2-(1-methyl-1H-pyrrol-2-yl)-oxazole-5-carbaldehyde | 1033037-44-3

• 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-methyl-1H-pyrrol-2-yl)-oxazole-5-carbaldehyde
• 英文别名: 2-(1-Methyl-1H-pyrrol-2-YL)oxazole-5-carbaldehyde；2-(1-methylpyrrol-2-yl)-1,3-oxazole-5-carbaldehyde
• CAS: 1033037-44-3
• 化学式: C₉H₈N₂O₂
• 分子量: 176.175
• InChiKey: FKFZOJWHWKDGAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-propargyl-1-methyl-1H-pyrrole-2-carboxamide 在 双(乙腈)氯化钯(II) 氧气 、 copper dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以39%的产率得到2-(1-methyl-1H-pyrrol-2-yl)-oxazole-5-carbaldehyde
  参考文献：
  名称：

  Intramolecular Pd(II)-Catalyzed Cyclization of Propargylamides: Straightforward Synthesis of 5-Oxazolecarbaldehydes

  摘要：

  Direct synthesis of 2-substituted 5-oxazolecarbaldehydes was performed by intramolecular reaction of propargylamides through treatment with a catalytic amount of Pd(II) salts in the presence of a stoichiometric amount of reoxidant agent. The heterocyclization process was well-tolerated by a wide range of aryl, heteroaryl, and alkyl propargylamides. This protocol constitutes a valuable synthetic pathway to 5-oxazolecarbaldehydes, alternative to the formylation on oxazole rings, often unsatisfactory in term of regioselectivity and yields.

  DOI：

  10.1021/jo800621n