高等学校化学学报

高等学校化学学报 ›› 1997, Vol. 18 ›› Issue (8): 1312.

• 论文 • 上一篇    下一篇

3,5-二甲氧基苯乙醛和丙二酸单乙酯的Knoevenagel缩合

赵亚军, 焦玉国, 唐恢同, 张滂   

  1. 北京大学化学系, 北京 100871
  • 收稿日期:1996-12-24 出版日期:1997-08-24 发布日期:1997-08-24
  • 通讯作者: 张滂
  • 作者简介:赵亚军, 男, 34岁, 博士, 副教授.
  • 基金资助:

    国家自然科学基金;国家教育委员会博士学科点基金

Knoevenagel Condensation of 3,5-Dimethoxyphenylacetaldehyde with Ethyl Hydrogen Malonate

ZHAO Ya-Jun, JIAO Yu-Guo, TANG Hui-Tong, ZHANG Pang   

  1. Department of Chemistry, Peking University, Beijing 100871
  • Received:1996-12-24 Online:1997-08-24 Published:1997-08-24

PDF (PC)

被引次数

10

摘要： 从3,5-二甲基苯乙醛和丙二酸单乙酯的Knoevenagel缩合反应得到2个产物,其一经证实是重排生成的4－(3,5-二甲氧苯基)-3-丁烯酸乙酯,另一个是2',4',2",4"-四甲氧基-2,3：6,7-二苯并-9-氧杂双环［3.3.1］壬-2,6－二烯.经元素分析、IR、NMR、MS和X射线衍射证实前者不发生可逆重排为其2-烯酸酯异构体的反应.

关键词: Knoevenagel缩合, 4-苯基丁烯酸酯重排, 4-(3, 5-二甲氧苯基)-3-丁烯酸乙酯, 二苯并-9-氧杂双环[3.3.1]壬-2, 6-二烯衍生物

Abstract: Knoevenagel condensation of 3,5-dimethoxyphenylacetaldehyde with ethyl hydro-gen malonate in pyridine-piperidine led to the isolation of two products. One is not the ex-pected 4-(3, 5-dimethoxyphenyl)-2-butenoate,but is its isomeric 3-butenoate which could not be equilibrated with its 2-isomer by a base like its parent 4-phenyl-2-and-3-butenoates.The other is 2', 4', 2", 4"-tetramethoxy-2, 3: 6, 7-dibenzo-9-oxabicyclo [3.3.1]nona-2, 6-di-ene which is formed by phenol-aldehyde condensation under the basic condition rather than usual dimerization brought about by Lewis acid catalysis.

Key words: Knoevenagel condensation, 4-Phenylbutenoate rearrangement, 4-(3,5-Dimethoxyphenyl)-3-butenoate, 9-Oxabicyclo[3.3.1]nonane

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