N-(3-bromo-1-methylindol-2-yl)-1,1-diphenylmethanimine | 1392400-86-0

• 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-(3-bromo-1-methylindol-2-yl)-1,1-diphenylmethanimine
• CAS: 1392400-86-0
• 化学式: C₂₂H₁₇BrN₂
• 分子量: 389.294
• InChiKey: IRIUIBOBFFTBLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-甲基吲哚 、 benzophenone O-acetyl oxime 在 copper(I) bromide dimethylsulfide complex 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以55%的产率得到N-(3-bromo-1-methylindol-2-yl)-1,1-diphenylmethanimine
  参考文献：
  名称：

  Copper-Mediated Multiple C–H Functionalization of AromaticN-Heterocycles: Bromoamination of Indoles and Pyrroles

  摘要：

  A copper-mediated bromoamination of aromatic N-heterocycles has been achieved using oxime esters as the N-reagents under mild conditions (ca. 70 degrees C). The reaction with N-alkyl indoles proceeds regioselectively to produce the 2-amino-3-bromo indole derivatives as confirmed by X-ray crystallographic analysis of the brominated product, 3aa-Br. With N-methylpyrrole both the monobromoaminated and dibromoaminated products were produced by this method.

  DOI：

  10.1021/om300553b

文献信息

• Copper-Mediated Multiple C–H Functionalization of Aromatic<i>N</i>-Heterocycles: Bromoamination of Indoles and Pyrroles
  作者：Alex John、Kenneth M. Nicholas

  DOI：10.1021/om300553b

  日期：2012.11.26

  A copper-mediated bromoamination of aromatic N-heterocycles has been achieved using oxime esters as the N-reagents under mild conditions (ca. 70 degrees C). The reaction with N-alkyl indoles proceeds regioselectively to produce the 2-amino-3-bromo indole derivatives as confirmed by X-ray crystallographic analysis of the brominated product, 3aa-Br. With N-methylpyrrole both the monobromoaminated and dibromoaminated products were produced by this method.