1-(4-methoxyphenyl)-4-tosyl-5-(trifluoromethyl)-1H-imidazoles | 1613146-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-methoxyphenyl)-4-tosyl-5-(trifluoromethyl)-1H-imidazoles
• 英文别名: 1-(4-methoxyphenyl)-4-(4-methylbenzenesulfonyl)-5-(trifluoromethyl)-1H-imidazole；1-(4-methoxyphenyl)-4-tosyl-5-(trifluoromethyl)-1H-imidazole；1-(4-Methoxyphenyl)-4-(4-methylphenyl)sulfonyl-5-(trifluoromethyl)imidazole；1-(4-methoxyphenyl)-4-(4-methylphenyl)sulfonyl-5-(trifluoromethyl)imidazole
• CAS: 1613146-18-1
• 化学式: C₁₈H₁₅F₃N₂O₃S
• 分子量: 396.39
• InChiKey: FVZYDUOYVQPAHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  对甲基苯磺酰甲基异腈 、 2,2,2-三氟-N-(4-甲氧基苯基)-亚氨基氯化物 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以97%的产率得到1-(4-methoxyphenyl)-4-tosyl-5-(trifluoromethyl)-1H-imidazoles
  参考文献：
  名称：

  碱介导的[3 + 2]环三氟乙酰亚胺氯和异氰酸酯的环取代：一种改进的5-三氟甲基咪唑区域选择性合成的方法

  摘要：

  已经开发了由t -BuOK介导的三氟乙酰亚胺基氯与活性亚甲基异氰酸酯的[3 + 2]环加成反应，用于合成5-三氟甲基-咪唑。在温和的反应条件下，在t- BuOK存在下，转化过程平稳进行，从而高效地提供了一系列结构多样的5-三氟甲基-咪唑。

  DOI：

  10.1016/j.tet.2020.131168

文献信息

• 1-Imidoyl-1,2,3-benzotriazoles—Novel Reagents for the Synthesis of 1-Aryl-5-trifluoromethylimidazoles
  作者：A. S. Bunev、E. V. Varakina、D. A. Khochenkov、A. S. Peregudov

  DOI：10.1134/s1070428019040122

  日期：2019.4

  1-Imidoylbenzotriazoles [N-aryl-1-(1H-benzotriazol-1-yl)-2,2,2-trifluoroethan-1-imines] reacted with tosylmethyl isocyanide according to van Leusen's procedure to give difficultly accessible 1-aryl-4-(4-methylbenzenesulfonyl)-5-(trifluoromethyl)-1H-imidazoles in good yields (81-94%). The initial imidoylbenzotriazoles were conveniently synthesized by reaction of sodium benzotriazolide with the corresponding imidoyl chlorides in THF. The reactions were carried out with a wide series of imidoylbenzotriazoles containing various electron-donating and electron-withdrawing substituents in the N-aryl fragment.
• Synthesis of 1-aryl-4-tosyl-5-(trifluoromethyl)-1H-imidazoles
  作者：Alexander S. Bunev、Maksim A. Vasiliev、Vladimir E. Statsyuk、Gennady I. Ostapenko、Alexander S. Peregudov

  DOI：10.1016/j.jfluchem.2014.04.013

  日期：2014.7

  A new synthetic protocol for the synthesis of 1,4,5-trisubstituted imidazoles containing trifluoromethyl group has been developed using van Leusen reaction, which incorporates two-component condensation reaction trifluoroacetimidoyl chlorides with tosylmethylisocyanide. This protocol provides a novel and improved method for obtaining trifluoromethyl containing 1,4,5-trisubstituted imidazoles in good yields. (C) 2014 Elsevier B.V. All rights reserved.