3-(3-chloroprop-2-ynyloxy)prop-1-ene | 1300035-16-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3-chloroprop-2-ynyloxy)prop-1-ene
• CAS: 1300035-16-8
• 化学式: C₆H₇ClO
• 分子量: 130.574
• InChiKey: RKBXTHKLTDGYJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  8.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-(3-chloroprop-2-ynyloxy)prop-1-ene 在 di(rhodium)tetracarbonyl dichloride 作用下， 以 对二甲苯 为溶剂， 以74%的产率得到6-chloro-3a,4-dihydro-1H-cyclopenta[c]furan-5(3H)-one
  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：

  allyl propargyl ether 在 四氯化碳 、 四丁基氟化铵 、 caesium carbonate 作用下， 生成 3-(3-chloroprop-2-ynyloxy)prop-1-ene
  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