2-methyl-4-nitro-1-(2-phenoxyethyl)-1H-imidazole | 16183-76-9

• 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-4-nitro-1-(2-phenoxyethyl)-1H-imidazole
• 英文别名: 2-methyl-4-nitro-1-(2-phenoxy-ethyl)-1H-imidazole；1-<2-Phenoxy-ethyl>-2-methyl-4-nitro-imidazol；Imidazole, 2-methyl-4-nitro-1-(phenoxyethyl)-；2-methyl-4-nitro-1-(2-phenoxyethyl)imidazole
• CAS: 16183-76-9
• 化学式: C₁₂H₁₃N₃O₃
• 分子量: 247.254
• InChiKey: MMIWYYDIEDIIGY-UHFFFAOYSA-N

物化性质

• 沸点：
  458.1±25.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-4-nitro-1-(2-phenoxyethyl)-1H-imidazole 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 silver carbonate 、 三甲基乙酸 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 14.0h， 以76%的产率得到3-methyl-1-nitro-5,6-dihydrobenzo[f ]imidazo[1,5-d][1,4]oxazepine
  参考文献：
  名称：

  Transition-Metal-Catalyzed Arylation of Nitroimidazoles and Further Transformations of Manipulable Nitro Group

  摘要：

  Pd- or Ni-catalyzed CH arylation of 4-nitroimidazole derivatives directed by a manipulable nitro group was developed. The reaction tolerates a wide range of substituted aryl halides and 4-nitroimidazoles. The experiments indicated that the nitro group has influence on regioselectivity of the reaction. In addition, we have shown that the efficiency of the SuzukiMiyaura cross-coupling reaction of nitroimidazoles is slightly lower in comparison to the direct CH arylation. The exploration of the chemical potential of the nitro group and a putative reaction mechanism are discussed.

  DOI：

  10.1021/jo5025927
• 作为产物：
  描述：

  2-甲基-4-硝基咪唑 、 2-苯氧乙基溴 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以89%的产率得到2-methyl-4-nitro-1-(2-phenoxyethyl)-1H-imidazole
  参考文献：
  名称：

  Transition-Metal-Catalyzed Arylation of Nitroimidazoles and Further Transformations of Manipulable Nitro Group

  摘要：

  Pd- or Ni-catalyzed CH arylation of 4-nitroimidazole derivatives directed by a manipulable nitro group was developed. The reaction tolerates a wide range of substituted aryl halides and 4-nitroimidazoles. The experiments indicated that the nitro group has influence on regioselectivity of the reaction. In addition, we have shown that the efficiency of the SuzukiMiyaura cross-coupling reaction of nitroimidazoles is slightly lower in comparison to the direct CH arylation. The exploration of the chemical potential of the nitro group and a putative reaction mechanism are discussed.

  DOI：

  10.1021/jo5025927