【结 构 式】 |
【分子编号】36417 【品名】1-(4-chlorophenyl)-2-[(2-[4-[2-(4-chlorophenyl)-2-oxoethoxy]phenyl]-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzoyl]-1-benzothiophen-6-yl)oxy]-1-ethanone 【CA登记号】 |
【 分 子 式 】C43H35Cl2NO6S 【 分 子 量 】764.72544 【元素组成】C 67.54% H 4.61% Cl 9.27% N 1.83% O 12.55% S 4.19% |
合成路线1
该中间体在本合成路线中的序号:(VIII)The cyclization of 3-methoxythiophenol (I) with 4-methoxyphenacyl bromide (II) by means of KOH in ethanol gives 2-(4-methoxyphenyl)-6-methoxybenzothiophene (III), which is treated with pyridinium hydrochloride at 220 C to yield 2-(4-hydroxyphenyl)-6-hydroxybenzothiophene (IV). The protection of the hydroxy groups of (IV) by reaction with 4-chlorophenacyl bromide (V) and K2CO3 - 18-crown 6 in refluxing ether affords the bis p-chlorophenacyloxy derivative (VI), which by a Friedel-Kraft's reaction with 4-(2-pyrrolidinoethoxy)benzoyl chloride (VII) by means of AlCl3 in refluxing dichloroethane is converted into 2-[4-(4-chlorophenacyloxy)phenyl]-3-[4-(2-pyrrolidinoethoxy)benzoyl]-6-(4-chlorophenacyloxy)benzothiophene (VIII). Finally, this compound is deprotected by treatment with Zn and acetic acid.
【1】 Jones, C.D.; Suarez, T.; 2-Phenyl-3-aroylbenzothiophenes useful as antifertility agents. DE 2647907; ES 452694; ES 452695; FR 2329271; GB 1570610; JP 52053851; US 4133814 . |
【2】 Jones, C.D.; Suarez, T.; 2-Phenyl-3-aroylbenzothiophenes useful as antifertility agents. DE 2647907; ES 452694; ES 452695; FR 2329271; GB 1570610; JP 52053851; US 4133814 . |
【3】 Blancafort, P.; Castañer, J.; Serradell, M.N.; LY-117018. Drugs Fut 1982, 7, 2, 112. |
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) | 25756 | 3-methoxybenzenethiol | 15570-12-4 | C7H8OS | 详情 | 详情 |
(II) | 21991 | 2-Methoxyphenacyl bromide; 2-bromo-1-(4-methoxyphenyl)-1-ethanone | 2632-13-5 | C9H9BrO2 | 详情 | 详情 |
(III) | 10121 | 4-(6-Methoxy-1-benzothiophen-2-yl)phenyl methyl ether; 6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophene | 63675-74-1 | C16H14O2S | 详情 | 详情 |
(IV) | 36414 | 2-(4-hydroxyphenyl)-1-benzothiophen-6-ol | C14H10O2S | 详情 | 详情 | |
(V) | 16720 | 2-bromo-1-(4-chlorophenyl)-1-ethanone; 2-Bromo-4'-chloroacetophenone | 536-38-9 | C8H6BrClO | 详情 | 详情 |
(VI) | 36415 | 1-(4-chlorophenyl)-2-(4-[6-[2-(4-chlorophenyl)-2-oxoethoxy]-1-benzothiophen-2-yl]phenoxy)-1-ethanone | C30H20Cl2O4S | 详情 | 详情 | |
(VII) | 36416 | 4-[2-(1-pyrrolidinyl)ethoxy]benzoyl chloride | C13H16ClNO2 | 详情 | 详情 | |
(VIII) | 36417 | 1-(4-chlorophenyl)-2-[(2-[4-[2-(4-chlorophenyl)-2-oxoethoxy]phenyl]-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzoyl]-1-benzothiophen-6-yl)oxy]-1-ethanone | C43H35Cl2NO6S | 详情 | 详情 |