(1-[(S)-1-phenylethyl]-1H-benzimidazol-2-yl)-phenyl-methanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1-[(S)-1-phenylethyl]-1H-benzimidazol-2-yl)-phenyl-methanone
• 英文别名: phenyl-[1-[(1S)-1-phenylethyl]benzimidazol-2-yl]methanone
• 化学式: C₂₂H₁₈N₂O
• 分子量: 326.398
• InChiKey: WJLBHLRSZLJCOW-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (aS)-N-(2-溴苯基)-alpha-甲基-苯甲胺 在 正丁基锂 、 tris(dibenzylideneacetone)dipalladium (0) 、 盐酸羟胺 、 sodium acetate 、 对甲苯磺酸 、 sodium t-butanolate 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 为溶剂， 反应 9.92h， 生成 (1-[(S)-1-phenylethyl]-1H-benzimidazol-2-yl)-phenyl-methanone
  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

文献信息

• 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.