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【结 构 式】 
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【分子编号】36144 【品名】(E)-3-(2-chloro-4-nitrophenyl)-2-propenal 【CA登记号】 |
【 分 子 式 】C9H6ClNO3 【 分 子 量 】211.60428 【元素组成】C 51.09% H 2.86% Cl 16.75% N 6.62% O 22.68% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of 2-chloro-4-fluorosulfonylbenzyl bromide (I) with triphenylphosphine (II) in refluxing benzene gives the corresponding triphenylphosphonium bromide (III), which is submitted to a Wittig condensation with 2-chloro-4-nitrocinnamaldehyde (IV) [prepared by an aldol condensation of 2-chloro-4-nitrobenzaldehyde (V) and acetaldehyde (VI)] yielding 1-(4-fluorosulfonyl-2-chlorophenyl)-4-(2-chloro-4-nitrophenyl)butadiene (VII). The reduction of (VII) with H2 over PtO2 in methoxyethanol affords 1-(4-fluorosulfonyl-2-chlorophenyl)-4-(2-chloro-4-aminophenyl)butane (VIII), which is finally cyclized with cyanoguanidine (IX) and acetone and treated with ethanesultonic acid.
| 【1】 Vermeulen, N.M.J.; Baker, B.R.; Irreversible enzyme inhibitors. CLXXVII. Active-site-directed irreversible inhibitos of dihydrofolate reductase derived from 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(phenylalkylphenyl)-s-triazines. J Med Chem 1970, 13, 6, 1154-60. |
| 【2】 Blancafort, P.; Serradell, M.N.; Castaner, J.; Hillier, K.; NSC-127,755. Drugs Fut 1983, 8, 7, 596. |
| 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) | 36142 | 4-(bromomethyl)-3-chlorobenzenesulfonyl fluoride | C7H5BrClFO2S | 详情 | 详情 | |
| (III) | 36143 | [2-chloro-4-(fluorosulfonyl)benzyl](triphenyl)phosphonium bromide | C25H20BrClFO2PS | 详情 | 详情 | |
| (IV) | 36144 | (E)-3-(2-chloro-4-nitrophenyl)-2-propenal | C9H6ClNO3 | 详情 | 详情 | |
| (V) | 36145 | 2-chloro-4-nitrobenzaldehyde | C7H4ClNO3 | 详情 | 详情 | |
| (VI) | 11974 | Acetaldehyde | 75-07-0 | C2H4O | 详情 | 详情 |
| (VII) | 36146 | 4-[(1E,3E)-4-(4-amino-2-chlorophenyl)-1,3-butadienyl]-3-chlorobenzenesulfonyl fluoride | C16H12Cl2FNO2S | 详情 | 详情 | |
| (VIII) | 36147 | 4-[4-(4-amino-2-chlorophenyl)butyl]-3-chlorobenzenesulfonyl fluoride | C16H16Cl2FNO2S | 详情 | 详情 | |
| (IX) | 23611 | N-cyanoguanidine | 461-58-5 | C2H4N4 | 详情 | 详情 |
| (X) | 29169 | 1-ethanesulfonic acid | 594-45-6 | C2H6O3S | 详情 | 详情 |