[2S,3aR,(S)S]-5-oxo-3a-phenyl-2-[2-(p-tolylsulfinyl)phenyl]-1,2,3,3a,4,5-hexahydropentalene-2-carbonitrile | 1392204-14-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [2S,3aR,(S)S]-5-oxo-3a-phenyl-2-[2-(p-tolylsulfinyl)phenyl]-1,2,3,3a,4,5-hexahydropentalene-2-carbonitrile
• 英文别名: (2S,3aR)-2-[2-[(S)-(4-methylphenyl)sulfinyl]phenyl]-5-oxo-3a-phenyl-3,4-dihydro-1H-pentalene-2-carbonitrile
• CAS: 1392204-14-6
• 化学式: C₂₈H₂₃NO₂S
• 分子量: 437.562
• InChiKey: ILDXOMPKJIRKQP-AUSNRZEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  77.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [(S)S]-4-phenyl-2-(prop-2-ynyl)-2-[2-(p-tolylsulfinyl)phenyl]pent-4-enenitrile 在 dicobalt octacarbonyl 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 13.5h， 以56%的产率得到[2S,3aR,(S)S]-5-oxo-3a-phenyl-2-[2-(p-tolylsulfinyl)phenyl]-1,2,3,3a,4,5-hexahydropentalene-2-carbonitrile
  参考文献：
  名称：

  Asymmetric Intramolecular Pauson–Khand Reaction Mediated by a Remote Sulfenyl or Sulfinyl Group

  摘要：

  In this work, we report the use of the asymmetric intramolecular Pauson-Khand reactions of 4-aryl-4-cyano-1,6-enynes for obtaining enantiomerically enriched bicyclo[3.3.0]octenones, and the influence of both the quaternary stereocenter and the sulfur functions located at ortho-position of the aryl group, on their stereoselectivity and reactivity. The sulfenyl derivatives bearing substituted or unsubstituted triple bonds and mono- and disubstituted alkene moieties afford bicyclo[3,3,0]octenones in high yields with complete diastereocontrol. These results are explained by assuming the association of the lone electron pair at sulfur to the Co-alkyne complexes.

  DOI：

  10.1021/jo3011039