3-(4-chlorophenyl)-4-(methylthio)-1H-pyrrole-2,5-dione | 398130-20-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-chlorophenyl)-4-(methylthio)-1H-pyrrole-2,5-dione
• 英文别名: 3-(4-chlorophenyl)-4-methylsulfanylpyrrole-2,5-dione
• CAS: 398130-20-6
• 化学式: C₁₁H₈ClNO₂S
• 分子量: 253.709
• InChiKey: PNOAPSSELOIELI-UHFFFAOYSA-N

物化性质

• 沸点：
  421.6±45.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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-(4-chlorophenyl)-4-(methylthio)-1H-pyrrole-2,5-dione 在 溶剂黄146 、 锌 作用下， 反应 1.0h， 以92%的产率得到3-(4-氯苯基)吡咯烷-2,5-二酮
  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：

  对氯苯乙腈 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 3-(4-chlorophenyl)-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

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，
• 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。
• 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.