6,7-dimethoxy-3-(4-methylphenyl)-2H-chromen-2-one -Drug Synthesis Database

【结构式】

【分子编号】64842

【品名】6,7-dimethoxy-3-(4-methylphenyl)-2H-chromen-2-one

【CA登记号】

【分子式】C₁₈H₁₆O₄

【分子量】296.32264

【元素组成】C 72.96% H 5.44% O 21.6%

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)

Partial demethylation of 2,4,5-trimethoxybenzaldehyde (I) with BCl3 gives 2-hydroxy-4,5-dimethoxybenzaldehyde (II), which is condensed with the sodium salt of p-tolylacetic acid (III) in boiling acetic anhydride to afford the coumarin derivative (IV). Benzylic halogenation of (IV) with N-bromosuccinimide in the presence of a catalytic amount of benzoyl peroxide yields bromide (V), which is finally condensed with N-methyl benzylamine (VI) to afford the desired compound.

参考文献中间体

合成目标

【1】 Piazzi, L.; Rampa, A.; Bisi, A.; Gobbi, S.; Belluti, F.; Cavalli, A.; Bartolini, M..; Andrisano, V.; Valenti, P.; Recanatini, M.; 3-(4-{[Benzyl(methyl)amino]methyl}phenyl)-6,7-dimethoxy-2H-2-chromenone (AP2238) inhibits both acetylcholinesterase and acetylcholinesterase-induced beta-amyloid aggregation: A dual function lead for Alzheimer's disease therapy. J Med Chem 2003, 46, 12, 2279.

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)	64839	2,4,5-trimethoxybenzaldehyde		C₁₀H₁₂O₄	详情	详情
(II)	64840	2-hydroxy-4,5-dimethoxybenzaldehyde		C₉H₁₀O₄	详情	详情
(III)	64841	sodium 2-(4-methylphenyl)acetate		C₉H₉NaO₂	详情	详情
(IV)	64842	6,7-dimethoxy-3-(4-methylphenyl)-2H-chromen-2-one		C₁₈H₁₆O₄	详情	详情
(V)	64843	3-[4-(bromomethyl)phenyl]-6,7-dimethoxy-2H-chromen-2-one		C₁₈H₁₅BrO₄	详情	详情
(VI)	11969	N-Methyl(phenyl)methanamine; N-Benzyl-N-methylamine; N-Methylbenzylamine	103-67-3	C₈H₁₁N	详情	详情

Extended Information