N-acetoxy-2-(acetoxymethyl)benzimidazole | 449796-13-8

• 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: N-acetoxy-2-(acetoxymethyl)benzimidazole
• 英文别名: 2-acetoxymethyl-1-acetyl-1H-benzimidazole；2-Acetoxymethyl-1-acetyl-1H-benzimidazol；(1-acetylbenzimidazol-2-yl)methyl acetate
• CAS: 449796-13-8
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: UFOYCOSYYNCZGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.19
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-acetoxy-2-(acetoxymethyl)benzimidazole 在 sodium hydroxide 、 苄基三乙基氯化铵 、 水 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.5h， 生成 (1-甲基-1H-苯并咪唑-2-基)甲醇
  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
• 作为产物：
  描述：

  2-羟甲基苯并咪唑 、 乙酸酐 反应 2.0h， 生成 N-acetoxy-2-(acetoxymethyl)benzimidazole
  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

• Sacharowa et al., Zhurnal Obshchei Khimii, 1953, vol. 23, p. 1225,1229; engl. Ausg. S. 1289, 1292
  作者：Sacharowa et al.

  DOI：——

  日期：——