1-(4-trifluoromethyl-2-cyanophenyl)-1H-imidazole | 25373-51-7

• 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-trifluoromethyl-2-cyanophenyl)-1H-imidazole
• 英文别名: 1-(2-Cyan-4-trifluormethylphenyl)imidazol；2-imidazol-1-yl-5-trifluoromethyl-benzonitrile；Benzonitrile, 2-(1H-imidazol-1-yl)-5-(trifluoromethyl)-；2-imidazol-1-yl-5-(trifluoromethyl)benzonitrile
• CAS: 25373-51-7
• 化学式: C₁₁H₆F₃N₃
• mdl: MFCD11206712
• 分子量: 237.184
• InChiKey: SDEZBFJKBZCCIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  咪唑 、 2-氯-4-三氟甲基苯腈 在 trans-1,2-diaminocyclohexane-based copper(II) complex potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以95%的产率得到1-(4-trifluoromethyl-2-cyanophenyl)-1H-imidazole
  参考文献：
  名称：

  N‐Arylation of Heterocycles with Chloro‐ and Fluoroarenes using Resin‐Supported Sulfonato‐Cu(salen) Complex

  摘要：

  Sulfonato-Cu(salen) complex immobilized onto a Merrifield's resin was found to be an efficient catalyst for the N-arylation of heterocycles with electron-withdrawing hloro- and fluoroarenes. The reactions were carried out in the presence of an inexpensive mild base, K2CO3, and N-arylated compounds were obtained in good to excellent yields. The catalyst was recovered by simple filtration and reused for three cycles with almost consistent activity.

  DOI：

  10.1080/00397910701798218

文献信息

• Design and Evolution of Copper Apatite Catalysts for N<i>-</i>Arylation of Heterocycles with Chloro- and Fluoroarenes
  作者：Boyapati M. Choudary、Chidara Sridhar、Mannepalli L. Kantam、Gopaldasu T. Venkanna、Bojja Sreedhar

  DOI：10.1021/ja0436594

  日期：2005.7.1

  with Cu(II). These basic copper catalysts catalyzed N-arylation of imidazoles and other heterocycles with chloroarenes and electron-poor fluoroarenes in good to excellent yields. Synthesis and characterization of some of the intermediates of the catalytic cycle gave some insight into the mechanism of the very important organic transformation. The necessity of basic sites for the activation of C-Cl

  我们报告了通过共沉淀和随后与 Cu(II) 交换将碱性物质 F-/tBuO- 原位掺入磷灰石中，制备可回收的多相催化剂、铜交换氟磷灰石和铜交换叔丁氧基磷灰石。这些碱性铜催化剂催化咪唑和其他杂环与氯芳烃和缺电子氟芳烃的 N-芳基化反应，产率非常好。催化循环的一些中间体的合成和表征使人们对非常重要的有机转化的机制有了一些了解。在杂环与卤代芳烃的 N-芳基化过程中，用于激活 C-Cl 和 CF 键的碱性位点的必要性是公认的。