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【结 构 式】

【分子编号】27802

【品名】1-[4-(benzyloxy)-2-hydroxy-6-methoxyphenyl]-1-ethanone

【CA登记号】

【 分 子 式 】C16H16O4

【 分 子 量 】272.30064

【元素组成】C 70.57% H 5.92% O 23.5%

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)

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.

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