N,N'-dibenzyl-1,1'-binaphthalen-4,4'-diamine | 1331748-56-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N'-dibenzyl-1,1'-binaphthalen-4,4'-diamine
• 英文别名: N,N'-dibenzyl-(1,1'-binaphthyl)-4,4'-diamine；N-benzyl-4-[4-(benzylamino)naphthalen-1-yl]naphthalen-1-amine
• CAS: 1331748-56-1
• 化学式: C₃₄H₂₈N₂
• 分子量: 464.61
• InChiKey: NDLFTSWYXNRNIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-苄基-1-萘胺 在 potassium carbonate 、 iron(III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.08h， 以75%的产率得到N,N'-dibenzyl-1,1'-binaphthalen-4,4'-diamine
  参考文献：
  名称：

  Iron(III)-Promoted Oxidative Coupling of Naphthylamines: Synthetic and Mechanistic Investigations

  摘要：

  A facile route to the synthesis of 1,1'-binaphthyl-4,4'-diamines (naphthidines) and 1,1'-binaphthyl-2,2'-diamines (BINAMs) was developed by the oxidative homocoupling of 1- and 2-naphthylamines, respectively, using FeCl(3) as oxidant and K(2)CO(3) as base in 1,2-dichloroethane under ambient conditions. A preliminary mechanistic investigation was performed by the ESR spectroscopy and intermediate-trapping technique.

  DOI：

  10.1021/ol202058r

文献信息

• Aerobic Oxidative Homocoupling of Aryl Amines Using Heterogeneous Rhodium Catalysts
  作者：Kenji Matsumoto、Kento Dougomori、Shohei Tachikawa、Takanori Ishii、Mitsuru Shindo

  DOI：10.1021/ol502197p

  日期：2014.9.19

  The first heterogeneous catalyzed oxidative coupling of aryl amines is reported. Aryl amines were dimerized at room temperature under air using a heterogeneous Rh/C catalyst in the presence of acids. By choosing a suitable acidic solvent, biaryl compounds and carbazoles were selectively prepared in good yields. This reaction is operationally simple and provides an efficient synthetic methodology for the preparation of biaryl diamines via oxidative C-H activation.