3,4-diphenyl-pyrrole-1-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3,4-diphenyl-pyrrole-1-carboxylic acid ethyl ester
• 英文别名: Ethyl 3,4-diphenylpyrrole-1-carboxylate
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: OEMZRRFUSFZVMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1Z,3Z)-2,3-diphenyl-1,4-diiodo-1,3-butadiene 、 氨基甲酸乙酯 在 copper(l) iodide 、 caesium carbonate 、 (1R,2R)-(-)-N,N'-二甲基-1,2-环己二胺 作用下， 以 1,4-二氧六环 为溶剂， 以80%的产率得到3,4-diphenyl-pyrrole-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Copper-catalyzed synthesis of five-membered heterocycles via double C–N bond formation: an efficient synthesis of pyrroles, dihydropyrroles, and carbazoles

  摘要：

  An efficient copper-catalyzed double C-N bond forming reaction using diiodides and nitrogen-centered nucleophiles including amides and carbamates is reported. The reactions proceed to afford di- or tri-substituted N-acylpyrroles, dihydropyrroles, and carbazoles in good to excellent yields when different such as 1,4-diiodo-1,3-butadienes, 1,4-dihalobut-1-enes, and 2,2'-diiodobiphenyls were employed, respectively. It is crucial to use CuI as the catalyst with the assistance of proper base and diamine ligand. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.075

文献信息

• Copper-Catalyzed Double <i>N</i>-Alkenylation of Amides:  An Efficient Synthesis of Di- or Trisubstituted <i>N</i>-Acylpyrroles
  作者：Xiyuan Yuan、Xiaobing Xu、Xiaobo Zhou、Jiwei Yuan、Lugen Mai、Yanzhong Li

  DOI：10.1021/jo062194s

  日期：2007.2.1

  An efficient copper-catalyzed double alkenylation of amides with (1Z,3Z)-1,4-diiodo-1,3-dienes is reported for the first time. The reactions proceed to afford di- or trisubstituted N-acylpyrroles in good to excellent yields using CuI as the catalyst, Cs2CO3 as the base, and rac-trans-N,N'-dimethylcyclohexane-1,2-diamine as the ligand.
• Copper-catalyzed synthesis of five-membered heterocycles via double C–N bond formation: an efficient synthesis of pyrroles, dihydropyrroles, and carbazoles
  作者：Ende Li、Xiaobing Xu、Hongfeng Li、Huimin Zhang、Xiaolei Xu、Xiyuan Yuan、Yanzhong Li

  DOI：10.1016/j.tet.2009.08.075

  日期：2009.10

  An efficient copper-catalyzed double C-N bond forming reaction using diiodides and nitrogen-centered nucleophiles including amides and carbamates is reported. The reactions proceed to afford di- or tri-substituted N-acylpyrroles, dihydropyrroles, and carbazoles in good to excellent yields when different such as 1,4-diiodo-1,3-butadienes, 1,4-dihalobut-1-enes, and 2,2'-diiodobiphenyls were employed, respectively. It is crucial to use CuI as the catalyst with the assistance of proper base and diamine ligand. (C) 2009 Elsevier Ltd. All rights reserved.