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【结 构 式】

【分子编号】26256

【品名】3-[(4-phenoxyphenyl)sulfanyl]cyclohexanol

【CA登记号】

【 分 子 式 】C18H20O2S

【 分 子 量 】300.4216

【元素组成】C 71.96% H 6.71% O 10.65% S 10.67%

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)

Michael addition of 4-(phenoxy)thiophenol (II) to cyclohexenone (I) afforded the ketosulfide (III). This was reduced with NaBH4 to give a diastereomeric mixture of alcohols (IV). Subsequent oxidation of sulfide group of (IV) with Oxone provided sulfone (V). Condensation with potassium thioacetate under Mitsunobu conditions gave the corresponding thioester as a mixture of isomers, from which the major trans isomer (VI) was isolated by chromatography. Finally, deprotection of (VI) with sodium methoxide in MeOH yielded the target thiol.

1 Mischke, B.V.; Freskos, J.N.; Stevens, A.M.; Mullins, P.B.; McDonald, J.J.; Stegeman, R.A.; Shieh, H.-S.; Synthesis and identification of conformationally constrained selective MMP inhibitors. Bioorg Med Chem Lett 1999, 9, 13, 1757.
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) 26253 2-cyclohexen-1-one;Cyclohex-2-enone;2-cyclohexenone 930-68-7 C6H8O 详情 详情
(II) 26254 4-phenoxybenzenethiol; 4-phenoxyphenylhydrosulfide C12H10OS 详情 详情
(III) 26255 3-[(4-phenoxyphenyl)sulfanyl]cyclohexanone C18H18O2S 详情 详情
(IV) 26256 3-[(4-phenoxyphenyl)sulfanyl]cyclohexanol C18H20O2S 详情 详情
(V) 26257 3-[(4-phenoxyphenyl)sulfonyl]cyclohexanol C18H20O4S 详情 详情
(VI) 26258 S-[(1S,3S)-3-[(4-phenoxyphenyl)sulfonyl]cyclohexyl] ethanethioate C20H22O4S2 详情 详情
Extended Information