dimethyl (Z)-2-(3,4,5-trimethyl-1H-pyrrol-2-yl)but-2-enedioate | 76729-50-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl (Z)-2-(3,4,5-trimethyl-1H-pyrrol-2-yl)but-2-enedioate
• CAS: 76729-50-5
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: ZEYVMECUJJQIEO-POHAHGRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  反-3-(二甲氨基)丙烯腈 、 dimethyl (Z)-2-(3,4,5-trimethyl-1H-pyrrol-2-yl)but-2-enedioate 以 乙腈 为溶剂， 生成 dimethyl 6-cyano-1,2,3-trimethylindolizine-7,8-dicarboxylate
  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 、 丁炔二酸二甲酯 以 Petroleum ether 、 苯 为溶剂， 生成 dimethyl (Z)-2-(3,4,5-trimethyl-1H-pyrrol-2-yl)but-2-enedioate
  参考文献：
  名称：

  2-Addition of pyrroles to dimethyl acetylenedicarboxylate: Michael-type adducts and Diels-Alder products

  摘要：

  DOI：

  10.1021/jo01311a004

文献信息

• NOLAND W. E.; LEE CHANG KIU, J. ORG. CHEM., 1980, 45, NO 23, 4573-4582
  作者：NOLAND W. E.、 LEE CHANG KIU

  DOI：——

  日期：——
• 2-Addition of pyrroles to dimethyl acetylenedicarboxylate: Michael-type adducts and Diels-Alder products
  作者：Wayland E. Noland、Chang Kiu Lee

  DOI：10.1021/jo01311a004

  日期：1980.11
• 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.