1-phenyl-2-(2,2,2-trifluoroethyl)-1H-benzimidazole | 1058164-72-9

• 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-phenyl-2-(2,2,2-trifluoroethyl)-1H-benzimidazole
• 英文别名: 1-Phenyl-2-(2,2,2-trifluoroethyl)benzimidazole；1-phenyl-2-(2,2,2-trifluoroethyl)benzimidazole
• CAS: 1058164-72-9
• 化学式: C₁₅H₁₁F₃N₂
• 分子量: 276.261
• InChiKey: IYDZLECZZJCNCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-(2,2,2-trifluoroethyl)-1H-benzimidazole 以 sodium hydroxide 为溶剂， 生成 2-(1-Phenylbenzimidazol-2-yl)acetic acid 、 2-甲基-1-苯基-1H-苯并咪唑
  参考文献：
  名称：

  POCl3-mediated synthesis of hydrolysis-prone 2-trifluoroethylbenzimidazoles

  摘要：

  Loss of a trifluoromethyl group has been observed as an unproductive side reaction in the formation of 2-trifluoroethylbenzimidazoles. A hydrolytic mechanism for this transformation is proposed that is consistent with evidence for the identity of reaction intermediates. Cyclodehydration with POCl3 suppresses hydrolysis of the trifluoromethyl group and provides 2-trifluoroethylbenzimidazoles in good yields. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.069
• 作为产物：
  描述：

  N-(2-anilinophenyl)-3,3,3-trifluoropropanamide 在 三氯氧磷 作用下， 反应 3.5h， 以97%的产率得到1-phenyl-2-(2,2,2-trifluoroethyl)-1H-benzimidazole
  参考文献：
  名称：

  POCl3-mediated synthesis of hydrolysis-prone 2-trifluoroethylbenzimidazoles

  摘要：

  Loss of a trifluoromethyl group has been observed as an unproductive side reaction in the formation of 2-trifluoroethylbenzimidazoles. A hydrolytic mechanism for this transformation is proposed that is consistent with evidence for the identity of reaction intermediates. Cyclodehydration with POCl3 suppresses hydrolysis of the trifluoromethyl group and provides 2-trifluoroethylbenzimidazoles in good yields. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.069

文献信息

• POCl3-mediated synthesis of hydrolysis-prone 2-trifluoroethylbenzimidazoles
  作者：Kausik K. Nanda、B. Wesley Trotter

  DOI：10.1016/j.tetlet.2008.06.069

  日期：2008.9

  Loss of a trifluoromethyl group has been observed as an unproductive side reaction in the formation of 2-trifluoroethylbenzimidazoles. A hydrolytic mechanism for this transformation is proposed that is consistent with evidence for the identity of reaction intermediates. Cyclodehydration with POCl3 suppresses hydrolysis of the trifluoromethyl group and provides 2-trifluoroethylbenzimidazoles in good yields. (C) 2008 Elsevier Ltd. All rights reserved.