ester), 1579 (C=C,aromatic), 1502 (C=C,alken), 1225 (Csp2–O), 1072 (Csp3–O) cm–1.
1H NMR (400.13 MHz, DMSO): δ 2.31 (3H, s, CH3), 3.46 (3H, s, OCH3), 3.76 (3H, s, OCH3), 5.74 (1H, dd, 3JHH = 16.0 Hz, 3JHH = 8.0 Hz, CH), 6.43 (1H, d, 3JHH = 8.0 Hz, CH), 6.86 (1H, d, 3JHH = 16.0 Hz, CH), 6.73-7.57 (19H, m, CHaromatic).
13C NMR (100.6 MHz, CDCl3): δ 21.1 (CH3), 52.0 and 52.6 (2OCH3), 86.3(CHNO), 88.2 (Cq), 97.0 (Cspiro), 121.0 (CH), 126.3 (2CH), 127.1 (2CH), 127.7 (2CH), 128.1 (CH), 128.3 (CH), 128.6 (2CH), 128.8 (2CH), 128.9 (CH), 129.0 (2CH), 129.1 (2CH), 129.6 (2CH), 131.6 (Cq), 133.7 (Cq), 135.1 (Cq), 135.2 (Cq), 138.0 (CH), 138.5 (Cq), 153.3 (Cq), 153.9, 162.7, 163.8 and 170.2 (4C=O).
MS: m/z (%): 629 (M+, 1), 497 (M+ – Ph-CH=CH-CHO, 10), 438 (M+ – Ph-CH=CH-CHO + CO2Me, 82), 378 (M+ – Ph-CH=CH-CHO + Ph-N-C=O, 17), 363 (M+– Me + Ph-N-C=O + Ph-CH=CH-CHO, 30), 346 (M+– CO2Me + Me + Ph + Ph-CH=CH-CHO, 29), 286 (M+ – 2 Me + Ph-CH=CH + Ph-N-C=O + Ph-N, 67), 258 (M+– Ph-CH=CH + Me + Me + 2 Ph-N-C=O, 29), 131 [ Ph-CH=CH-C=O+, 100 ], 119 [ Ph-N-C=O+, 83], 103 [Ph-CH=CH+, 40], 91 [ Ph-N+, 37 ], 77 [C6H5+, 31], 51 [CH-N-C=C+, 9].
2-3-8- خواص فیزیکی و مشخصات طیفی دیمتیل-8-(2-برموفنیل)-2،4-دیاکسو-1،3-دیفنیل-7-](E)-2-فنیلوینیل[-6-اکسا-1،3،8-تریآزا-اسپیرو[4.5]دک-9-ان-9،10-دیکربوکسیلات I](g4) و II(g4)[
از این واکنش دو دیاستریومر (4g)I و (4g)II با بازده برابر 22% از هر کدام بدست آمده است. دیاستریومر (4g)I دارای نقطه ذوب oC 140-138 و دیاستریومر (4g)II دارای نقطه ذوب oC 189-187 میباشد. مشخصات طیفی این ترکیب با استفاده از طیفهای H NMR1، C NMR13، IR و Mass که در صفحات136-131 فصل 3 آورده شده است به شرح زیر میباشند:
First diastereomer (4g)I .IR (KBr, cm–1): νmax 3062 (Csp2–H), 2952 (Csp3–H), 1737 (C=O), 1708 (C=O,ester), 1595 (C=C,aromatic), 1497 (C=C,alken), 1218 (Csp2–O), 1040 (Csp3–O) cm–1.
1H NMR (400.13 MHz, DMSO): δ 3.55 (3H, s, OCH3), 3.84 (3H, s, OCH3), 5.15 (1H, d, 3JHH = 7.6 Hz, CH), 5.73 (1H, dd, 3JHH = 16.0 Hz, 3JHH = 7.6 Hz, CH), 6.57 (1H, d, 3JHH = 16.0 Hz, CH), 7.15-7.61 (19H, m, CHaromatic).
13C NMR (100.6 MHz, CDCl3): δ 52.4 and 52.9 (2OCH3), 85.4 (CHNO), 87.3 (Cq), 102.0 (Cspiro), 119.1(CH), 124.6 (Cq), 126.3 (2CH), 127.0 (2CH), 128.2 (CH), 128.3 (CH), 128.6 (2CH), 128.9 (CH), 129.1 (2CH), 129.2 (CH), 129.7 (2CH), 129.9 (2CH), 130.7 (CH), 131.9 (Cq), 132.2 (CH), 133.3 (CH), 134.2 (Cq), 135.0 (Cq), 137.4 (Cq), 137.9 (CH), 151.0 (Cq), 154.0, 162.5, 164.8 and 168.7 (4C=O).
MS: m/z (%): 695 (M+ + 2, 1), 693 (M+, 1), 563 (M+ + 2 – Ph-CH=CH-CHO, 9),561 (M+ – Ph-CH=CH-CHO, 9), 504 (M+ + 2 – Ph-CH=CH-CHO + CO2Me, 100), 502 (M+ – CO2Me + Ph-CH=CH-CHO, 100), 431 (M+ + 2 – Ph-CH=CH-CHO + CO2Me + Ph, 23), 429 (M+– Ph-CH=CH-CHO + CO2Me + Ph, 23), 352 (M+– Br + OCH3 + 3 Ph, 28), 325 (M++ 2 – Ph-CH=CH-CHO + 2 Ph-N-C=O, 19), 323 (M+– Ph-CH=CH-CHO + 2 Ph-N-C=O, 19), 281 (M+– 2 N-Ph + CO2Me + Me + Ph + Br, 19), 131 [Ph-CH=CH-C=O+, 85], 119 [ Ph-N-C=O+, 39], 103 [Ph-CH=CH+, 32], 77 [C6H5+, 20].
Second diastereomer (4g)II. IR (KBr, cm–1): νmax 3063 (Csp2–H), 2951 (Csp3–H), 1733 (C=O), 1704 (C=O,ester), 1594 (C=C,aromatic), 1497 (C=C,alken), 1270 (Csp2–O), 1031 (Csp3–O) cm–1.
1H NMR (400.13 MHz, DMSO): δ 3.43 (3H, s, OCH3), 3.76 (3H, s, OCH3), 5.73 (1H, dd, 3JHH = 16.0 Hz, 3JHH = 8.0 Hz, CH), 6.63 (1H, d, 3JHH = 8.0 Hz, CH), 7.01 (1H, d, 3JHH = 16.0 Hz, CH), 7.16-7.58 (19H, m, CHaromatic).
13C NMR (100.6 MHz, CDCl3): δ 52.1 and 52.6 (2OCH3), 85.0 (CHNO), 86.7 (Cq), 95.3 (Cspiro), 119.4 (CH), 124.9 (Cq), 126.3 (2CH), 126.9 (CH), 127.0 (2CH), 127.3 (CH), 127.5 (2CH), 127.9 (CH), 128.6 (2CH), 128.9 (CH), 129.0 (2CH), 129.1 (2CH), 129.2 (CH), 132.2 (CH), 132.5 (Cq), 133.5 (CH), 135.1 (Cq), 137.3 (Cq), 138.5 (CH), 139.3 (Cq), 152.5 (Cq), 153.9, 162.1, 163.5 and 169.9 (4C=O).
MS: m/z (%): 695 (M+ + 2, 1), 693 (M+, 1), 563 (M+ + 2 – Ph-CH=CH-CHO, 13), 561 (M+ – Ph-CH=CH-CHO, 13), 504 (M+ + 2 – Ph-CH=CH-CHO + CO2Me, 100), 502 (M+ – CO2Me + Ph-CH=CH-CHO, 100), 424 (M+– Br + CO2Me + Ph-CH=CH-C=O, 80), 352 (M+– Br + OCH3 + 3 Ph, 26), 325 (M++ 2 – Ph-CH=CH-CHO + Ph-N-C=O, 27), 323 (M+– Ph-CH=CH-CHO + Ph-N-C=O, 27), 281 (M+– 2 N-Ph + CO2Me + Me + Ph + Br, 22), 244 (M+– Br + Ph-CH=CH-CHO + 2 Ph-N-C=O, 75), 131 [Ph-CH=CH-C=O+, 43], 119 [ Ph-N-C=O+, 29], 103 [Ph-CH=CH+, 15], 77 [C6H5+, 10].
2-3-9- خواص فیزیکی و مشخصات طیفی دیمتیل-8-(2-متیلفنیل)-2،4-دیاکسو-1،3-دیفنیل-7-](E)-2-فنیلوینیل[-6-اکسا-1،3،8-تریآزا-اسپیرو[4.5]دک-9-ان-9،10-دیکربوکسیلات I](h4) و II(h4)[
از این واکنش دو دیاستریومر (4h)I و (4h)II با بازده برابر 30% از هر کدام بدست آمده است. دیاستریومر (4h)I دارای نقطه ذوب oC 176-174 و دیاستریومر (4h)II دارای نقطه ذوب oC 209-207 میباشد. مشخصات طیفی این ترکیب با استفاده از طیفهای H NMR1، C NMR13، IR و Mass که در صفحات142-137 فصل 3 آورده شده است به شرح زیر میباشند:
First diastereomer (4h)I .IR (KBr, cm–1): νmax 3062 (Csp2–H), 2920 (Csp3–H), 1737 (C=O), 1707 (C=O,ester), 1573 (C=C,aromatic), 1496 (C=C,alken), 1269 (Csp2–O), 1040 (Csp3–O) cm–1.
1H NMR (400.13 MHz, DMSO): δ 2.28 (3H, s, CH3), 3.59 (3H, s, OCH3), 3.85 (3H, s, OCH3), 5.05 (1H, d, 3JHH = 7.6 Hz, CH), 5.82 (1H, dd, 3JHH = 15.6 Hz, 3JHH = 7.6 Hz, CH), 6.48 (1H, d, 3JHH = 15.6 Hz, CH), 6.92 -7.60 (19H, m, CHaromatic).
13C NMR (100.6 MHz, CDCl3): δ 21.2 (CH3), 52.4 and 52.8 (2OCH3), 87.1 (CHNO), 87.6 (Cq), 104.8 (Cspiro), 121.0 (CH), 125.5 (CH), 126.4 (2CH), 127.0 (2CH), 128.2 (CH), 128.7 (2CH), 128.8 (CH), 128.92 (CH), 128.98 (CH), 129.0 (2CH), 129.1 (CH), 129.2 (CH), 129.7 (2CH), 129.8 (2CH), 131.9 (Cq), 134.1 (Cq), 135.2 (Cq), 136.8 (CH), 138.4 (Cq), 139.2 (Cq), 150.9 (Cq), 154.0, 163.1, 164.9 and 168.7 (4C=O).
MS: m/z (%): 629 (M+, 1), 497 (M+ – Ph-CH=CH-CHO, 7), 438 (M+ – Ph-CH=CH-CHO + CO2Me, 100), 363 (M+– Me + Ph-N-C=O + Ph-CH=CH-CHO, 48), 286 (M+– 2 Me + Ph-N + Ph-CH=CH + Ph-N-C=O, 28), 259 (M+ – Ph-CH=CH + 2 Ph-N-C=O + OMe, 16), 131 [

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