N-benzyl-2-(α-hydroxyethyl)benzimidazole | 56653-47-5

• 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: N-benzyl-2-(α-hydroxyethyl)benzimidazole
• 英文别名: 1-(1-benzyl-1H-benzo[d]imidazol-2-yl)ethanol；1-(1-benzyl-1H-benzoimidazol-2-yl)-ethanol；1-Benzyl-2-(α-hydroxyaethyl)benzimidazol；1-(1-benzyl-1H-benzimidazol-2-yl)ethanol；1-(1-benzylbenzimidazol-2-yl)ethanol
• CAS: 56653-47-5
• 化学式: C₁₆H₁₆N₂O
• mdl: MFCD01056115
• 分子量: 252.316
• InChiKey: LKEHINZOIKHAIM-UHFFFAOYSA-N

物化性质

• 熔点：
  124-126 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  459.8±38.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)
• 溶解度：
  35.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-(α-hydroxyethyl)benzimidazole 在 溶剂黄146 、 bis(2-methyl-1H-benzimidazolinium) dichromate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以83%的产率得到1-(1-苄基苯并咪唑-2-基)乙酮
  参考文献：
  名称：

  Ramaiah; Dubey; Ramanatham, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 7, p. 1765 - 1767

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(1-acetoxy-ethyl)-1H-benzimidazole 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 N-benzyl-2-(α-hydroxyethyl)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

• Ramaiah; Dubey; Ramanatham, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 7, p. 1765 - 1767
  作者：Ramaiah、Dubey、Ramanatham、Kumar, C. Ravi、Grossert

  DOI：——

  日期：——
• Investigations of unsaturated azoles. 13. Synthesis and some reactions of 1-alkylbenzimidazoles
  作者：I. I. Popov

  DOI：10.1007/bf01164866

  日期：1996.6
• Lipase mediated kinetic resolution of benzimidazolyl ethanols
  作者：Ravi Kumar Cheedrala、Rachna Sachwani、Palakodety Radha Krishna

  DOI：10.1016/j.tetasy.2008.03.021

  日期：2008.5

  Enantioselective trans-acylation of the racemic benzimidazolyl ethanols was achieved via enzymatic kinetic resolution. A range of commercially available lipases were screened and Novozyme-435 was established as the optimal catalyst. N-Protection was found to be mandatory for effective transesterification. However, electron-withdrawing substituents reduced the enantioselectivity to some extent when compared to the other substituents. (C) 2008 Published by Elsevier Ltd.
• 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.
• Dubey; Kumar, C. Ravi; Babu, Balaji, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 12, p. 3128 - 3130
  作者：Dubey、Kumar, C. Ravi、Babu, Balaji

  DOI：——

  日期：——