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【结 构 式】 
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【分子编号】37099 【品名】2-[(E)-2-(4,5-dihydro-1H-imidazol-2-yl)-1-phenylethenyl]pyridine 【CA登记号】 |
【 分 子 式 】C16H15N3 【 分 子 量 】249.31532 【元素组成】C 77.08% H 6.06% N 16.85% |
合成路线1
该中间体在本合成路线中的序号：(VI)This compound can be obtained by two related ways: 1) The Wittig condensation of 2-benzoylpyridine (I) with diethyl cyanomethylphosphonate (II) by means of sodium ethoxide in hot ethanol gives 3-phenyl-3-(2-pyridyl)acrylonitrite (III), which is reduced with NaBH4 in refluxing ethanol to yield 3-phenyl-3-(2-pyridyl)propionitrite (IV). Finally, this compound is cyclized with ethylenediamine (V) at reflux temperature. 2) The cyctization of 3-phenyl-3-(2-pyridyl)acrylonitrite (III) with ethylenediamine (V) at reflux temperature gives 2-[2-phenyl-2-(2-pyridyl)viny]-2-imidazoline (VI), which is then reduced with H2 over Pd/C in ethanol.
| 【1】 Ishikawa, F.; Cyclic guanidines. X. Synthesis of 2-(2,2-disubstituted ethenyl- and ethyl)-2-imidazolines as potent hypoglycemics. Chem Pharm Bull 1980, 28, 5, 1394-1402. |
| 【2】 Castaner, J.; Hillier, K.; Blancafort, P.; Serradell, M.N.; DG-5128. Drugs Fut 1982, 7, 8, 550. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 32233 | 2-Benzoylpyridine; Phenyl(2-pyridinyl)methanone | 91-02-1 | C12H9NO | 详情 | 详情 |
| (II) | 10045 | Diethyl cyanomethylphosphonate | 2537-48-6 | C6H12NO3P | 详情 | 详情 |
| (III) | 37098 | (E)-3-phenyl-3-(2-pyridinyl)-2-propenenitrile | C14H10N2 | 详情 | 详情 | |
| (IV) | 37100 | 3-phenyl-3-(2-pyridinyl)propanenitrile | C14H12N2 | 详情 | 详情 | |
| (V) | 14754 | ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine；1,2-Ethanediamine | 107-15-3 | C2H8N2 | 详情 | 详情 |
| (VI) | 37099 | 2-[(E)-2-(4,5-dihydro-1H-imidazol-2-yl)-1-phenylethenyl]pyridine | C16H15N3 | 详情 | 详情 |