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2022 , Vol. 42 >Issue 1: 181 - 189

DOI: https://doi.org/10.6023/cjoc202107043

研究论文

乙腈(丙酮)α-C嵌入合成2-取代环戊烯并[c]色烯衍生物

  • 钱宇亮 ,
  • 许岚 ,
  • 童义涵 ,
  • 刘天怿 ,
  • 夏盈盈 ,
  • 胡顶茂 ,
  • 荣良策
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  • 江苏师范大学化学与材料科学学院 江苏徐州 221116

收稿日期: 2021-07-19

  修回日期: 2021-09-05

  网络出版日期: 2021-09-15

基金资助

江苏省高校自然科学研究项目(18KJA150004); 大学生创新创业训练计划和江苏省高校品牌专业建设工程资助项目

收起

Synthesis of 2-Substituted Cyclopenta[c]chromene Derivatives by α-C Insertion of Acetonitrile (Acetone)

  • Yuliang Qian ,
  • Lan Xu ,
  • Yihan Tong ,
  • Tianyi Liu ,
  • Yingying Xia ,
  • Dingmao Hu ,
  • Liangce Rong
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  • School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
* Corresponding author. E-mail:

Received date: 2021-07-19

  Revised date: 2021-09-05

  Online published: 2021-09-15

Supported by

Natural Science Foundation of the Jiangsu Higher Education Institutions(18KJA150004); Undergraduate Innovation and Entrepreneurship Training Program, and the Brand Major of Universities in Jiangsu Province

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摘要

报道了氧联1,7-烯炔与乙腈、丙酮通过α-C嵌入方式合成2-取代环戊烯并[c]色烯衍生物. 本反应具有底物范围广、基团兼容性好及产率良好等优点. 研究表明这是一个自由基反应过程, 也是构建含氧杂环一个有效的方法. 产物2-氰基-3a,8-二甲基-1-对氟苯基-2,3,3a,4-四氢环戊烯并[c]色烯(3am)的晶体衍射分析进一步确定了产物的结构.

关键词： 自由基反应; 氧联1,7-烯炔; 色烯; 溴化亚铜

本文引用格式

钱宇亮 , 许岚 , 童义涵 , 刘天怿 , 夏盈盈 , 胡顶茂 , 荣良策 . 乙腈(丙酮)α-C嵌入合成2-取代环戊烯并[c]色烯衍生物[J]. 有机化学, 2022 , 42(1) : 181 -189 . DOI: 10.6023/cjoc202107043

Abstract

The efficient synthesis of 2-substituted cyclopenta[c]chromene derivatives was realized by α-C insertion of acetonitrile (acetone) with oxygen-linked 1,7-enynes catalyzed by cuprous bromide. The advantages of this reaction were wide range of substrates, high compatiblity of functional groups and good yield. The results showed that this was a radical reaction process, and it was also an effective way to construct oxygen-containing heterocycles. The X-ray diffraction analysis of 1-(4-fluorophenyl)-3a,8-dimethyl-2,3,3a,4-tetrahydrocyclopenta[c]chromene-2-carbonitrile (3am) further confirmed the structure of the product.

Key words： radical reaction; oxygen-linked 1,7-enyne; chromene; CuBr

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