1-Methyl-3-methylsulfanyl-4-naphthalen-1-yl-pyrrole-2,5-dione | 398130-33-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Methyl-3-methylsulfanyl-4-naphthalen-1-yl-pyrrole-2,5-dione
• 英文别名: 1-Methyl-3-methylsulfanyl-4-naphthalen-1-ylpyrrole-2,5-dione
• CAS: 398130-33-1
• 化学式: C₁₆H₁₃NO₂S
• 分子量: 283.351
• InChiKey: QLIJCOLHVNXDCG-UHFFFAOYSA-N

物化性质

• 沸点：
  468.8±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Methyl-3-methylsulfanyl-4-naphthalen-1-yl-pyrrole-2,5-dione 在 溶剂黄146 、 锌 作用下， 反应 1.0h， 以82%的产率得到N-methyl-2-(1-naphthyl)succinimide
  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 盐酸 、 sodium hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 、 丙酮 为溶剂， 生成 1-Methyl-3-methylsulfanyl-4-naphthalen-1-yl-pyrrole-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