N-methyldibenzo[c,e]azepine-5-one-7-(ylidene-2-(4-methoxyphenyl)hydrazine)

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: N-methyldibenzo[c,e]azepine-5-one-7-(ylidene-2-(4-methoxyphenyl)hydrazine)
• 化学式: C₂₂H₁₉N₃O₂
• 分子量: 357.412
• InChiKey: BNOZWGYUCRXFNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.62
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  N-甲基甲酰胺 、 4-methoxybenzenediazonium tetrafluoroborate 、 菲醌 在 四丁基高氯酸铵 作用下， 反应 5.0h， 以8%的产率得到5-[2-(2'-(methylcarbamoyl)phenyl)phenyl]-3-(4-methoxyphenyl)-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

文献信息

• One-Pot Formation of 1,3,4-Oxadiazol-2(3<i>H</i>)-ones and Dibenzo[<i>c</i>,<i>e</i>]azepines by Concomitant Cathodic Reduction of Diazonium Salts and Phenanthrenequinones
  作者：Belen Batanero、Fructuoso Barba、Avelino Martin

  DOI：10.1021/jo401264w

  日期：2013.9.20

  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.