3-氯-4-(二氯甲基)吡咯-2,5-二酮 | 339152-94-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 3-氯-4-(二氯甲基)吡咯-2,5-二酮
• 英文名称: 3-Chloro-4-dichloromethyl-pyrrole-2,5-dione
• 英文别名: 1H-Pyrrole-2,5-dione, 3-chloro-4-(dichloromethyl)-；3-chloro-4-(dichloromethyl)pyrrole-2,5-dione
• CAS: 339152-94-2
• 化学式: C₅H₂Cl₃NO₂
• 分子量: 214.435
• InChiKey: GXWFWFCTVZDOHM-UHFFFAOYSA-N

物化性质

• 沸点：
  288.3±40.0 °C(Predicted)
• 密度：
  1.73±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 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

• 作为产物：
  描述：

  3-甲基吡咯-2,5-二酮 在 氯 作用下， 以 四氯化碳 为溶剂， 反应 96.0h， 生成 3-(dichloromethylene)-4,4-dichloro-2,5-pyrrolidinedione 、 3-氯-4-(二氯甲基)吡咯-2,5-二酮
  参考文献：
  名称：

  Halogenated 2,5-pyrrolidinediones: synthesis, bacterial mutagenicity in Ames tester strain TA-100 and semi-empirical molecular orbital calculations

  摘要：

  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.

  DOI：

  10.1016/s1383-5718(00)00129-7

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.