(E)-1-[4-(benzyloxy)-2-hydroxy-6-methoxyphenyl]-3-(3,4-dimethoxyphenyl)-2-propen-1-one -Drug Synthesis Database

【结构式】

【分子编号】27803

【品名】(E)-1-[4-(benzyloxy)-2-hydroxy-6-methoxyphenyl]-3-(3,4-dimethoxyphenyl)-2-propen-1-one

【CA登记号】

【分子式】C₂₅H₂₄O₆

【分子量】420.46196

【元素组成】C 71.42% H 5.75% O 22.83%

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)

The condensation of 4-benzyloxy-2-hydroxy-6-methoxyacetophenone (I) with 3,4-dimethoxybenzaldehyde (II) by means of KOH in ethanol/water gives the chalcone (III), which is cyclized by means of SeO2 in refluxing isoamyl alcohol to yield the benzopyran (IV). The hydrogenolysis of the benzyl group of (IV) with H2 over Pd/C in chloroform affords the 7-hydroxybenzopyran (V), which is condensed with tert-butyl bromoacetate (VII) by means of CaCO3 in DMF to provide the benzopyranyloxy acetate (VIII). Finally, this compound is deprotected by reaction with p-toluenesulfonic acid in refluxing benzene.

参考文献中间体

合成目标

【1】 Yoo, M.; Son, M.W.; Kin, I.Y.; Kin, W.B.; Kin, S.H.; Lee, S.D.; Lim, G.J.; Lim, J.I.; Ahn, B.O.; Baik, N.G.; Kin, D.S.; Oh, T.Y.; Ryu, B.K.; Yang, J.S.; Shin, H.C. (Dong-A Pharmaceutical Co., Ltd.); Gastroprotective flavone/flavone cpds. with therapeutic effect on inflammatory bowel disease. JP 1999514015; US 6025387; WO 9804541 .

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)	27802	1-[4-(benzyloxy)-2-hydroxy-6-methoxyphenyl]-1-ethanone		C₁₆H₁₆O₄	详情	详情
(II)	18304	3,4-Dimethoxybenzaldehyde; Veratraldehyde	120-14-9	C₉H₁₀O₃	详情	详情
(III)	27803	(E)-1-[4-(benzyloxy)-2-hydroxy-6-methoxyphenyl]-3-(3,4-dimethoxyphenyl)-2-propen-1-one		C₂₅H₂₄O₆	详情	详情
(IV)	27804	7-(benzyloxy)-2-(3,4-dimethoxyphenyl)-5-methoxy-4H-chromen-4-one		C₂₅H₂₂O₆	详情	详情
(V)	27805	2-(3,4-dimethoxyphenyl)-7-hydroxy-5-methoxy-4H-chromen-4-one		C₁₈H₁₆O₆	详情	详情
(VI)	17430	2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate	5292-43-3	C₆H₁₁BrO₂	详情	详情
(VII)	27806	tert-butyl 2-[[2-(3,4-dimethoxyphenyl)-5-methoxy-4-oxo-4H-chromen-7-yl]oxy]acetate		C₂₄H₂₆O₈	详情	详情

Extended Information