N-(1-(benzyloxy)but-3-en-2-yl)-N-(3-chloroprop-2-ynyl)-4-methylbenzenesulfonamide | 1300035-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(1-(benzyloxy)but-3-en-2-yl)-N-(3-chloroprop-2-ynyl)-4-methylbenzenesulfonamide
• 英文别名: N-(3-chloroprop-2-ynyl)-4-methyl-N-(1-phenylmethoxybut-3-en-2-yl)benzenesulfonamide
• CAS: 1300035-26-0
• 化学式: C₂₁H₂₂ClNO₃S
• 分子量: 403.93
• InChiKey: CMTZKKKQKLDYCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(1-(benzyloxy)but-3-en-2-yl)-N-(3-chloroprop-2-ynyl)-4-methylbenzenesulfonamide 在 di(rhodium)tetracarbonyl dichloride 作用下， 以 对二甲苯 为溶剂， 以73%的产率得到(3S,3aS)-6-chloro-2-(4-methylphenyl)sulfonyl-3-(phenylmethoxymethyl)-1,3,3a,4-tetrahydrocyclopenta[c]pyrrol-5-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：

  在 四氯化碳 、 四丁基氟化铵 、 caesium carbonate 作用下， 生成 N-(1-(benzyloxy)but-3-en-2-yl)-N-(3-chloroprop-2-ynyl)-4-methylbenzenesulfonamide
  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