高等学校化学学报

高等学校化学学报 ›› 2000, Vol. 21 ›› Issue (1): 74.

• 论文 • 上一篇    下一篇

一个改进的Dallacker双内酯的合成

付滨, 赵晨, 张滂   

  1. 北京大学化学与分子工程学院, 北京 100871
  • 收稿日期:1999-04-26 出版日期:2000-01-24 发布日期:2000-01-24
  • 通讯作者: 张　滂(1917年出生),男,博士,教授,中国科学院院士,从事有机合成研究.
  • 基金资助:

    国家自然科学基金(批准号:29572035);教育部博士学科点基金资助

A Facile Synthesis of Dallacker Bislactone

FU Bin, ZHAO Chen, ZHANG Pang   

  1. College of Chemical and Molecular Engineering, Peking University, Beijing 100871, China
  • Received:1999-04-26 Online:2000-01-24 Published:2000-01-24

PDF (PC)

被引次数

7

摘要： 以5步反应从邻碘苯甲酸乙酯合成了9,10-二氢-9,9,10,10-双(γ-丁内酯)菲,减少了3步反应,总产率提高7%.又由邻碘苯甲酰氯与乙烷-1,1,2-三羧酸三乙酯缩合,继以消除两个乙酯基合成Dallacker双内酯,反应减少一步,产率则增高13%.还研究了联苯-2,2-二甲酰氯分别与乙烷-1,1,2-三羧酸三乙酯和氰基琥珀酸二乙酯的缩合,均能得到良好的产率.

关键词: 二氢菲双内酯, 苝醌, McMurry反应

Abstract: Dihydro-9,9,10,10-bis(propiono-γ-lactono)-phenanthrene was synthesized by five steps of reaction with an overall yield of 24%, 7% better than Dallacker synthesis in eight steps. Ethyl 3-(o-iodobenzoyl)propionate was also synthesized from o-iodobenzoyl chloride and triethyl ethane-1,1,2-tricarboxylate in two steps of reaction with an overall yield of 43%, 13% better than the above synthesis. The acylation of triethyl ethane-1,1,2-tri-carboxylate by diphenoyl chloride was also studied and reasonably good yields obtained.

Key words: Dihydrophenanthrenebislactone, Perylenequinone, McMurry reaction

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