四丁基碘化铵催化合成螺[4.4]壬烷-1,6-二酮  

Synthesis of Spir[4.4]ononane-1,6-dione Catalyzed by Tetrabutylammonium Iodide

作　　者：张万轩[1] 田露[1] 刘丽琴[1] 王俊[1] 

机构地区：[1]湖北大学有机功能分子合成与应用教育部重点实验室,湖北武汉430062

出　　处：《化学与生物工程》2010年第9期21-22,65,共3页Chemistry & Bioengineering

基　　金：国家自然科学基金资助项目(20872031);湖北省教育厅优秀中青年科技创新团队资助项目(T200701)

摘　　要：改进了螺[4.4]壬烷-1,6-二酮的合成方法。以环戊酮-2-羧酸乙酯和4-溴丁酸乙酯为起始原料、四丁基碘化铵为催化剂、THF为溶剂、碳酸钾为碱,制备了4-(1-乙氧羰基-2-氧代环戊基)丁酸乙酯,产率达到87%。该反应条件温和,不需要在无水无氧条件下进行。4-(1-乙氧羰基-2-氧代环戊基)丁酸乙酯经水解脱羧和关环反应得到外消旋螺[4.4]壬烷-1,6-二酮。Ethyl 4-（1-ethoxycarbonyl-2-oxocyclopentyl）butanoate was prepared successfully from ethyl 2-oxocyclopentanecarboxylate and ethyl 4-bromobutanoate catalyzed by tetrabutylammonium iodide under mild conditions,with THF as solvent and K2CO3 as base.Spirononane-1,6-dione was synthesized by hydrolysis and decarboxylation of ethyl 4-（1-ethoxycarbonyl-2-oxocyclopentyl）butanoate followed by ring closure reaction.

关 键 词：环戊酮-2-羧酸乙酯 4-溴丁酸乙酯 4-(1-乙氧羰基-2-氧代环戊基)丁酸乙酯 四丁基碘化铵 合成 

分 类 号：TQ234.2[化学工程—有机化工]