N¹-(4-oxo-2,5-cyclohexadien-1-ylidene)-N²-benzyl-2,2,2-trifluoroethanimidamide | 155447-70-4

• 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: N¹-(4-oxo-2,5-cyclohexadien-1-ylidene)-N²-benzyl-2,2,2-trifluoroethanimidamide
• 英文别名: N'-benzyl-2,2,2-trifluoro-N-(4-oxocyclohexa-2,5-dien-1-ylidene)ethanimidamide
• CAS: 155447-70-4
• 化学式: C₁₅H₁₁F₃N₂O
• 分子量: 292.26
• InChiKey: RYWIPPLKQJRWRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  41.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N¹-(4-oxo-2,5-cyclohexadien-1-ylidene)-N²-benzyl-2,2,2-trifluoroethanimidamide 在 三氟化硼乙醚 作用下， 以 苯 为溶剂， 反应 1.0h， 以60%的产率得到1-benzyl-2-(trifluoromethyl)-6-hydroxybenzimidazole
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00125a028
• 作为产物：
  描述：

  2,2,2-三氟-N-(4-甲氧基苯基)-亚氨基氯化物 在 水 作用下， 以 乙腈 、 苯 为溶剂， 生成 N¹-(4-oxo-2,5-cyclohexadien-1-ylidene)-N²-benzyl-2,2,2-trifluoroethanimidamide
  参考文献：
  名称：

  Electrochemical Oxidation of N,N'-Disubstituted Trifluoroethanimidamides. An Approach to N-Substituted 2-(Trifluoromethyl)benzimidazoles

  摘要：

  Electrochemical oxidation of N,N'-disubstituted trifluoroethanimidamides 11 in dry acetonitrile and in aqueous acetonitrile provided N-substituted 2-(trifluoromethyl)benzimidazoles 15 and N-1-(4-oxo-2,5-cyclohexadien-1-ylidene)-N-2-substituted-2,2,2-trifluoroethanimidamides (p-benzoquinone imine derivatives) 20, respectively. In dry acetonitrile, electron-donating para substituents in the N,N'-diaryl derivatives strongly promoted the formation of benzimidazoles, whereas N-alkyl-N'(4-methoxyphenyl) derivatives provided rather complex mixtures of 11,20, and polymeric compounds. In wet acetonitrile, p-benzoquinone imines 20 were major products regardless of the substituents. An ECEC process via two-electron oxidation is proposed.

  DOI：

  10.1021/jo00090a017

文献信息

• Electrochemical Oxidation of N,N'-Disubstituted Trifluoroethanimidamides. An Approach to N-Substituted 2-(Trifluoromethyl)benzimidazoles
  作者：Kenji Uneyama、Masafumi Kobayashi

  DOI：10.1021/jo00090a017

  日期：1994.6

  Electrochemical oxidation of N,N'-disubstituted trifluoroethanimidamides 11 in dry acetonitrile and in aqueous acetonitrile provided N-substituted 2-(trifluoromethyl)benzimidazoles 15 and N-1-(4-oxo-2,5-cyclohexadien-1-ylidene)-N-2-substituted-2,2,2-trifluoroethanimidamides (p-benzoquinone imine derivatives) 20, respectively. In dry acetonitrile, electron-donating para substituents in the N,N'-diaryl derivatives strongly promoted the formation of benzimidazoles, whereas N-alkyl-N'(4-methoxyphenyl) derivatives provided rather complex mixtures of 11,20, and polymeric compounds. In wet acetonitrile, p-benzoquinone imines 20 were major products regardless of the substituents. An ECEC process via two-electron oxidation is proposed.
• 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.