3-(dichloromethylene)-4,4-dichloro-2,5-pyrrolidinedione | 165606-93-9

• 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-(dichloromethylene)-4,4-dichloro-2,5-pyrrolidinedione
• 英文别名: 3,3-dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione；3,3-dichloro-4-(dichloromethylidene)pyrrolidine-2,5-dione
• CAS: 165606-93-9
• 化学式: C₅HCl₄NO₂
• 分子量: 248.88
• InChiKey: QURBORJOJALFAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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-(dichloromethylene)-4,4-dichloro-2,5-pyrrolidinedione 在 Rh on carbon 氢气 作用下， 以 苯 为溶剂， 以4.0 mg的产率得到3-(dichloromethylene)-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， 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

文献信息

• Halogenated 2,5-pyrrolidinediones: synthesis, bacterial mutagenicity in Ames tester strain TA-100 and semi-empirical molecular orbital calculations
  作者：Beverly A Freeman、Robert E Wilson、Ronald G Binder、William F Haddon

  DOI：10.1016/s1383-5718(00)00129-7

  日期：2001.2

  The chloroimide 3,3-dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione, a tetrachloroitaconimide, is the principal mutagen produced by chlorination of simulated poultry chiller water. It is the second most potent mutagenic disinfection by-product of chlorination ever reported. Six of seven new synthetic analogs of this compound are direct-acting mutagens in Ames tester strain TA-100. Computed energies of the lowest unoccupied molecular orbital (E-LUMO) and of the radical anion stability (DeltaH(f)(rad) - DeltaH(f)) from MNDO-PM3 for the chloroimides show a quantitative correlation with the Ames TA-100 bacterial mutagenicity values. The molar mutagenicities of these direct acting mutagenic imides having an exocyclic double bond fit the same linear correlation (InMm vs. E-LUMO; In M-m vs. DeltaH(f)(rad) - DeltaH(f)) as the chlorinated 2(5H)-furanones, including the potent mutagen MX, 3-chloro-4-(dichoro-methyl)-5-hydroxy-2(5H)-furanone, a by-product of water chlorination and paper bleaching with chlorine. Mutagenicity data for related haloimides having endocyclic double bonds are also given. For the same number of chlorine atoms, the imides with endocyclic double bonds have significantly higher Ames mutagenicity compared to their structural analogs with exocyclic double bonds, but do not follow the same E-LUMO or DeltaH(f)(rad) - DeltaH(f) correlation as the exocyclic chloroimides and the chlorinated 2(5H)-furanones. Published by Elsevier Science B.V.
• Potent Bacterial Mutagens Produced by Chlorination of Simulated Poultry Chiller Water
  作者：William F. Haddon、Ronald G. Binder、Rosalind Y. Wong、Leslie A. Harden、Robert E. Wilson、Mabry Benson、Kenneth L. Stevens

  DOI：10.1021/jf950076s

  日期：1996.1.1

  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.