1-(4-chlorophenyl)-4-tosyl-5-(trifluoromethyl)-1H-imidazoles | 1613146-20-5

• 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-chlorophenyl)-4-tosyl-5-(trifluoromethyl)-1H-imidazoles
• 英文别名: 1-(4-chlorophenyl)-4-(4-methylbenzenesulfonyl)-5-(trifluoromethyl)-1H-imidazole；1-(4-chlorophenyl)-4-tosyl-5-(trifluoromethyl)-1H-imidazole；1-(4-Chlorophenyl)-4-(4-methylphenyl)sulfonyl-5-(trifluoromethyl)imidazole；1-(4-chlorophenyl)-4-(4-methylphenyl)sulfonyl-5-(trifluoromethyl)imidazole
• CAS: 1613146-20-5
• 化学式: C₁₇H₁₂ClF₃N₂O₂S
• 分子量: 400.809
• InChiKey: ILKRKRAGZSEZMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(4-chlorophenyl)-2,2,2-trifluoroacetimidoyl chloride 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.75h， 生成 1-(4-chlorophenyl)-4-tosyl-5-(trifluoromethyl)-1H-imidazoles
  参考文献：
  名称：

  1-Imidoyl-1,2,3-benzotriazoles—Novel Reagents for the Synthesis of 1-Aryl-5-trifluoromethylimidazoles

  摘要：

  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.

  DOI：

  10.1134/s1070428019040122

文献信息

• Base-mediated [3+2] annulation of trifluoroacetimidoyl chlorides and isocyanides: An improved approach for regioselective synthesis of 5-trifluoromethyl-imidazoles
  作者：Sipei Hu、Hefei Yang、Zhengkai Chen、Xiao-Feng Wu

  DOI：10.1016/j.tet.2020.131168

  日期：2020.5

  A t-BuOK-mediated [3 + 2] cycloaddition reaction of trifluoroacetimidoyl chlorides and active methylene isocyanides for the synthesis of 5-trifluoromethyl-imidazoles has been developed. Under mild reaction conditions, the transformation proceeds smoothly in the presence of t-BuOK to afford an array of structurally diverse 5-trifluoromethyl-imidazoles with high efficiency.

  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。
• 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.
• 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.