(chloromethyl)maleic anhydride | 41702-49-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (chloromethyl)maleic anhydride
• 英文别名: Chlormethyl-maleinsaeureanhydrid；Chlorcitraconsaureanhydrid；3-(chloromethyl)furan-2,5-dione
• CAS: 41702-49-2
• 化学式: C₅H₃ClO₃
• mdl: MFCD19232132
• 分子量: 146.53
• InChiKey: TYWOWSOZRSULNC-UHFFFAOYSA-N

物化性质

• 熔点：
  28-28.5 °C
• 沸点：
  113-115 °C(Press: 11 Torr)
• 密度：
  1.518±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (chloromethyl)maleic anhydride 生成 3-chloromethyl-3,4-dichlorosuccinic anhydride
  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：

  2-chloro-2-chloromethyl-succinic acid anhydride 生成 (chloromethyl)maleic anhydride
  参考文献：
  名称：

  取代的马来酸酐与1-乙烯基环己烷的狄尔斯-阿尔德反应：立体定向形成双环中间体，可用于合成环戊烷二萜

  摘要：

  1-乙烯基环己烯与乌头酸酐的Diels-Alder反应产生加合物5b，其具有与Alder内定律所预测的相反的立体化学。另一方面，与氯甲基马来酸酐和柠康酸酐的反应分别得到内加合物23和24。加合物23具有合适的立体化学和官能团，用于合成丙戊烷和相关的二萜。

  DOI：

  10.1016/0040-4020(78)80096-9

文献信息

• Bicyclo[3.1.0]hex-(1,5)-ene and bicyclo[4.1.0]hept-(1,6)-ene
  作者：Kenneth B. Wiberg、George Bonneville

  DOI：10.1016/0040-4039(82)80136-6

  日期：1982.1

  The formation and trapping of bicyclo[3.1.0]hex-(1,5)-ene and bicyclo[4.1.0]hept-(1,6)-ene from the corresponding vicinal dibromides is described.

  描述了由相应的邻位二溴化物形成和捕获双环[3.1.0] hex-（1,5）-烯和双环[4.1.0]庚基-（1,6）-烯。
• Attempted Synthesis of Tricyclo[3.3.2.0²⁴]DEC-2(4)-ENE
  作者：Philip J. Chenier、Michael J. Bauer、Dale A. Southard

  DOI：10.1080/00397919608003729

  日期：1996.3

  Abstract The synthesis of tricyclo[3.3.2.02,4]-dec-2(4)-ene (3) has been attempted using a route analogous to those previously developed for 1 and 2. Complications were encountered in the synthesis. The conformational problems of the larger polycyclic structures in the synthesis of 3 must be more difficult to overcome than the increased angle strain of the smaller rings when 1 or 2 are synthesized

  摘要 三环[3.3.2.02,4]-dec-2(4)-ene (3) 的合成已尝试使用与先前为 1 和 2 开发的路线类似的路线。合成过程中遇到了复杂情况。与合成 1 或 2 时较小环的角应变增加相比，3 合成中较大多环结构的构象问题必须更难以​​克服。
• Cycloheptatrien-1, 6-dicarbonsäure und Bicyclo-[4, 1, 0]-2, 4-heptadien-1, 6-dicarbonsäureanhydrid
  作者：R. Darms、T. Threlfall、M. Pesaro、A. Eschenmoser

  DOI：10.1002/hlca.19630460746

  日期：——

  The synthesis and some of the properties of cycloheptatriene-1,6-dicarboxylic acid and its norcaradieneoid anhydride are describe.

  描述了环庚三烯-1,6-二羧酸及其降冰片烯类酸酐的合成及其一些性能。
• 1,2-Bridged cyclopropenes
  作者：Kenneth B. Wiberg、Dean R. Artis、G. Bonneville

  DOI：10.1021/ja00021a024

  日期：1991.10

  The dehalogenations of 1,5-dihalobicyclo[3.1.0]hexanes and 1,6-dihalobicyclo[4.1.0]heptanes have been studied in solution and in the gas phase. The solution reactions led to the formation of bicyclo[3.1.0]hex-1(5)-ene and bicyclo[4.1.0]hept-1(6)-ene, respectively, but this was followed by rapid ene reactions forming dimers, which then coupled to form tetramers. The cyclopropenes could be trapped as Diels-Alder adducts. In the gas phase, with use of either potassium atoms or solid methyllithium, the products of thermal ring opening, methylenecyclopentene and methylenecyclohexene, were formed. A set of theoretical calculations was carried out dealing with the strain energies, inversion barriers, bond properties, and atom properties of bicyclo[1.1.0]but-1(3)-ene, bicyclo[2.1.0]pent-1(4)-ene, and the cyclopropenes from the experimental study. Whereas bicyclohexene and bicycloheptene appear to be fairly normal compounds except for their high strain energies, bicyclopentene may be a transition state for the carbon scrambling of methylenecyclobutylidene, and bicyclobutene has an unusual structure and charge-density distribution.
• Synthesis and chemistry of some tricyclic cyclopropenes. 3. Tricyclo[3.2.1.02,4]oct-2(4)-ene
  作者：Philip J. Chenier、Michael J. Bauer、Christina L. Hodge

  DOI：10.1021/jo00048a032

  日期：1992.10

  The title compound cyclopropene 2 has been synthesized in situ from dibromide 8 and diiodide 9 via dehalogenation of tert-butyllithium in THF at -78-degrees-C. The dihalides were formed in six steps starting with cyclopentadiene and (chloromethyl)maleic anhydride. In the presence of diphenylisobenzofuran (DPIBF) 2 forms a Diels-Alder adduct, most probably 10. Cyclopropene 2 and a previously synthesized cyclopropene 1 were decomposed under these same conditions, only without DPIBF present, to give complex mixtures of products, some of which were characterized as tert-butyl adducts and dimers via the ene reaction of the cyclopropenes.