1-(4'-methylphenyl)-2-(trifluoromethyl)-6-hydroxybenzimidazole | 137927-36-7

• 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-(4'-methylphenyl)-2-(trifluoromethyl)-6-hydroxybenzimidazole
• 英文别名: 3-(p-tolyl)-2-(trifluoromethyl)-3H-benzoimidazol-5-ol；3-(4-methylphenyl)-2-(trifluoromethyl)benzimidazol-5-ol
• CAS: 137927-36-7
• 化学式: C₁₅H₁₁F₃N₂O
• 分子量: 292.26
• InChiKey: TWZCXKDXDSCZCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N¹-(4-oxo-2,5-cyclohexadien-1-ylidene)-N²-(4-methylphenyl)-2,2,2-trifluoroethanimidamide 在 三氟化硼乙醚 作用下， 以 苯 为溶剂， 以100%的产率得到1-(4'-methylphenyl)-2-(trifluoromethyl)-6-hydroxybenzimidazole
  参考文献：
  名称：

  Syntheses of 1-aryl-2-trifluoromethylbenzimidazoles via electrochemically prepared p-benzoquinone imines

  摘要：

  Electrooxidation of N-(4-methoxyphenyl)-N'-aryl-2,2,2-trifluoroethanimidamides 1 in an MeCN-H2O-NaClO4-(C)-(Pt) system affords p-benzoquinone imines 2 which are converted to 1-aryl-2-trifluoromethylbenzimidazoles 3 by acid catalyzed cyclization.

  DOI：

  10.1016/s0040-4039(00)79443-3

文献信息

• Syntheses of 1-aryl-2-trifluoromethylbenzimidazoles via electrochemically prepared p-benzoquinone imines
  作者：Kenji Uneyama、Masafumi Kobayashi

  DOI：10.1016/s0040-4039(00)79443-3

  日期：1991.10

  Electrooxidation of N-(4-methoxyphenyl)-N'-aryl-2,2,2-trifluoroethanimidamides 1 in an MeCN-H2O-NaClO4-(C)-(Pt) system affords p-benzoquinone imines 2 which are converted to 1-aryl-2-trifluoromethylbenzimidazoles 3 by acid catalyzed cyclization.
• Intramolecular Cyclization of N1-(4-Oxo-2,5-cyclohexadien-1-ylidene)-N2-substituted-2,2,2- trifluoroethanimidamides (p-Benzoquinone Imine Derivatives): Syntheses of Trifluoromethylated 6-Hydroxybenzimidazoles and Spiro Dienone Diazacarbocycles
  作者：Masafumi Kobayashi、Kenji Uneyama、Noritaka Hamada、Setsuo Kashino

  DOI：10.1021/jo00125a028

  日期：1995.10

  Lewis acid-catalyzed intramolecular cyclization of N-1-(4-oxo-2,5-cyclohexadien-1-ylidene)-N-2- substituted-2,2,2-trifluoroethanimidamide (p-benzoquinone imine derivatives, 1) prepared by electrooxidation of N-(4-methoxyphenyli-N'-substituted-2,2 2-trifluoroethanimidamides 2 occurred to give 1-substituted-2-(trifluoromethyl)-6-hydroxybenzimidazoles 3. Alternatively, thermal cyclization of 1 gave spiro dienone diazacarbocycles 9 and 10, which were converted into diazepine 12 via a dienone-phenol rearrangement.