【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