(Z)-methyl 3-(4-bromophenyl)-2-(3-methyl-1H-indole-1-carbonyl)acrylate | 1338700-71-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-methyl 3-(4-bromophenyl)-2-(3-methyl-1H-indole-1-carbonyl)acrylate
• 英文别名: methyl (Z)-3-(4-bromophenyl)-2-(3-methylindole-1-carbonyl)prop-2-enoate
• CAS: 1338700-71-2
• 化学式: C₂₀H₁₆BrNO₃
• 分子量: 398.256
• InChiKey: UTWRVTWWOXBAIV-BOPFTXTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 3-(4-bromophenyl)-2-(3-methyl-1H-indole-1-carbonyl)acrylate 在 indium(III) triflate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 14.0h， 生成 methyl 1-(4-bromophenyl)-9-methyl-3-oxo-2,3-dihydro-1H-pyrrolo[1,2-a]indole-2-carboxylate 、 methyl 1-(4-bromophenyl)-9-methyl-3-oxo-2,3-dihydro-1H-pyrrolo[1,2-a]indole-2-carboxylate
  参考文献：
  名称：

  Diastereoselective Intramolecular Friedel–Crafts Cyclizations of Substituted Methyl 2-(1H-indole-1-carbonyl)acrylates: Efficient Access to Functionalized 1H-Pyrrolo[1,2-a]indoles

  摘要：

  A general, catalytic method for the diastereoselective synthesis of functionalized 1H-pyrrolo[1,2-a]indoles via an intramolecular Friedel-Crafts alkylation of N-acyl indoles Is reported. Products were obtained In excellent yields (up to 98%) with high diastereoselectivities (up to >25:1 dr).

  DOI：

  10.1021/ol202431x
• 作为产物：
  描述：

  3-甲基吲哚 在 哌啶 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 12.0h， 生成 (Z)-methyl 3-(4-bromophenyl)-2-(3-methyl-1H-indole-1-carbonyl)acrylate
  参考文献：
  名称：

  Diastereoselective Intramolecular Friedel–Crafts Cyclizations of Substituted Methyl 2-(1H-indole-1-carbonyl)acrylates: Efficient Access to Functionalized 1H-Pyrrolo[1,2-a]indoles

  摘要：

  A general, catalytic method for the diastereoselective synthesis of functionalized 1H-pyrrolo[1,2-a]indoles via an intramolecular Friedel-Crafts alkylation of N-acyl indoles Is reported. Products were obtained In excellent yields (up to 98%) with high diastereoselectivities (up to >25:1 dr).

  DOI：

  10.1021/ol202431x

文献信息

• Diastereoselective Intramolecular Friedel–Crafts Cyclizations of Substituted Methyl 2-(1<i>H</i>-indole-1-carbonyl)acrylates: Efficient Access to Functionalized 1<i>H</i>-Pyrrolo[1,2-<i>a</i>]indoles
  作者：Dadasaheb V. Patil、Marchello A. Cavitt、Stefan France

  DOI：10.1021/ol202431x

  日期：2011.11.4

  A general, catalytic method for the diastereoselective synthesis of functionalized 1H-pyrrolo[1,2-a]indoles via an intramolecular Friedel-Crafts alkylation of N-acyl indoles Is reported. Products were obtained In excellent yields (up to 98%) with high diastereoselectivities (up to >25:1 dr).