N-phenyl-N'-(R)-2-methoxy-1-phenyl-ethyl-1,2-diaminobenzene | 361979-04-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-phenyl-N'-(R)-2-methoxy-1-phenyl-ethyl-1,2-diaminobenzene
• 英文别名: 2-N-[(1R)-2-methoxy-1-phenylethyl]-1-N-phenylbenzene-1,2-diamine
• CAS: 361979-04-6
• 化学式: C₂₁H₂₂N₂O
• 分子量: 318.418
• InChiKey: SQHKHCRMJBCTAO-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  33.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  原甲酸三乙酯 、 N-phenyl-N'-(R)-2-methoxy-1-phenyl-ethyl-1,2-diaminobenzene 在 盐酸 作用下， 以91%的产率得到1-(R)-2-methoxy-1-(phenyl-ethyl)-3-phenyl-benzimidazolium chloride
  参考文献：
  名称：

  A Versatile Synthesis of Substituted Benzimidazolium Salts by an Amination/Ring Closure Sequence

  摘要：

  [GRAPHICS]A new method to produce benzimidazolium salts based on a successive Buchwald-Hartwig amination and ring closure is reported. A variety of different benzimidazolium salts can be prepared using this procedure. Amines that bear an alpha -chiral group undergo the reaction to furnish chiral benzimidazolium salts. The salts that lack a C2 substituent on the heterocycle are readily deprotonated to give nucleophilic carbenes.

  DOI：

  10.1021/ol016254m
• 作为产物：
  描述：

  1,2-二溴苯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 69.0h， 生成 N-phenyl-N'-(R)-2-methoxy-1-phenyl-ethyl-1,2-diaminobenzene
  参考文献：
  名称：

  A Versatile Synthesis of Substituted Benzimidazolium Salts by an Amination/Ring Closure Sequence

  摘要：

  [GRAPHICS]A new method to produce benzimidazolium salts based on a successive Buchwald-Hartwig amination and ring closure is reported. A variety of different benzimidazolium salts can be prepared using this procedure. Amines that bear an alpha -chiral group undergo the reaction to furnish chiral benzimidazolium salts. The salts that lack a C2 substituent on the heterocycle are readily deprotonated to give nucleophilic carbenes.

  DOI：

  10.1021/ol016254m

文献信息

• A Versatile Synthesis of Substituted Benzimidazolium Salts by an Amination/Ring Closure Sequence
  作者：Felix M. Rivas、Uzma Riaz、Anthony Giessert、Jason A. Smulik、Steven T. Diver

  DOI：10.1021/ol016254m

  日期：2001.8.1

  [GRAPHICS]A new method to produce benzimidazolium salts based on a successive Buchwald-Hartwig amination and ring closure is reported. A variety of different benzimidazolium salts can be prepared using this procedure. Amines that bear an alpha -chiral group undergo the reaction to furnish chiral benzimidazolium salts. The salts that lack a C2 substituent on the heterocycle are readily deprotonated to give nucleophilic carbenes.