3-(methylthio)-4-(thiophen-2-yl)-1H-pyrrole-2,5-dione | 398130-24-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-(methylthio)-4-(thiophen-2-yl)-1H-pyrrole-2,5-dione
• 英文别名: 3-Methylsulfanyl-4-thiophen-2-ylpyrrole-2,5-dione
• CAS: 398130-24-0
• 化学式: C₉H₇NO₂S₂
• 分子量: 225.292
• InChiKey: GPQFYFAVBPWGLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  99.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(methylthio)-4-(thiophen-2-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 1-Methyl-3-(2-thienyl)-pyrrolidin-2,5-dion
  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：

  2-噻吩乙腈 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 3-(methylthio)-4-(thiophen-2-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

• Diverse 3-Methylthio-4-Substituted Maleimides through a Novel Rearrangement Reaction: Synthesis and Selective Cell Imaging
  作者：Luan V. Meirelles、Pedro P. de Castro、Saulo T. A. Passos、Bernardo B. P. P. Carvalho、Chris H. J. Franco、José R. Correa、Brenno A. D. Neto、Giovanni W. Amarante

  DOI：10.1021/acs.joc.1c02714

  日期：2022.3.4

  metal-free protocol for the preparation of fluorescent and non-fluoresent 3-methylthio-4-arylmaleimides in a single step through a new rearrangement from thiazolidine-2,4-diones is described. By employing the optimized reaction conditions, a broad scope of derivatives was prepared in ≤97% yield. The reaction tolerated several substituted aryl groups, including the challenging preparation of pyridyl-containing

  描述了通过从 thiazolidine-2,4-diones 进行新的重排，一步制备荧光和非荧光 3-methylthio-4-arylmaleimides 的无过渡金属协议。通过采用优化的反应条件，以≤97%的收率制备了广泛的衍生物。该反应耐受几个取代的芳基，包括具有挑战性的含吡啶基衍生物的制备。一系列对照实验强烈表明新的重排涉及关键的异氰酸酯中间体和与原位生成的甲基硫代甲基乙酸酯的进一步反应。还研究了一些合成衍生物的光物理性质及其在活细胞成像中的用途，
• 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.