2-chloro-2-chloromethyl-succinic acid anhydride | 69698-79-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-chloro-2-chloromethyl-succinic acid anhydride
• 英文别名: 3-Chloro-3-(chloromethyl)oxolane-2,5-dione；3-chloro-3-(chloromethyl)oxolane-2,5-dione
• CAS: 69698-79-9
• 化学式: C₅H₄Cl₂O₃
• 分子量: 182.991
• InChiKey: LEPWDYJRPKCVEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  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
• 作为产物：
  描述：

  衣康酸酐 在 氯 作用下， 以 四氯化碳 为溶剂， 生成 2-chloro-2-chloromethyl-succinic acid anhydride
  参考文献：
  名称：

  1,2-Bridged cyclopropenes

  摘要：

  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.

  DOI：

  10.1021/ja00021a024

文献信息

• 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.
• Diels-alder reactions of substituted maleic anhydrides with 1-vinylcoclohexane
  作者：Takashi Tokoroyama、Keizo Matsuo、Takashi Kubota

  DOI：10.1016/0040-4020(78)80096-9

  日期：1978.1

  The Diels-Alder reaction of 1-vinylcyclohexene with aconitic anhydride gives the adduct 5b which has the reversed stereochemistry of that predicted by Alder's endo rule. On the other hand, reactions with chloromethylmaleic anhydride and citraconic anhydride afford endo-adducts 23 and 24, respectively. Adduct 23 has the appropriate stereochemistry and functionality for the syntheses of clerodane and

  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。