2-(Acetoxy-phenyl-methyl)-benzimidazol | 22841-76-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(Acetoxy-phenyl-methyl)-benzimidazol
• 英文别名: acetoxy-(1H-benzoimidazol-2-yl)-phenyl-methane；1H-benzimidazol-2-yl(phenyl)methyl acetate；[1H-benzimidazol-2-yl(phenyl)methyl] acetate
• CAS: 22841-76-5
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: KBGMBRJZDUKEIM-UHFFFAOYSA-N

物化性质

• 熔点：
  170-172 °C(Solv: benzene (71-43-2))
• 沸点：
  495.3±38.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(Acetoxy-phenyl-methyl)-benzimidazol 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 0.5h， 生成 1-Ethyl-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
• 作为产物：
  描述：

  2-(羟基苯基甲基)苯并咪唑 、 乙酸酐 反应 2.0h， 以80%的产率得到2-(Acetoxy-phenyl-methyl)-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.