methyl 4-benzyl-5-phenyl-2-prop-2-enyl-1H-pyrrole-3-carboxylate | 1189516-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 4-benzyl-5-phenyl-2-prop-2-enyl-1H-pyrrole-3-carboxylate
• CAS: 1189516-82-2
• 化学式: C₂₂H₂₁NO₂
• 分子量: 331.414
• InChiKey: AVWZLQAERVQPSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Methyl 3-benzyl-2-cyano-4-oxo-4-phenylbutanoate 、 3-溴丙烯 在 indium 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以52%的产率得到methyl 4-benzyl-5-phenyl-2-prop-2-enyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  An expedient synthesis of poly-substituted pyrroles from γ-ketonitriles via indium-mediated Barbier reaction strategy

  摘要：

  We developed an efficient synthetic strategy of poly-substituted pyrroles via an indium-mediated Barbier type allylation from gamma-ketonitriles. Initial attack of allylindium species occurred at the nitrile group selectively to form the enamine intermediate, which reacted with the ketone group intramolecularly to furnish the pyrroles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.140

文献信息

• An expedient synthesis of poly-substituted pyrroles from γ-ketonitriles via indium-mediated Barbier reaction strategy
  作者：Sung Hwan Kim、Se Hee Kim、Ka Young Lee、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2009.07.140

  日期：2009.10

  We developed an efficient synthetic strategy of poly-substituted pyrroles via an indium-mediated Barbier type allylation from gamma-ketonitriles. Initial attack of allylindium species occurred at the nitrile group selectively to form the enamine intermediate, which reacted with the ketone group intramolecularly to furnish the pyrroles. (C) 2009 Elsevier Ltd. All rights reserved.