1-Benzyl-(2-α-hydroxybenzyl)-benzimidazol | 147-64-8

• 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-Benzyl-(2-α-hydroxybenzyl)-benzimidazol
• 英文别名: (1-benzyl-1H-benzoimidazol-2-yl)-phenyl-methanol；(1-Benzylbenzimidazol-2-yl)-phenylmethanol
• CAS: 147-64-8
• 化学式: C₂₁H₁₈N₂O
• 分子量: 314.387
• InChiKey: MHAZCQNKLXWHEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(羟基苯基甲基)苯并咪唑 在 sodium hydroxide 、 苄基三乙基氯化铵 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.5h， 生成 1-Benzyl-(2-α-hydroxybenzyl)-benzimidazol
  参考文献：
  名称：

  Alternate Method for the Synthesis of N‐Alkyl/aralkyl‐2‐(α‐hydroxy Alkyl/aralkyl)benzimidazoles via Regiospecific Acetylation

  摘要：

  Acetylation of 1H-2-(alpha-hydroxyalkyl/aryl) benzimidazoles 2 with Ac2O results in the regiospecific formation of O-acetoxy derivative 3, which on alkylation with alkylating agents in nonaqueous media under phase-transfer catalytic conditions affords N-alkyl derivatives 4. The latter, on hydrolysis in an aqueous basic medium, results in the title compounds 5 in good yields in high purity. Alternatively, 5 can also be obtained by reduction of 1-substituted-2-acetyl/benzoylbenzimidazoles 8 using NaBH4.

  DOI：

  10.1080/00397910701265556

文献信息

• Alternate Method for the Synthesis of N‐Alkyl/aralkyl‐2‐(α‐hydroxy Alkyl/aralkyl)benzimidazoles via Regiospecific Acetylation
  作者：P. K. Dubey、P.V.V. Prasada Reddy、K. Srinivas

  DOI：10.1080/00397910701265556

  日期：2007.5.1

  Acetylation of 1H-2-(alpha-hydroxyalkyl/aryl) benzimidazoles 2 with Ac2O results in the regiospecific formation of O-acetoxy derivative 3, which on alkylation with alkylating agents in nonaqueous media under phase-transfer catalytic conditions affords N-alkyl derivatives 4. The latter, on hydrolysis in an aqueous basic medium, results in the title compounds 5 in good yields in high purity. Alternatively, 5 can also be obtained by reduction of 1-substituted-2-acetyl/benzoylbenzimidazoles 8 using NaBH4.