5-烷氧基-3,4-二卤-2(5H)-呋喃酮与脂肪胺类的反应研究  

Research on the Reaction of 5-Alkyloxy-3,4-dihalo-2(5H)-furanones with Aliphatic Amines

作　　者：傅建花[1] 汪朝阳[1] 霍景沛[1] 谭越河[1] 曾荣华[1] 

机构地区：[1]华南师范大学化学与环境学院,广州510006

出　　处：《有机化学》2012年第1期104-112,共9页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.20772035);广东省自然科学基金(No.5300082);广东省高等学校人才引进专项基金(No.[2011]431)资助项目~~

摘　　要：在氟化钾作催化剂和四氢呋喃作溶剂的条件下,研究了系列脂肪胺亲核试剂与5-烷氧基-3,4-二卤-2(5H)-呋喃酮发生的反应,通过旋光度,UV-Vis,IR,1H NMR,13C NMR,MS,元素分析和X射线单晶衍射等表征方法对产物进行结构表征,发现通常情况下发生预期的串联迈克尔加成-消除反应,合成了13个新的β-胺基-2(5H)-呋喃酮.但是,空间位阻较大的二环己基胺与5-烷氧基-3,4-二卤-2(5H)-呋喃酮反应时,却得到了4个异常的2(5H)-呋喃酮开环产物,其可能是经开环重排反应的机理得到的.Using KF as catalyst and tetrahydrofuran as solvent,5-alkyloxy-3,4-dihalo-2（5H）-furanones was reacted with sev-eral aliphatic amines.The chemical structures and absolute configurations of the products were confirmed via rotation,UV-Vis,IR,1H NMR,13C NMR,MS techniques,elemental analysis and X-ray single crystal diffraction.Thirteen new normal products β-amino-2（5H）-furanones were obtained via the tandem Michael addition-elimination reaction as anticipated in most cases.However,the reaction between the larger steric dicyclohexyl amine and 5-alkyloxy-3,4-dihalo-2（5H）-furanones yielded four new abnormal products,（E）-alkyl 2-halo-4-dicyclohexylamino-4-oxobut-2-enoate.The possible mechanism for the for-mation of 2（5H）-furanone ring-opening products involving in the rearrangement reaction was proposed.

关 键 词：5-烷氧基-3 4-二卤-2(5H)-呋喃酮 脂肪族仲胺 串联迈克尔加成-消除反应 β-胺基-2(5H)-呋喃酮 开环重排反应 

分 类 号：O621.25[理学—有机化学]