1-benzyl-2-methyl-1H-imidazo[4,5-b]pyridine 4-oxide | 1137089-69-0

• 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-benzyl-2-methyl-1H-imidazo[4,5-b]pyridine 4-oxide
• CAS: 1137089-69-0
• 化学式: C₁₄H₁₃N₃O
• 分子量: 239.277
• InChiKey: INOVRHGDUIHYKE-UHFFFAOYSA-N

物化性质

• 熔点：
  194-196 °C
• 沸点：
  482.3±47.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-methyl-3H-imidazo[4,5-b]pyridine-4-oxide 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 3-benzyl-2-methyl-3H-imidazo[4,5-b]pyridine 4-oxide 、 1-benzyl-2-methyl-1H-imidazo[4,5-b]pyridine 4-oxide
  参考文献：
  名称：

  Regioselective N-alkylation of imidazo[4,5-b]pyridine-4-oxide derivatives: an experimental and DFT study

  摘要：

  Regioselectivities were determined for N-alkylations of imidazo[4,5-bipyridine-4-oxide and 2-methyl-imidazo[4,5-b]pyridme-4-oxide with benzyl bromide or benzyl iodide at RT using K2CO3 in DMF as a base. Experimental attempts have shown that N-1/N-3 ratios slightly varied according to the Substitution on C-2 position. This was confirmed by DFT calculations in solvent phase. This computational study has shown first that this N-benzylation reaction passed through a S(N)2 mechanism. Moreover, regioselectivity of N-benzylation has appeared essentially governed by 'steric approach control'. It explained that opposite N-1/N-3 ratios were obtained with imidazo[4,5-b]pyridine-4-oxide and its 2-methyl-substituted analog. Finally, regioselectivities slightly varied with the nature of benzyl halide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.006