(2-bromophenyl)-(R)-2-methoxy-1-phenylethylamine | 361979-02-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2-bromophenyl)-(R)-2-methoxy-1-phenylethylamine
• 英文别名: 2-bromo-N-[(1R)-2-methoxy-1-phenylethyl]aniline
• CAS: 361979-02-4
• 化学式: C₁₅H₁₆BrNO
• 分子量: 306.202
• InChiKey: FMBLFIZFZYUAQW-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-bromophenyl)-(R)-2-methoxy-1-phenylethylamine 在 tris(dibenzylideneacetone)dipalladium (0) 、 盐酸羟胺 、 sodium acetate 、 对甲苯磺酸 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 9.04h， 生成 1-[(R)-2-methoxy-1-phenylethyl]-1H-benzimidazole
  参考文献：
  名称：

  Aromatic Amination/Imination Approach to Chiral Benzimidazoles

  摘要：

  The powerful Buchwald-Hartwig amination was utilized for the construction of the benzimidazole nucleus with the substituted nitrogen atom bearing a chiral substituent. A successive amination/imination was followed by an acid-catalyzed ring closure step to give the benzimidazole ring. The products were deprotonated and acylated at the C2 position and could be alkylated on nitrogen to give chiral benzimidazolium salts.

  DOI：

  10.1021/jo016251n
• 作为产物：
  描述：

  (R)-(-)-2-甲氧基-1-苯乙胺 、 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 48.0h， 以98%的产率得到(2-bromophenyl)-(R)-2-methoxy-1-phenylethylamine
  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.
• Aromatic Amination/Imination Approach to Chiral Benzimidazoles
  作者：Felix M. Rivas、Anthony J. Giessert、Steven T. Diver

  DOI：10.1021/jo016251n

  日期：2002.3.1

  The powerful Buchwald-Hartwig amination was utilized for the construction of the benzimidazole nucleus with the substituted nitrogen atom bearing a chiral substituent. A successive amination/imination was followed by an acid-catalyzed ring closure step to give the benzimidazole ring. The products were deprotonated and acylated at the C2 position and could be alkylated on nitrogen to give chiral benzimidazolium salts.