5-[2-(3-(methylcarbamoyl)pyridin-2-yl)pyridin-3-yl]-3-phenyl-1,3,4-oxadiazol-2(3H)-one | 1453118-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-[2-(3-(methylcarbamoyl)pyridin-2-yl)pyridin-3-yl]-3-phenyl-1,3,4-oxadiazol-2(3H)-one
• 英文别名: N-methyl-2-[3-(5-oxo-4-phenyl-1,3,4-oxadiazol-2-yl)pyridin-2-yl]pyridine-3-carboxamide
• CAS: 1453118-41-6
• 化学式: C₂₀H₁₅N₅O₃
• 分子量: 373.371
• InChiKey: SEHBHBHXIURNCV-UHFFFAOYSA-N

物化性质

• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  96.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-甲基甲酰胺 、 1,10-邻二氮杂菲-5,6-二酮 、 benzenediazonium tetrafluoroborate 在 lithium perchlorate 作用下， 反应 5.0h， 以64%的产率得到5-[2-(3-(methylcarbamoyl)pyridin-2-yl)pyridin-3-yl]-3-phenyl-1,3,4-oxadiazol-2(3H)-one
  参考文献：
  名称：

  One-Pot Formation of 1,3,4-Oxadiazol-2(3H)-ones and Dibenzo[c,e]azepines by Concomitant Cathodic Reduction of Diazonium Salts and Phenanthrenequinones

  摘要：

  The one-pot concomitant electrochemical reduction of phenanthrenequinones (1, 2) and arenediazonium salts (3a-f) led to the formation of 1,3,4-oxadiazol-2(3H)-ones (4a-f, 5a) and dibenzo[c,e]azepines (6a-f) when N-methylformamide was used as the solvent. A new pathway, different from those previously described with other aprotic solvents, is proposed. The experimental data support a radical mechanism for the electrochemical process followed by an internal rearrangement to give the products.

  DOI：

  10.1021/jo401264w