1-hydroxy-2-formylimidazole

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-hydroxy-2-formylimidazole
• 英文别名: 1-hydroxy-1H-imidazole-2-carbaldehyde；1-hydroxyimidazole-2-carbaldehyde
• 化学式: C₄H₄N₂O₂
• 分子量: 112.088
• InChiKey: YCTXHVVYIMEOSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-Benzyloxy-1H-imidazole-2-carbaldehyde 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以97%的产率得到1-hydroxy-2-formylimidazole
  参考文献：
  名称：

  Synthesis of 2-Substituted 1-Hydroxyimidazoles through Directed Lithiation

  摘要：

  Benzylation of 3-hydroxyimidazole 1-oxide gave 3-(benzyloxy)imidazole 1-oxide, which was deoxygenated with phosphorous trichloride to produce 1-(benzyloxy)imidazole. 1-(Benzyloxy)imidazole was deprotonated selectively at C-2 by n-butyllithium. The anion formed was reacted with electrophiles to give 1-(benzyloxy)imidazoles with carbon; halogen, silicon, or sulfur substituents at the 2-position, Subsequent debenzylation afforded 2-substituted 1-hydroxaimidazoles which in turn could be deoxygenated to give 2-substituted imidazoles.

  DOI：

  10.1021/jo970355+

文献信息

• Synthesis of 2-Substituted 1-Hydroxyimidazoles through Directed Lithiation
  作者：Birgitte Langer Eriksen、Per Vedsø、Sandrine Morel、Mikael Begtrup

  DOI：10.1021/jo970355+

  日期：1998.1.1

  Benzylation of 3-hydroxyimidazole 1-oxide gave 3-(benzyloxy)imidazole 1-oxide, which was deoxygenated with phosphorous trichloride to produce 1-(benzyloxy)imidazole. 1-(Benzyloxy)imidazole was deprotonated selectively at C-2 by n-butyllithium. The anion formed was reacted with electrophiles to give 1-(benzyloxy)imidazoles with carbon; halogen, silicon, or sulfur substituents at the 2-position, Subsequent debenzylation afforded 2-substituted 1-hydroxaimidazoles which in turn could be deoxygenated to give 2-substituted imidazoles.

表征谱图