2-methyl-1-(2,3,5,6-tetrafluorophenyl)-1H-imidazole | 1262133-95-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methyl-1-(2,3,5,6-tetrafluorophenyl)-1H-imidazole
• 英文别名: 2-Methyl-1-(2,3,5,6-tetrafluorophenyl)imidazole
• CAS: 1262133-95-8
• 化学式: C₁₀H₆F₄N₂
• 分子量: 230.165
• InChiKey: AFPOZSLWPUMHJN-UHFFFAOYSA-N

物化性质

• 熔点：
  131-135 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  303.9±52.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 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：
  17.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-甲基咪唑 、 2,3,4,5,6-五氟碘苯 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以85%的产率得到2-methyl-1-(2,3,5,6-tetrafluorophenyl)-1H-imidazole
  参考文献：
  名称：

  Transition-Metal-Free O-, S-, and N-Arylation of Alcohols, Thiols, Amides, Amines, and Related Heterocycles

  摘要：

  A new protocol for the Ullmann-type arylation process of different aromatic heterocycles without any transition-metal catalyst, implying the use of a combination of an excess of potassium hydroxide and dimethyl sulfoxide, is described. The reaction can be performed between a broad range of starting nucleophiles including phenol, alcohols, amines, nitrogen-containing five-membered systems such as pyrazoles, imidazoles, and indoles, and amides with haloarenes, iodide and bromide derivatives giving the best results, the possible pathway involving the in situ generation of the corresponding benzyne intermediate. When the reaction was performed with 2-iodoaniline and either carboxarnides or isothiocyanato derivatives, the corresponding benzoazole derivatives were obtained.

  DOI：

  10.1021/jo1022052

文献信息

• Transition-Metal-Free <i>O</i>-, <i>S</i>-, and <i>N</i>-Arylation of Alcohols, Thiols, Amides, Amines, and Related Heterocycles
  作者：Rafael Cano、Diego J. Ramón、Miguel Yus

  DOI：10.1021/jo1022052

  日期：2011.1.21

  A new protocol for the Ullmann-type arylation process of different aromatic heterocycles without any transition-metal catalyst, implying the use of a combination of an excess of potassium hydroxide and dimethyl sulfoxide, is described. The reaction can be performed between a broad range of starting nucleophiles including phenol, alcohols, amines, nitrogen-containing five-membered systems such as pyrazoles, imidazoles, and indoles, and amides with haloarenes, iodide and bromide derivatives giving the best results, the possible pathway involving the in situ generation of the corresponding benzyne intermediate. When the reaction was performed with 2-iodoaniline and either carboxarnides or isothiocyanato derivatives, the corresponding benzoazole derivatives were obtained.