1-(1-甲基-1H-苯并[d]咪唑-2-基)乙酸乙酯 | 944061-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1-(1-甲基-1H-苯并[d]咪唑-2-基)乙酸乙酯
• 英文名称: 1-(1-methyl-1H-benzo[d]imidazol-2-yl)ethyl acetate
• CAS: 944061-74-9
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: YZFSKKMYBJROND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(1-甲基-1H-苯并[d]咪唑-2-基)乙酸乙酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以80%的产率得到(9ci)-alpha,1-二甲基-1H-苯并咪唑-2-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-(1-羟乙基)苯并咪唑 在 苄基三乙基氯化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 1-(1-甲基-1H-苯并[d]咪唑-2-基)乙酸乙酯
  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