2-(1,3-benzodioxol-5-yl)-4-(4-methoxyphenyl)-4-oxobutanenitrile -Drug Synthesis Database

【结构式】

【分子编号】25776

【品名】2-(1,3-benzodioxol-5-yl)-4-(4-methoxyphenyl)-4-oxobutanenitrile

【CA登记号】

【分子式】C₁₈H₁₅NO₄

【分子量】309.32144

【元素组成】C 69.89% H 4.89% N 4.53% O 20.69%

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)

Aldol condensation of piperonal (I) with 4-methoxyacetophenone (II) afforded chalcone (III). Subsequent addition of KCN to (III) in the presence of AcOH gave nitrile (IV), which was hydrolyzed in methanol in the presence of p-TsOH to provide ketoester (V). Subsequent base-catalyzed condensation of (V) with aldehyde (VI), followed by cyclization in refluxing AcOH furnished the target butenolide.

参考文献中间体

合成目标

【1】 Repine, J.T.; Patt, W.C.; Cheng, X.-M.; et al.; Butenolide endothelin antagonists with improved aqueous solubility. J Med Chem 1999, 42, 12, 2162.

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)	10127	1,3-Benzodioxole-5-carbaldehyde; Heliotropine	120-57-0	C₈H₆O₃	详情	详情
(II)	11041	4-Methoxyacetophenone; 1-(4-Methoxyphenyl)-1-ethanone	100-06-1	C₉H₁₀O₂	详情	详情
(III)	25775	(E)-3-(1,3-benzodioxol-5-yl)-1-(4-methoxyphenyl)-2-propen-1-one		C₁₇H₁₄O₄	详情	详情
(IV)	25776	2-(1,3-benzodioxol-5-yl)-4-(4-methoxyphenyl)-4-oxobutanenitrile		C₁₈H₁₅NO₄	详情	详情
(V)	25777	ethyl 2-(1,3-benzodioxol-5-yl)-4-(4-methoxyphenyl)-4-oxobutanoate		C₂₀H₂₀O₆	详情	详情
(VI)	25778	3-(5-formyl-2,3-dimethoxyphenoxy)-1-propanesulfonate		C₁₂H₁₅O₇S	详情	详情

Extended Information