4(5)-<2'-(trifluoromethyl)phenyl>imidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4(5)-<2'-(trifluoromethyl)phenyl>imidazole
• 英文别名: 4-trifluoromethylphenyl-imidazole；5-[2-(trifluoromethyl)phenyl]-1H-imidazole
• 化学式: C₁₀H₇F₃N₂
• 分子量: 212.174
• InChiKey: WBGKZBLPUYAAMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对氟硝基苯 、 4(5)-<2'-(trifluoromethyl)phenyl>imidazole 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4-[4-(4-Trifluoromethylphenyl)-1H-imidazol-1-yl]-nitrobenzene
  参考文献：
  名称：

  PESTICIDAL COMPOSITIONS

  摘要：

  这份文件中披露的发明涉及杀虫剂领域及其在控制害虫方面的应用。披露了一种具有以下结构的化合物。

  公开号：

  US20090209476A1
• 作为产物：
  描述：

  4-重氮咪唑 、 三氟甲苯 以16%的产率得到
  参考文献：
  名称：

  AMICK, T. J.;SHECHTER, H., TETRAHEDRON LETT., 1986, 27, N 8, 901-904

  摘要：

  DOI：

文献信息

• Carbenic reactions of 4-diazo-4-imidazole with benzene derivatives
  作者：T.J. Amick、H. Shechter

  DOI：10.1016/s0040-4039(00)84132-5

  日期：1986.1

  The electrophilic behavior of 4H-imidazolylidene is greatly modified by coordinating groups in benzene derivatives undergoing substitution.

  4H-咪唑基亚烷基的亲电子行为可通过配位进行取代的苯衍生物中的基团大大改变。
• A Convenient Synthesis of Perfluoroalkylated and Fluorinated-Aryl Nitrogen Bases by Electrochemically Induced S_RN1 Substitution
  作者：Maurice Médebielle、Mehmet Ali Oturan、Jean Pinson、Jean-Michel Savéant

  DOI：10.1021/jo9515541

  日期：1996.1.1

  Indirect electrochemical reduction, by means of an aromatic anion mediator, of perfluoroalkyl halides (CF3Br, n-C4F9I, n-C6F13I, I(CF2)(4)I) in the presence of imidazole, 4(5)-nitroimidazole, 2-methyl-5-nitroimidazole, 2-(4'-methoxyphenyl)imidazole, imidazole-2-carboxaldehyde, 4(5)-nitroimidazole-2-carboxaldehyde, 5(6)-nitrobenzimidazole, purines (adenine, hypoxanthine, xanthine, theophylline, lumazine) and pyrimidine anions (uracil, cytosine, barbituric acid) yields the corresponding C-perfluoroalkylated nitrogen bases by an S(RN)1 mechanism. Aromatic nucleophilic substitution of some fluorinated aryl halides 1-iodo-2-(trifluoromethyl)benzene and 1-(4'-iodo-tetrafluorophenyl)-imidazole was also investigated and it was found that 1-iodo-2-(trifluoromethyl)benzene could react successfully under redox-catalyzed conditions with imidazole, 2-(4'-methoxyphenyl)imidazole anion, and uracil anion to give the corresponding 5-(fluorinated-aryl) nitrogen bases. In the case of 1-(4'iodo-tetrafluorophenyl)imidazole, direct electrochemical radical nucleophilic substitution with 2-methyl-5-nitroimidazole and uracil was possible in DMSO. In this way new, 4-[2',3',5',6'-tetrafluoro-4'-(imidazol-1 ''-yl)phenyl] nitrogen bases were obtained in good yields.