methyl (E)-4-(3,4-dichlorophenyl)-4-oxo-2-butenoate -Drug Synthesis Database

【结构式】

【分子编号】18326

【品名】methyl (E)-4-(3,4-dichlorophenyl)-4-oxo-2-butenoate

【CA登记号】

【分子式】C₁₁H₈Cl₂O₃

【分子量】259.08812

【元素组成】C 50.99% H 3.11% Cl 27.37% O 18.53%

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：(I)

Conjugate addition of benzylmagnesium chloride (II) to unsaturated ketone (I) in the presence of cuprous iodide-dimethyl sulfide complex afforded the 2-benzyl derivative (III). Then, the ester function was saponified with NaOH in MeOH to give the title acid. Resolution of the enantiomers was effected by fractional crystallization of the ephedrine salts.

参考文献中间体

合成目标

【1】 Giordani, A.; Pevarello, P.; Cini, M.; Bormetti, R.; Greco, F.; Toma, S.; Speciale, C.; Varasi, M.; 4-Phenyl-4-oxo-butanoic acid derivatives inhibitors of kynurenine 3-hydroxylase. Bioorg Med Chem Lett 1998, 8, 20, 2907.

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)	18326	methyl (E)-4-(3,4-dichlorophenyl)-4-oxo-2-butenoate		C₁₁H₈Cl₂O₃	详情	详情
(II)	18327	benzyl(chloro)magnesium	6921-34-2	C₇H₇ClMg	详情	详情
(III)	18328	methyl 2-benzyl-4-(3,4-dichlorophenyl)-4-oxobutanoate		C₁₈H₁₆Cl₂O₃	详情	详情

Extended Information