4,4'-Dicyano-4"-methyl-triphenylamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4,4'-Dicyano-4"-methyl-triphenylamine
• 英文别名: 4-(N-(4-cyanophenyl)-4-methylanilino)benzonitrile
• 化学式: C₂₁H₁₅N₃
• 分子量: 309.37
• InChiKey: PGRQPCCHVJMSED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氯苯甲腈 、 乙烷,三氯氟- 在 tris-(dibenzylideneacetone)dipalladium(0) 、 2-(二叔丁基膦)联苯 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以81%的产率得到4-(p-tolylamino)benzonitrile
  参考文献：
  名称：

  Simple, Efficient Catalyst System for the Palladium-Catalyzed Amination of Aryl Chlorides, Bromides, and Triflates

  摘要：

  Palladium complexes supported by (o-biphenyl)P(t-Bu)(2) (3) or (o-biphenyl)PCy2 (4) are efficient catalysts for the catalytic amination of a wide variety of aryl halides and triflates. Use of ligand 3 allows for the room-temperature catalytic amination of many aryl chloride, bromide, and triflate substrates, while ligand 4 is effective for the amination of functionalized substrates or reactions of acyclic secondary amines. The catalysts perform well for a large number of different substrate combinations at 80-110 degrees C, including chloropyridines and functionalized aryl halides and triflates using 0.5-1.0 mol % Pd; some reactions proceed efficiently at low catalyst levels (0.05 mol % Pd). These ligands are effective for almost all substrate combinations that have been previously reported with various other ligands, and they represent the most generally effective catalyst system reported to date. Ligands 3 and 4 are air-stable, crystalline solids that are commercially available. Their effectiveness is believed to be due to a combination of steric and electronic properties that promote oxidative addition, Pd-N bond formation, and reductive elimination.

  DOI：

  10.1021/jo991699y

文献信息

• US5536866A
  申请人：——

  公开号：US5536866A

  公开（公告）日：1996-07-16
• US5633337A
  申请人：——

  公开号：US5633337A

  公开（公告）日：1997-05-27