3-methyl-3,4,4-trichloro-2,5-pyrrolidinedione | 170660-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-methyl-3,4,4-trichloro-2,5-pyrrolidinedione
• 英文别名: 3,3,4-Trichloro-4-methylpyrrolidine-2,5-dione
• CAS: 170660-65-8
• 化学式: C₅H₄Cl₃NO₂
• 分子量: 216.451
• InChiKey: CUVWLWYZJVAXKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-3,4,4-trichloro-2,5-pyrrolidinedione 在 氯 作用下， 以 四氯化碳 为溶剂， 生成 3-(dichloromethylene)-4,4-dichloro-2,5-pyrrolidinedione
  参考文献：
  名称：

  Potent Bacterial Mutagens Produced by Chlorination of Simulated Poultry Chiller Water

  摘要：

  Hypochlorite treatment of a simulated food-processing mixture produces 3,4-dichloromaleimide and 3,3-dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione (C5HCl4NO2). The tetrachloro compound and two analogs, which can be synthesized from citraconic anhydride and itaconic anhydride, are direct-acting Ames mutagens in Salmonella typhimurium TA100 tester strain. These novel five-carbon cyclic imides are structurally similar to 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX), the principal mutagenic compound present in paper pulp bleaching liquors. Molecular structure analysis of the mutagens was based on X-ray crystallography, C-13 NMR, and mass spectrometry of synthetic chlorinated imides with identical. mass spectra and gas chromatographic retention indices. The tetrachloroimide accounts for much of the mutagenicity of the dichloromethane-extractable pH 2 fraction from chlorination of a simulated food-processing system consisting of chicken frankfurters. In the Ames TA100 tester strain it has a molecular mutagenicity of 1450 revertants/nmol without microsomal activation, making it the second most potent mutagen reported from a chlorination process.

  DOI：

  10.1021/jf950076s
• 作为产物：
  描述：

  3-氯-4-甲基吡咯-2,5-二酮 在 氯 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 以93%的产率得到3-methyl-3,4,4-trichloro-2,5-pyrrolidinedione
  参考文献：
  名称：

  Potent Bacterial Mutagens Produced by Chlorination of Simulated Poultry Chiller Water

  摘要：

  Hypochlorite treatment of a simulated food-processing mixture produces 3,4-dichloromaleimide and 3,3-dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione (C5HCl4NO2). The tetrachloro compound and two analogs, which can be synthesized from citraconic anhydride and itaconic anhydride, are direct-acting Ames mutagens in Salmonella typhimurium TA100 tester strain. These novel five-carbon cyclic imides are structurally similar to 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX), the principal mutagenic compound present in paper pulp bleaching liquors. Molecular structure analysis of the mutagens was based on X-ray crystallography, C-13 NMR, and mass spectrometry of synthetic chlorinated imides with identical. mass spectra and gas chromatographic retention indices. The tetrachloroimide accounts for much of the mutagenicity of the dichloromethane-extractable pH 2 fraction from chlorination of a simulated food-processing system consisting of chicken frankfurters. In the Ames TA100 tester strain it has a molecular mutagenicity of 1450 revertants/nmol without microsomal activation, making it the second most potent mutagen reported from a chlorination process.

  DOI：

  10.1021/jf950076s