(E)-2-(3,4,5-trimethyl-1H-pyrrol-2-yl)but-2-enedinitrile | 202596-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (E)-2-(3,4,5-trimethyl-1H-pyrrol-2-yl)but-2-enedinitrile
• CAS: 202596-40-5
• 化学式: C₁₁H₁₁N₃
• 分子量: 185.228
• InChiKey: QISUZRAKVVOUJS-WMZJFQQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  反-3-(二甲氨基)丙烯腈 、 (E)-2-(3,4,5-trimethyl-1H-pyrrol-2-yl)but-2-enedinitrile 以 乙腈 为溶剂， 生成 6,7,8-tricyano-1,2,3-trimethylindolizine
  参考文献：
  名称：

  Electrochemically Induced Hetero-[4+2]-Cycloaddition Reactions Between 2-Vinylpyrroles andβ-Acceptor-Substituted Enamines

  摘要：

  Recently, we reported on radical cation cycloaddition reactions between 2-vinylindoles and beta-acceptor-substituted enamines, which provide a new pathway to pyrido[1,2-a] indoles.([1]) In order to broaden the synthetic scope of this reaction, we have developed hetero-[4+2]-cycloaddition reactions between a number of readily accessible 2-vinylpyrroles, acting as heterodienes, and beta-acceptor-substituted enamines. This reaction is induced by electrochemically generated radical cations of either the 2-vinylpyrrole diene or the enamine dienophile. These electron-transfer-induced reactions open up a novel route to highly substituted indolizines in moderate yields. We propose a mechanism that explains both the complete regio-control of this cycloaddition as well as the product formation, irrespective of the inducing radical cation species.

  DOI：

  10.1002/(sici)1521-3765(199801)4:1<107::aid-chem107>3.0.co;2-e
• 作为产物：
  描述：

  2,3,4-三甲基-1H-吡咯 、 丁烷-1,4-二胺 以 四氢呋喃 为溶剂， 反应 1.0h， 以9%的产率得到(Z)-2-(3,4,5-trimethyl-1H-pyrrol-2-yl)but-2-enedinitrile
  参考文献：
  名称：

  Electrochemically Induced Hetero-[4+2]-Cycloaddition Reactions Between 2-Vinylpyrroles andβ-Acceptor-Substituted Enamines

  摘要：

  Recently, we reported on radical cation cycloaddition reactions between 2-vinylindoles and beta-acceptor-substituted enamines, which provide a new pathway to pyrido[1,2-a] indoles.([1]) In order to broaden the synthetic scope of this reaction, we have developed hetero-[4+2]-cycloaddition reactions between a number of readily accessible 2-vinylpyrroles, acting as heterodienes, and beta-acceptor-substituted enamines. This reaction is induced by electrochemically generated radical cations of either the 2-vinylpyrrole diene or the enamine dienophile. These electron-transfer-induced reactions open up a novel route to highly substituted indolizines in moderate yields. We propose a mechanism that explains both the complete regio-control of this cycloaddition as well as the product formation, irrespective of the inducing radical cation species.

  DOI：

  10.1002/(sici)1521-3765(199801)4:1<107::aid-chem107>3.0.co;2-e

文献信息

• Electrochemically Induced Hetero-[4+2]-Cycloaddition Reactions Between 2-Vinylpyrroles andβ-Acceptor-Substituted Enamines
  作者：Thomas Peglow、Siegfried Blechert、Eberhard Steckhan

  DOI：10.1002/(sici)1521-3765(199801)4:1<107::aid-chem107>3.0.co;2-e

  日期：1998.1

  Recently, we reported on radical cation cycloaddition reactions between 2-vinylindoles and beta-acceptor-substituted enamines, which provide a new pathway to pyrido[1,2-a] indoles.([1]) In order to broaden the synthetic scope of this reaction, we have developed hetero-[4+2]-cycloaddition reactions between a number of readily accessible 2-vinylpyrroles, acting as heterodienes, and beta-acceptor-substituted enamines. This reaction is induced by electrochemically generated radical cations of either the 2-vinylpyrrole diene or the enamine dienophile. These electron-transfer-induced reactions open up a novel route to highly substituted indolizines in moderate yields. We propose a mechanism that explains both the complete regio-control of this cycloaddition as well as the product formation, irrespective of the inducing radical cation species.