三氯化铁催化合成2,3-二氢苯并色原酮  

Ferric Chloride Catalyzed Synthesis of 2,3-Dihydrobenzo[f]chromen-1-one

作　　者：丁晓友 徐凡[1] Ding Xiaoyou;Xu Fan(College of Chemistry,Chemical Engineering and Materials Science,Sooehow University,Suzhou 215123)

机构地区：[1]苏州大学材料与化学化工学部,苏州215123

出　　处：《有机化学》2018年第12期3345-3350,共6页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21272168)资助项目~~

摘　　要：芳并吡喃-4-酮骨架存在于许多天然及合成的生物活性物质中,因此发展其高效合成方法极具实用价值.本工作以氯化铁为催化剂催化3-甲基巴豆酸萘酯转化生成一系列2,3-二氢苯并色原酮,由原料通过发生Fries重排/氢烷氧化串联反应生成目标化合物.该方法所用催化剂价廉易得,转化效率较高,为合成芳并吡喃-4-酮类化合物提供了一种经济,实用和高效的新方法.Aromatic-fused pyran-4-one skeleton exists in many natural and synthetic biologically active materials. An efficient method for the transformation of naphthyl 3-methylcrotonate to 2,3-dihydro-benzo[f]chromen-1-one catalyzed by ferric chloride is described, which provides a practical process to afford this type of biologically important compounds in good yields using commercially available and inexpensive catalyst. A two-step mechanism involving Fries rearrangement and intramolecular hydroalkoxylation is proposed.

关 键 词：三氯化铁 芳并吡喃酮 催化 FRIES重排 氢烷氧化反应 

分 类 号：O626[理学—有机化学]