摘要/Abstract

对8-羟基异香豆素的合成方法进行研究.以麦氏酸为原料，通过傅克酰基化，羰基保护，酯基还原，脱保护，得到关键中间体3-乙炔基-2-（羟甲基）环己-2-烯-1-酮，再经酸性环化加成，环己烯酮环的芳构化，2，3-二氯-5，6-二氰对苯醌（DDQ）氧化等步骤，合成得到8-羟基异香豆素.合成的化合物结构经过¹H NMR，¹³C NMR，IR，HRMS表征.
关键词: 异香豆素, 8-羟基异香豆素, 吡喃, 芳构化, 合成方法
A new method for the synthesis of 8-hydroxyisocoumarin is reported. 8-Hydroxyisocoumarin was synthesized from Meldrum's acid by Friedel-Crafts acylation, carbonyl protection, ester reduction and deprotection. The key intermediate 3-ethynyl-2-(hydroxymethyl)cyclohex-2-en-1-one was synthesized by acidic cycloaddition, aromatization of cyclohexanone ring and 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ) oxidation. The structures were characterized by ¹H NMR, ¹³C NMR, IR, and HRMS.
Key words: isocoumarin, 8-hydroxyisocoumarin, pyran, aromatization, synthetic method


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