5-(hydroxyamino)-3-(2-methoxyphenyl)-4-methylsulfanylpyrrol-2-one | 398130-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(hydroxyamino)-3-(2-methoxyphenyl)-4-methylsulfanylpyrrol-2-one
• CAS: 398130-09-1
• 化学式: C₁₂H₁₂N₂O₃S
• 分子量: 264.305
• InChiKey: SPXVWJFPACZGSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.92
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(hydroxyamino)-3-(2-methoxyphenyl)-4-methylsulfanylpyrrol-2-one 在 盐酸 作用下， 以 甲醇 为溶剂， 以84%的产率得到3-(2-methoxyphenyl)-4-(methylthio)-1H-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
• 作为产物：
  描述：

  邻甲氧基苯乙腈 在 sodium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 5-(hydroxyamino)-3-(2-methoxyphenyl)-4-methylsulfanylpyrrol-2-one
  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

文献信息

• Synthesis of 3-Methylthio-4-aryl-3-pyrroline-2,5-diones and 3-Arylpyrrolidine-2,5-diones by Reaction of Nitroketene Dithioacetal with Arylacetonitriles
  作者：Yasuhiro Shigemitsu、Yoshinori Tominaga

  DOI：10.3987/com-01-9336

  日期：——

  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.