(+/-)-2-(prop-2-ynyl)-2-[2-(p-tolylsulfenyl)phenyl]pent-4-enenitrile | 1392204-34-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (+/-)-2-(prop-2-ynyl)-2-[2-(p-tolylsulfenyl)phenyl]pent-4-enenitrile
• 英文别名: 2-[2-(4-Methylphenyl)sulfanylphenyl]-2-prop-2-ynylpent-4-enenitrile
• CAS: 1392204-34-0
• 化学式: C₂₁H₁₉NS
• 分子量: 317.455
• InChiKey: HAGBRXDGFXXFFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-2-(prop-2-ynyl)-2-[2-(p-tolylsulfenyl)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 1.58h， 以68%的产率得到5-oxo-2-[2-(p-tolylsulfenyl)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
• 作为产物：
  描述：

  2-碘苯基乙腈 在 铜 、 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 19.17h， 生成 (+/-)-2-(prop-2-ynyl)-2-[2-(p-tolylsulfenyl)phenyl]pent-4-enenitrile
  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

文献信息

• Asymmetric Intramolecular Pauson–Khand Reaction Mediated by a Remote Sulfenyl or Sulfinyl Group
  作者：José Luis García Ruano、Esther Torrente、Alejandro Parra、José Alemán、Ana M. Martín-Castro

  DOI：10.1021/jo3011039

  日期：2012.8.3

  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.