1-(difluoromethyl)-5-methoxy-1H-benzo[d]imidazole | 1501993-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(difluoromethyl)-5-methoxy-1H-benzo[d]imidazole
• 英文别名: 1-(Difluoromethyl)-5-methoxybenzimidazole；1-(difluoromethyl)-5-methoxybenzimidazole
• CAS: 1501993-66-3
• 化学式: C₉H₈F₂N₂O
• 分子量: 198.172
• InChiKey: FKGVJRLAJYBWFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  27.05
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  三氟甲烷 、 5-甲氧基苯并咪唑 在 potassium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 3.5h， 生成 1-(difluoromethyl)-6-methoxy-1H-benzo[d]imidazole 、 1-(difluoromethyl)-5-methoxy-1H-benzo[d]imidazole
  参考文献：
  名称：

  Use of fluoroform as a source of difluorocarbene in the synthesis of N -CF 2 H heterocycles and difluoromethoxypyridines

  摘要：

  Fluoroform is used as a source of difluorocarbene to convert various N-, O-, and C-nucleophiles to their difluoromethylated derivatives. Imidazole, benzimidazole, benztriazole, hydroxypyridines, and their derivatives underwent reaction at moderate temperatures and atmospheric pressure, using potassium hydroxide as base in a two-phase (water/acetonitrile) process to provide moderate to good yields of the respective products. Nitrophenols required addition of a co-solvent (methanol) to obtain good yields of products. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.08.015

文献信息

• <i>N</i>-Difluoromethylation of Imidazoles and Benzimidazoles Using the Ruppert–Prakash Reagent under Neutral Conditions
  作者：G. K. Surya Prakash、Sankarganesh Krishnamoorthy、Somesh K. Ganesh、Aditya Kulkarni、Ralf Haiges、George A. Olah

  DOI：10.1021/ol403007j

  日期：2014.1.3

  using TMS-CF3 (the Ruppert–Prakash reagent) under neutral conditions. Difluoromethylated products were obtained in good-to-excellent yields. Inexpensive, commercially available starting materials, neutral conditions, and shorter reaction times are advantages of this methodology. Reactions are accessible through conventional as well as microwave irradiation conditions.

  使用TMS-CF 3（Ruppert-Prakash试剂）在中性条件下已实现了咪唑和苯并咪唑的直接N-二氟甲基化。以良好至优异的产率获得二氟甲基化产物。廉价的市售起始原料，中性条件和较短的反应时间是该方法的优点。可通过常规以及微波辐射条件进行反应。