methyl 4-[(Z)-2-phenylethenyl]phenyl sulfone -Drug Synthesis Database

【结构式】

【分子编号】26586

【品名】methyl 4-[(Z)-2-phenylethenyl]phenyl sulfone

【CA登记号】

【分子式】C₁₅H₁₄O₂S

【分子量】258.34096

【元素组成】C 69.74% H 5.46% O 12.39% S 12.41%

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：(XII)

An related procedure was based on the formation of the intermediate stilbene sulfone (XII) by Wittig reaction. Thus, condensation of phosphonium salt (IX) with aldehyde (X) in the presence of LiOEt gave stilbene (XI) as a mixture of geometric isomers. Then, oxidation of the sulfide group of (XI) with Oxone provided stilbene sulfone (XII). Alternatively, phosphonium salt (XIV), prepared from benzyl chloride (XIII) and triphenyl phosphine, was condensed with benzaldehyde to yield (XII). The oxidation of stilbene (XII) with KMnO4 produced benzil (XV). Finally, cyclization of (XV) with hemiacetal (VII) furnished the title imidazole.

参考文献中间体

合成目标

【1】 Barta, T.E.; Collins, P.W.; Weier, R.M.; Stealey, M.A.; Antiinflammatory 4,5-diarylimidazoles as selective cyclooxygenase inhibitors. Bioorg Med Chem Lett 1998, 8, 24, 3443.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	10498	Benzaldehyde;Benzoic aldehyde;Phenylmethanal	100-52-7	C₇H₆O	详情	详情
(VII)	26582	1-ethoxy-2,2,2-trifluoro-1-ethanol	433-27-2	C₄H₇F₃O₂	详情	详情
(IX)	26584	benzyl(triphenyl)phosphonium iodide	15853-35-7	C₂₅H₂₂IP	详情	详情
(X)	18815	4-(methylsulfanyl)benzaldehyde; 4-(methylmercapto)benzaldehyde	3446-89-7	C₈H₈OS	详情	详情
(XI)	26585	methyl 4-[(Z)-2-phenylethenyl]phenyl sulfide		C₁₅H₁₄S	详情	详情
(XII)	26586	methyl 4-[(Z)-2-phenylethenyl]phenyl sulfone		C₁₅H₁₄O₂S	详情	详情
(XIII)	26587	4-(chloromethyl)phenyl methyl sulfone		C₈H₉ClO₂S	详情	详情
(XIV)	26588	[4-(methylsulfonyl)benzyl](triphenyl)phosphonium chloride		C₂₆H₂₄ClO₂PS	详情	详情
(XV)	26589	1-[4-(methylsulfonyl)phenyl]-2-phenyl-1,2-ethanedione		C₁₅H₁₂O₄S	详情	详情

Extended Information