4-(2-methyl-2-phenylhydrazono)butanenitrile | 91331-67-8

• 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: 4-(2-methyl-2-phenylhydrazono)butanenitrile
• 英文别名: 4-[Methyl(phenyl)hydrazinylidene]butanenitrile
• CAS: 91331-67-8
• 化学式: C₁₁H₁₃N₃
• 分子量: 187.244
• InChiKey: ZALLXHQADKOOGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氨基丁腈 、 1-甲基-1-苯肼 在 2-丁烯腈 、 palladium 10% on activated carbon 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以78%的产率得到4-(2-methyl-2-phenylhydrazono)butanenitrile
  参考文献：
  名称：

  钯催化的胺类脱氢生成胺。通过胺与芳肼的交叉偶联反应获得吲哚的自然路线

  摘要：

  AbstractH‐substituted imines are elusive compounds formed when aldehydes or ketones are mixed with ammonia. However, this class of molecules can be prepared through selective removal of a hydrogen molecule from a primary amine using a transition metal catalyst. This biomimetic transformation, previously employed for the N‐alkylation of anilines, is applied here to a domino preparation of differently substituted indoles from aliphatic primary amines and arylhydrazines. Several different linear and branched aliphatic primary amines are oxidized with reusable palladium on charcoal to the corresponding primary imines entrapped as arylhydrazones that can be isolated as such. Arylhydrazones can be further converted into N‐alkylindole derivatives via an acid‐mediated indolisation reaction. The one‐pot domino hydrogen transfer Fischer indole synthesis under heterogeneous catalysis is also possible, giving access to diverse substituted indoles, including NH indoles obtained after deprotection of the corresponding benzyl compounds. The truly heterogeneous nature of the catalyst was demonstrated by recycling the catalyst in the same reaction, and in other palladium‐catalysed transformations.magnified image

  DOI：

  10.1002/adsc.201300559