3-Methylsulfanyl-4-naphthalen-1-yl-pyrrole-2,5-dione 2-oxime | 398130-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-Methylsulfanyl-4-naphthalen-1-yl-pyrrole-2,5-dione 2-oxime
• 英文别名: 5-(hydroxyamino)-4-methylsulfanyl-3-naphthalen-1-ylpyrrol-2-one
• CAS: 398130-14-8
• 化学式: C₁₅H₁₂N₂O₂S
• 分子量: 284.338
• InChiKey: ZSZSUTNRVWYYLH-UHFFFAOYSA-N

物化性质

• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  61.69
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-Methylsulfanyl-4-naphthalen-1-yl-pyrrole-2,5-dione 2-oxime 在 溶剂黄146 、 锌 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以91%的产率得到3-(naphthalen-1-yl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  Synthesis of 3-Methylthio-4-aryl-3-pyrroline-2,5-diones and 3-Arylpyrrolidine-2,5-diones by Reaction of Nitroketene Dithioacetal with Arylacetonitriles

  摘要：

  The reaction of nitroketene dithioacetal (1a), i.e., 2,2-bis(methylthio)-1-nitroethylene, with arylacetonitriles (2a-I) in the presence of the base like sodium hydroxide gave 4-nitrobut-2-enenitriles (3a-I) which were converted into 5-hydroxyimino-4-methylthio-3-phenyl-3-pyrrolin-2-ones (4a-i) under refluxing in methanol. Title compounds (5a-i) were readily obtained by the treatment of 4a-i with hydrochloric acid and were finally led to N-methylated products (6a-I) with methyl iodide. The reduction of maleimides (4-6) with zinc dust in acetic acid afforded the corresponding 3-arylpyrrolidine-2,5-diones (7a-i) that can be converted to pharmacologycally active compounds like mesembrines.

  DOI：

  10.3987/com-01-9336
• 作为产物：
  描述：

  1-萘乙腈 在 sodium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 3-Methylsulfanyl-4-naphthalen-1-yl-pyrrole-2,5-dione 2-oxime
  参考文献：
  名称：

  Synthesis of 3-Methylthio-4-aryl-3-pyrroline-2,5-diones and 3-Arylpyrrolidine-2,5-diones by Reaction of Nitroketene Dithioacetal with Arylacetonitriles

  摘要：

  The reaction of nitroketene dithioacetal (1a), i.e., 2,2-bis(methylthio)-1-nitroethylene, with arylacetonitriles (2a-I) in the presence of the base like sodium hydroxide gave 4-nitrobut-2-enenitriles (3a-I) which were converted into 5-hydroxyimino-4-methylthio-3-phenyl-3-pyrrolin-2-ones (4a-i) under refluxing in methanol. Title compounds (5a-i) were readily obtained by the treatment of 4a-i with hydrochloric acid and were finally led to N-methylated products (6a-I) with methyl iodide. The reduction of maleimides (4-6) with zinc dust in acetic acid afforded the corresponding 3-arylpyrrolidine-2,5-diones (7a-i) that can be converted to pharmacologycally active compounds like mesembrines.

  DOI：

  10.3987/com-01-9336