N-(4-bromophenyl)-2-methyl-1H-indole-3-carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-bromophenyl)-2-methyl-1H-indole-3-carboxamide
• 化学式: C₁₆H₁₃BrN₂O
• 分子量: 329.196
• InChiKey: OZOGYEIEYWSJMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-(4-bromophenyl)-N-(buta-2,3-dien-1-yl)hydroxylamine 、 亚硝基苯 在 chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) 、 氧气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 以77%的产率得到N-(4-bromophenyl)-2-methyl-1H-indole-3-carboxamide
  参考文献：
  名称：

  [3 + 2]-Annulations of N-Hydroxy Allenylamines with Nitrosoarenes: One-Pot Synthesis of Substituted Indole Products

  摘要：

  In the presence of O-2 and an IPrCuCl additive (5 mol %), [3 + 2]-annulation reactions of N-hydroxyaniline with nitrosobenzenes in cold toluene form isoxazolidin-5-ol derivatives. Heating the same reaction mixture with DBU in toluene affords highly functionalized indole products efficiently. This method provides short synthesis of several bioactive molecules including WIN 48098, WIN 53365, and JWH 015.

  DOI：

  10.1021/acs.orglett.5b03447

文献信息

• [3 + 2]-Annulations of <i>N</i>-Hydroxy Allenylamines with Nitrosoarenes: One-Pot Synthesis of Substituted Indole Products
  作者：Pankaj Sharma、Rai-Shung Liu

  DOI：10.1021/acs.orglett.5b03447

  日期：2016.2.5

  In the presence of O-2 and an IPrCuCl additive (5 mol %), [3 + 2]-annulation reactions of N-hydroxyaniline with nitrosobenzenes in cold toluene form isoxazolidin-5-ol derivatives. Heating the same reaction mixture with DBU in toluene affords highly functionalized indole products efficiently. This method provides short synthesis of several bioactive molecules including WIN 48098, WIN 53365, and JWH 015.