• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】27955

【品名】1-(4-[2-[(4-chlorophenyl)sulfanyl]ethoxy]-3-iodo-5-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione

【CA登记号】

【 分 子 式 】C28H28ClIO7S

【 分 子 量 】670.94929

【元素组成】C 50.12% H 4.21% Cl 5.28% I 18.91% O 16.69% S 4.78%

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:(XIX)

In a related procedure, iodination of acetophenone (XI) gave (XII). Subsequent alkylation of (XII) with dibromoethane afforded bromoethyl ether (XIII), which was converted to sulfide (XIV) by condensation with 4-chlorothiophenol (IX). Mannich reaction of (XIV) with paraformaldehyde and dimethylamine hydrochloride produced tertiary amine (XV), which was quaternized to (XVI) with MeI. Elimination in the resulting ammonium salt (XVI) produced vinyl ketone (XVII). Diketone (XIX) was then obtained by condensation with trimethoxybenzaldehyde (XVIII) in the presence of thiazolium salt (IV). Reduction of both ketone groups of (XIX) using NaBH4 yielded diol (XX), which was further cyclized with orthophosphoric acid in refluxing benzene to furnish a diastereomeric mixture of cis and trans diaryltetrahydrofurans (XXI). Iodine displacement in (XXI) with CuCN produced the corresponding diastereomeric mixture of cyanides, from which the target trans isomer was isolated by column chromatography.

1 Ram, B.; et al.; (±)-Trans-2-[3-methoxy-4-(4-chlorophenyl thioethoxy)-5-cyanophenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran, a potent PAF-receptor antagonist. Tetrahedron 1999, 55, 33, 10163.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10252 1,2-Dibromoethane; Ethylene dibromide 106-93-4 C2H4Br2 详情 详情
(IV) 27942 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride 4568-71-2 C13H16ClNOS 详情 详情
(IX) 27947 4-chlorobenzenethiol 106-54-7 C6H5ClS 详情 详情
(XI) 22604 1-(4-hydroxy-3-methoxyphenyl)-1-ethanone;Acetovanillone;4’-hydroxy-3’-methoxyacetophenone;1-(4-hydroxy-3-methoxyphenyl)ethanone 498-02-2 C9H10O3 详情 详情
(XII) 27949 1-(4-hydroxy-3-iodo-5-methoxyphenyl)-1-ethanone C9H9IO3 详情 详情
(XIII) 27950 1-[4-(2-bromoethoxy)-3-iodo-5-methoxyphenyl]-1-ethanone C11H12BrIO3 详情 详情
(XIV) 27951 1-(4-[2-[(4-chlorophenyl)sulfanyl]ethoxy]-3-iodo-5-methoxyphenyl)-1-ethanone C17H16ClIO3S 详情 详情
(XV) 27952 1-(4-[2-[(4-chlorophenyl)sulfanyl]ethoxy]-3-iodo-5-methoxyphenyl)-3-(dimethylamino)-1-propanone C20H23ClINO3S 详情 详情
(XVI) 27953 3-(4-[2-[(4-chlorophenyl)sulfanyl]ethoxy]-3-iodo-5-methoxyphenyl)-N,N,N-trimethyl-3-oxo-1-propanaminium iodide C21H26ClI2NO3S 详情 详情
(XVII) 27954 1-(4-[2-[(4-chlorophenyl)sulfanyl]ethoxy]-3-iodo-5-methoxyphenyl)-2-propen-1-one C18H16ClIO3S 详情 详情
(XVIII) 11136 3,4,5-Trimethoxybenzaldehyde 86-81-7 C10H12O4 详情 详情
(XIX) 27955 1-(4-[2-[(4-chlorophenyl)sulfanyl]ethoxy]-3-iodo-5-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione C28H28ClIO7S 详情 详情
(XX) 27956 1-(4-[2-[(4-chlorophenyl)sulfanyl]ethoxy]-3-iodo-5-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanediol C28H32ClIO7S 详情 详情
(XXI) 27957 2-(4-[2-[(4-chlorophenyl)sulfanyl]ethoxy]-3-iodo-5-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran C28H30ClIO6S 详情 详情
Extended Information