dimethyl 2-allyl-2-(3-chloroprop-2-ynyl)malonate | 1300035-20-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl 2-allyl-2-(3-chloroprop-2-ynyl)malonate
• CAS: 1300035-20-4
• 化学式: C₁₁H₁₃ClO₄
• 分子量: 244.675
• InChiKey: UAPWJKCAVQJZNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  dimethyl 2-allyl-2-(3-chloroprop-2-ynyl)malonate 在 di(rhodium)tetracarbonyl dichloride 作用下， 以 对二甲苯 为溶剂， 以74%的产率得到dimethyl 6-chloro-5-oxo-3,3a,4,5-tetrahydropentalene-2,2(1H)-dicarboxylate
  参考文献：
  名称：

  Computationally Designed and Experimentally Confirmed Diastereoselective Rhodium-Catalyzed Pauson−Khand Reaction at Room Temperature

  摘要：

  The computational analysis of the rhodium-catalyzed Pauson-Khand reaction indicates that the key transition state is highly charge-polarized, wherein different diastereoisomers have distinctively different charge polarization patterns. Experimental studies demonstrate that chloro-enynes provide the optimal sigma-electron-withdrawing group to promote polarization and thereby reduce the activation barrier to provide a highly diastereoselective reaction at room temperature.

  DOI：

  10.1021/ja107895g
• 作为产物：
  描述：

  2-烯丙基-2-(2-丙炔-1-基)丙二酸二甲酯 在 四氯化碳 、 四丁基氟化铵 、 caesium carbonate 作用下， 生成 dimethyl 2-allyl-2-(3-chloroprop-2-ynyl)malonate
  参考文献：
  名称：

  Computationally Designed and Experimentally Confirmed Diastereoselective Rhodium-Catalyzed Pauson−Khand Reaction at Room Temperature

  摘要：

  The computational analysis of the rhodium-catalyzed Pauson-Khand reaction indicates that the key transition state is highly charge-polarized, wherein different diastereoisomers have distinctively different charge polarization patterns. Experimental studies demonstrate that chloro-enynes provide the optimal sigma-electron-withdrawing group to promote polarization and thereby reduce the activation barrier to provide a highly diastereoselective reaction at room temperature.

  DOI：

  10.1021/ja107895g