2-[[(4-phenoxyphenyl)sulfonyl]methyl]oxirane; 2-oxiranylmethyl 4-phenoxyphenyl sulfone -Drug Synthesis Database

【结构式】

【分子编号】46033

【品名】2-[[(4-phenoxyphenyl)sulfonyl]methyl]oxirane; 2-oxiranylmethyl 4-phenoxyphenyl sulfone

【CA登记号】

【分子式】C₁₅H₁₄O₄S

【分子量】290.33976

【元素组成】C 62.05% H 4.86% O 22.04% S 11.04%

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：(VII)

Treatment of 4-phenoxyphenol (I) with N,N-dimethylthiocarbamoyl chloride afforded the O-aryl thiocarbamate (II), which was thermally rearranged to the S-aryl thiocarbamate (III). Basic hydrolysis of (III) provided 4-phenoxythiophenol (IV). Subsequent alkylation of (IV) with allyl bromide (V) led to the allyl thioether (VI). Further oxidation of (VI) with m-chloroperbenzoic acid (MCPBA) gave rise to the epoxisulfone (VII). This was finally converted to the target thiirane derivative upon treatment with ammonium thiocyanate.

参考文献中间体

合成目标

【1】 Kotra, L.P.; Brown, S.; Bernardo, M.M.; Tanaka, Y.; Li, Z.-H.; Fridman, R.; Mobashery, S.; Potent and selective mechanism-based inhibition of gelatinases. J Am Chem Soc 2000, 122, 28, 6799.
【2】 Mobashery, S.; Fridman, R. (Wayne State University); Inhibitors of matrix metalloproteinases. WO 0192244 .

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)	27080	4-Phenoxyphenol	831-82-3	C₁₂H₁₀O₂	详情	详情
(II)	27081	O-(4-phenoxyphenyl) dimethylcarbamothioate		C₁₅H₁₅NO₂S	详情	详情
(III)	46031	S-(4-phenoxyphenyl) dimethylcarbamothioate		C₁₅H₁₅NO₂S	详情	详情
(IV)	26254	4-phenoxybenzenethiol; 4-phenoxyphenylhydrosulfide		C₁₂H₁₀OS	详情	详情
(V)	11463	3-Bromo-1-propene; 3-Bromopropene；allyl bromide	106-95-6	C₃H₅Br	详情	详情
(VI)	46032	1-(allylsulfanyl)-4-phenoxybenzene; 4-(allylsulfanyl)phenyl phenyl ether		C₁₅H₁₄OS	详情	详情
(VII)	46033	2-[[(4-phenoxyphenyl)sulfonyl]methyl]oxirane; 2-oxiranylmethyl 4-phenoxyphenyl sulfone		C₁₅H₁₄O₄S	详情	详情

Extended Information