2-(1-butyl-2-methyl-4-nitro-1H-imidazol-5-yl)-4,5-dimethoxybenzaldehyde

• 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-(1-butyl-2-methyl-4-nitro-1H-imidazol-5-yl)-4,5-dimethoxybenzaldehyde
• 英文别名: 2-(3-Butyl-2-methyl-5-nitroimidazol-4-yl)-4,5-dimethoxybenzaldehyde；2-(3-butyl-2-methyl-5-nitroimidazol-4-yl)-4,5-dimethoxybenzaldehyde
• 化学式: C₁₇H₂₁N₃O₅
• 分子量: 347.371
• InChiKey: SIGPNQLWTVKYAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  99.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(1-butyl-2-methyl-4-nitro-1H-imidazol-5-yl)-4,5-dimethoxybenzaldehyde 在 10 mol% palladium on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以68%的产率得到1-butyl-7,8-dimethoxy-2-methyl-1H-imidazo[4,5-c]isoquinoline
  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：

  6-溴藜芦醛 、 1-正-丁基-2-甲基-4-硝基咪唑 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium 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85%的产率得到2-(1-butyl-2-methyl-4-nitro-1H-imidazol-5-yl)-4,5-dimethoxybenzaldehyde
  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