1-[(S)-1-cyclohexylethyl]-1H-benzimidazole | 407618-37-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-[(S)-1-cyclohexylethyl]-1H-benzimidazole
• 英文别名: 1-[(1S)-1-cyclohexylethyl]benzimidazole
• CAS: 407618-37-5
• 化学式: C₁₅H₂₀N₂
• 分子量: 228.337
• InChiKey: LSRSPISEZZUXCR-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[(S)-1-cyclohexylethyl]-1H-benzimidazole 在 silver tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 1-[(S)-1-phenylethyl]-3-butyl-1H-benzimidazolium tetrafluoroborate
  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：

  N-[(S)-1-cyclohexylethyl]-N'-(diphenylmethylene)-1,2-benzenediamine 在 盐酸羟胺 、 sodium acetate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 1-[(S)-1-cyclohexylethyl]-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