2,2,2-trifluoro-N-4-methoxyphenyll-N'-4-methoxyphenyl-acetamidine | 137927-24-3

• 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: 2,2,2-trifluoro-N-4-methoxyphenyll-N'-4-methoxyphenyl-acetamidine
• 英文别名: N,N'-bis(4-methoxyphenyl)-2,2,2-trifluoroethanimidamide；2,2,2-trifluoro-N,N'-bis(4-methoxyphenyl)ethanimidamide
• CAS: 137927-24-3
• 化学式: C₁₆H₁₅F₃N₂O₂
• 分子量: 324.303
• InChiKey: SQFSAFLJBGXAJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  42.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-N-4-methoxyphenyll-N'-4-methoxyphenyl-acetamidine 在 水 作用下， 以 乙腈 为溶剂， 以87%的产率得到N¹-(4-oxo-2,5-cyclohexadien-1-ylidene)-N²-(4-methoxyphenyl)-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
• 作为产物：
  描述：

  2,2,2-三氟-N-(4-甲氧基苯基)-亚氨基氯化物 、 甲氧苯胺 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以85%的产率得到2,2,2-trifluoro-N-4-methoxyphenyll-N'-4-methoxyphenyl-acetamidine
  参考文献：
  名称：

  由亚氨基酰氯轻松合成α-氟取代的idine及其应用

  摘要：

  从相应的氟化亚氨酰氯合成了一系列α-氟取代的am，收率良好至优异，我们的程序概述了其一些应用。

  DOI：

  10.1016/j.jfluchem.2006.06.008

文献信息

• Synthesis of 2-(Perfluoroalkyl)- and 2-(Perfluoroaryl)benzimidazoles by Oxidative Intramolecular Cyclization of Perfluoroalkyl and Aryl Imidamides
  作者：Masafumi Kobayashi、Kenji Uneyama

  DOI：10.1021/jo952224j

  日期：1996.1.1
• 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.
• Facile synthesis of α-fluoro substituted amidines from imidoyl chlorides and some of its application
  作者：Yong-Ming Wu、Min Zhang、Yi-Qun Li

  DOI：10.1016/j.jfluchem.2006.06.008

  日期：2006.9

  A series of α-fluoro subustituted amidines were synthesized from corresponding fluorinated imidoyl chlorides in good to excellent yields and some of its applications are outlined in our programs.

  从相应的氟化亚氨酰氯合成了一系列α-氟取代的am，收率良好至优异，我们的程序概述了其一些应用。
• 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.