3-[(4-phenoxyphenyl)sulfanyl]cyclohexanone -Drug Synthesis Database

【结构式】

【分子编号】26255

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

【CA登记号】

【分子式】C₁₈H₁₈O₂S

【分子量】298.40572

【元素组成】C 72.45% H 6.08% O 10.72% S 10.75%

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：(III)

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.

参考文献中间体

合成目标

【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