2-benzyl-1-methyl-1H-indole-3-carbonitrile | 938326-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-benzyl-1-methyl-1H-indole-3-carbonitrile
• 英文别名: 2-Benzyl-1-methylindole-3-carbonitrile
• CAS: 938326-96-6
• 化学式: C₁₇H₁₄N₂
• 分子量: 246.312
• InChiKey: LPFRTYWGAXCPQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-氰基-2-甲基吲哚 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium hydride 、 cesium fluoride 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 乙二醇二甲醚 、 mineral oil 为溶剂， 反应 1.75h， 生成 2-benzyl-1-methyl-1H-indole-3-carbonitrile
  参考文献：
  名称：

  Copper-Catalyzed Benzylic C−H Oxygenation under an Oxygen Atmosphere via N-H Imines as an Intramolecular Directing Group

  摘要：

  Copper-catalyzed benzylic C-H oxygenation under an oxygen atmosphere was developed starting from carbonitriles and Grignard reagents via N-H imine intermediates. The present process is characterized by the following two-step sequence in a one-pot manner: (1) addition of Grignard reagents to carbonitriles to form N-H imines and (2) benzylic C-H oxygenation (C=O bond formation) triggered by 1,5-hydrogen atom transfer with transient iminyl copper species.

  DOI：

  10.1021/ol200425c

文献信息

• Copper-Catalyzed Benzylic C−H Oxygenation under an Oxygen Atmosphere via <i>N</i>-H Imines as an Intramolecular Directing Group
  作者：Line Zhang、Gim Yean Ang、Shunsuke Chiba

  DOI：10.1021/ol200425c

  日期：2011.4.1

  Copper-catalyzed benzylic C-H oxygenation under an oxygen atmosphere was developed starting from carbonitriles and Grignard reagents via N-H imine intermediates. The present process is characterized by the following two-step sequence in a one-pot manner: (1) addition of Grignard reagents to carbonitriles to form N-H imines and (2) benzylic C-H oxygenation (C=O bond formation) triggered by 1,5-hydrogen atom transfer with transient iminyl copper species.