(R,E)-1-chloro-4-(5-phenyl-2-(phenylsulfonyl)pent-4-en-2-yl)benzene | 1241668-15-4

• 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: (R,E)-1-chloro-4-(5-phenyl-2-(phenylsulfonyl)pent-4-en-2-yl)benzene
• CAS: 1241668-15-4
• 化学式: C₂₃H₂₁ClO₂S
• 分子量: 396.938
• InChiKey: LQEQIAPUDFIZLW-OXHGWOFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  cinnamyl 2-(4-chlorophenyl)-2-(phenylsulfonyl)propanoate 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 生成 1-chloro-4-((S)-3-phenyl-2-(phenylsulfonyl)pent-4-en-2-yl)benzene 、 1-chloro-4-((R)-3-phenyl-2-(phenylsulfonyl)pent-4-en-2-yl)benzene 、 (R,E)-1-chloro-4-(5-phenyl-2-(phenylsulfonyl)pent-4-en-2-yl)benzene 、 (S,E)-1-chloro-4-(5-phenyl-2-(phenylsulfonyl)pent-4-en-2-yl)benzene
  参考文献：
  名称：

  Stereospecific Decarboxylative Allylation of Sulfones

  摘要：

  Allyl sulfonylacetic esters undergo highly stereospecific, palladium-catalyzed decarboxylative allylation. The reaction allows the stereospecific formation of tertiary homoallylic sulfones in high yield. In contrast to related reactions that proceed at -100 degrees C and require highly basic preformed organometallics, the decarboxylative coupling described herein occurs under mild nonbasic conditions and requires no stoichiometric additives. Allylation of the intermediate a-sulfonyl anion is more rapid than racemization, leading to a highly enantiospecific process. Density functional theory calculations indicate that the barrier for racemization is 9.9 kcal/mol, so the barrier for allylation must be <9.9 kcal/mol.

  DOI：

  10.1021/ja104196x