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2012 , Vol. 32 >Issue 01: 104 - 112

DOI: https://doi.org/10.6023/cjoc1106302

研究论文

5-烷氧基-3,4-二卤-2(5H)-呋喃酮与脂肪胺类的反应研究

  • 傅建花 ,
  • 汪朝阳 ,
  • 霍景沛 ,
  • 谭越河 ,
  • 曾荣华
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  • 华南师范大学化学与环境学院 广州 510006

收稿日期: 2011-06-30

  修回日期: 2011-08-29

  网络出版日期: 2011-09-21

基金资助

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

收起

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

  • FU Jian-Hua ,
  • WANG Chao-Yang ,
  • HUO Jing-Pei ,
  • TAN Yue-He ,
  • ZENG Rong-Hua
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  • School of Chemistry and Environment, South China Normal University, Guangzhou 510006

Received date: 2011-06-30

  Revised date: 2011-08-29

  Online published: 2011-09-21

Supported by

Project supported by the the National Natural Science Foundation of China (No. 20772035), the Natural Science of Foundation of Guangdong Provine (No. 5300082) and the 3rd Talents Special Funds of Guangdong Higher Education (No. [2011]431).

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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.

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

本文引用格式

傅建花 , 汪朝阳 , 霍景沛 , 谭越河 , 曾荣华 . 5-烷氧基-3,4-二卤-2(5H)-呋喃酮与脂肪胺类的反应研究[J]. 有机化学, 2012 , 32(01) : 104 -112 . DOI: 10.6023/cjoc1106302

Abstract

Using KF as catalyst and tetrahydrofuran as solvent, 5-alkyloxy-3,4-dihalo-2(5H)-furanones was reacted with several 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 formation of 2(5H)-furanone ring-opening products involving in the rearrangement reaction was proposed.

Key words： 5-alkoxy-3,4-dihalo-2(5H)-furanone; aliphatic saturated secondary amine; tandem Michael addition-elinmination reaction; β-amino-2(5H)-furanone; ring-opening rearrangement reaction

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