3-氯-4-甲基吡咯-2,5-二酮 | 69636-50-6

• 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-甲基吡咯-2,5-二酮
• 英文名称: 2-chloro-3-methylmaleimide
• 英文别名: 3-Chloro-4-methyl-1H-pyrrole-2,5-dione；3-chloro-4-methylpyrrole-2,5-dione
• CAS: 69636-50-6
• 化学式: C₅H₄ClNO₂
• 分子量: 145.545
• InChiKey: PSOSICZGLLPDFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 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-氯-4-甲基吡咯-2,5-二酮 在 溴 、 三氟乙酸 作用下， 反应 168.0h， 生成 3-Bromomethyl-4-chloro-pyrrole-2,5-dione
  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
• 作为产物：
  描述：

  3-甲基吡咯-2,5-二酮 在 氯 作用下， 以 水 为溶剂， 生成 3-氯-4-甲基吡咯-2,5-二酮
  参考文献：
  名称：

  The relationship between the Broensted acidities of imides and their hydrogen-bonding acidities toward oxygen bases

  摘要：

  DOI：

  10.1021/jo00239a041

文献信息

• SUBSTITUTED TETRAHYDROQUINOLINES
  申请人：Schiemann Kai

  公开号：US20100022579A1

  公开（公告）日：2010-01-28

  Compounds of the formula (I), in which R 1 , R 2 , R 3 , R 4 , R 5 , X, Y, W, Q 1 , Q 2 , Z, s and m have the meanings indicated in claim 1, can be employed, inter alia, for the treatment of tumours.

  化合物的结构式（I）中，其中R1、R2、R3、R4、R5、X、Y、W、Q1、Q2、Z、s和m具有权利要求书中指定的含义，可用于治疗肿瘤。
• Plant growth regulation
  申请人：Bastiaans Henricus M.M.

  公开号：US20100152044A1

  公开（公告）日：2010-06-17

  The present invention relates to the use of a compound for plant growth regulation, preferably by application of the compound to plants, to the seeds from which they grow or to the locus in which they grow, in an effective plant growth regulating, preferably non-phytotoxic amount, which compound is a 3,4-disubstituted maleimide derivative of formula (I) or an agriculturally acceptable salt thereof, wherein: X is aryl or heteroaryl which groups are unsubstituted or substituted; Y is NH or a covalent bond; and Z is aryl or heteroaryl which groups are unsubstituted or substituted and a method for treatment of plants with such compounds in order to induce growth regulating responses.

  本发明涉及一种用于植物生长调节的化合物的使用，优选地通过将该化合物施用于植物、它们生长的种子或它们生长的部位，以有效的植物生长调节，优选地是非植物毒性量。该化合物是式（I）的3,4-二取代马来酰亚胺衍生物或其农业上可接受的盐，其中：X为芳基或杂环芳基，这些基团未取代或取代；Y为NH或共价键；Z为芳基或杂环芳基，这些基团未取代或取代。本发明还涉及使用此类化合物处理植物以诱导生长调节反应的方法。
• 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.
• The relationship between the Broensted acidities of imides and their hydrogen-bonding acidities toward oxygen bases
  作者：Jack Hine、Soonkap Hahn、Jeongsug Hwang

  DOI：10.1021/jo00239a041

  日期：1988.2
• 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.