ethyl E-3-(1-methyl-3-phenylindol-2-yl)acrylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl E-3-(1-methyl-3-phenylindol-2-yl)acrylate
• 英文别名: ethyl (E)-3-(1-methyl-3-phenylindol-2-yl)prop-2-enoate
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: JKGZAWGGJATGEV-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  3-(2-iodophenyl)indole 在 palladium diacetate sodium hydride 、 cesium pivalate 、 双二苯基膦甲烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl E-3-(1-methyl-3-phenylindol-2-yl)acrylate
  参考文献：
  名称：

  Aryl to Aryl Palladium Migration in the Heck and Suzuki Coupling of o-Halobiaryls

  摘要：

  A novel 1,4-palladium migration between the o- and o'-positions of biaryls has been observed in organopalladium intermediates derived from o-halobiaryls. The organopalladium intermediates generated by this migration have been trapped either by a Heck reaction employing ethyl acrylate or by Suzuki cross-coupling using arylboronic acids. This palladium migration can be activated or deactivated by choosing the appropriate reaction conditions. Chemical and computational evidence supports the presence of an equilibrium that correlates with the C-H acidity of the available arene positions.

  DOI：

  10.1021/ja069238z