3-(methylthio)-4-(naphthalen-1-yl)-1H-pyrrole-2,5-dione | 398130-23-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(methylthio)-4-(naphthalen-1-yl)-1H-pyrrole-2,5-dione
• 英文别名: 3-Methylsulfanyl-4-naphthalen-1-ylpyrrole-2,5-dione
• CAS: 398130-23-9
• 化学式: C₁₅H₁₁NO₂S
• 分子量: 269.324
• InChiKey: DYOPYXPHQXMPKY-UHFFFAOYSA-N

物化性质

• 沸点：
  492.3±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(methylthio)-4-(naphthalen-1-yl)-1H-pyrrole-2,5-dione 在 potassium carbonate 、 溶剂黄146 、 锌 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 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 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 3-(methylthio)-4-(naphthalen-1-yl)-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

文献信息

• Convergent integration of three self-sorting domino sequences: three-component direct synthesis of 3-methylthio-4-aryl-maleimides from methyl ketones with acetonitrile and DMSO
  作者：Qinghe Gao、Shan Liu、Xia Wu、Anxin Wu

  DOI：10.1016/j.tetlet.2014.09.099

  日期：2014.11

  converted to DMS in situ, which subsequently served as a methylthiolation reagent in the reaction. To the best of our knowledge, this protocol provided the first known example of convergent integration of three self-sorting domino sequences.

  描述了由I 2促进的三组分偶联反应，用于由甲基酮与乙腈和DMSO构建3-（甲硫基）-4-芳基-1 H-吡咯-2,5-二酮。该转化涉及α-酮酰亚胺的原位产生和应用。此外，DMSO原位转化为DMS，随后在反应中用作甲基硫醇化试剂。据我们所知，该协议提供了三个自排序多米诺骨牌序列的融合整合的第一个已知示例。