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【结 构 式】

【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information