(E)-1-(tridecafluorohexane-1-sulfonyl)-propene | 881901-11-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: (E)-1-(tridecafluorohexane-1-sulfonyl)-propene
• 英文别名: 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-6-[(E)-prop-1-enyl]sulfonylhexane
• CAS: 881901-11-7
• 化学式: C₉H₅F₁₃O₂S
• 分子量: 424.183
• InChiKey: UKZZLEPPYUSANN-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (E)-1-(tridecafluorohexane-1-sulfonyl)-propene 、 2,3-二甲基-1,3-丁二烯 反应 120.0h， 以93%的产率得到1,2,4-trimethyl-5-(tridecafluorohexane-1-sulfonyl)cyclohexene
  参考文献：
  名称：

  An easy preparation of per- and poly-fluoroalkyl propenyl sulfones

  摘要：

  Sodium tridecafluorohexanesulfinate (1a) and sodium 1-chloro-2,2,2-trifluoroethanesulfinate (1b) were prepared by the treatment of 1-iodo-tridecafluorohexane and 1-bromo-1-chloro-2,2,2-trifluoroethane with sodium dithionite in a water-acetonitrile solution. Prolonged reaction of 1a with allyl bromide in DMF afforded tridecafluorohexane 1-propenyl sulfone 2 as the only product in good yield. A similar treatment of 1b gave exclusively 1-chloro-2,2,2-trifluoroethane 3-propenylsulfone 4. Bromination of 4 followed by dehydrobromination with Et3N resulted in a mixture of 1-chloro-2,2,2-trifluoroethane 3-bromo-1-propenyl sulfone 6 and 1-chloro-2,2,2-trifluoroethane 2-bromo-3-propenyl sulfone 7, while dehydrobromination with pyridine gave sulfone 6 practically as the only product. alpha,beta-Unsaturated sulfones 2 and 6 were shown to be active dienophiles. (C) 2005 Elsevier B.V All lights reserved.

  DOI：

  10.1016/j.jfluchem.2005.02.014
• 作为产物：
  描述：

  全氟己基碘烷 在 sodium dithionite 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 261.0h， 生成 (E)-1-(tridecafluorohexane-1-sulfonyl)-propene
  参考文献：
  名称：

  An easy preparation of per- and poly-fluoroalkyl propenyl sulfones

  摘要：

  Sodium tridecafluorohexanesulfinate (1a) and sodium 1-chloro-2,2,2-trifluoroethanesulfinate (1b) were prepared by the treatment of 1-iodo-tridecafluorohexane and 1-bromo-1-chloro-2,2,2-trifluoroethane with sodium dithionite in a water-acetonitrile solution. Prolonged reaction of 1a with allyl bromide in DMF afforded tridecafluorohexane 1-propenyl sulfone 2 as the only product in good yield. A similar treatment of 1b gave exclusively 1-chloro-2,2,2-trifluoroethane 3-propenylsulfone 4. Bromination of 4 followed by dehydrobromination with Et3N resulted in a mixture of 1-chloro-2,2,2-trifluoroethane 3-bromo-1-propenyl sulfone 6 and 1-chloro-2,2,2-trifluoroethane 2-bromo-3-propenyl sulfone 7, while dehydrobromination with pyridine gave sulfone 6 practically as the only product. alpha,beta-Unsaturated sulfones 2 and 6 were shown to be active dienophiles. (C) 2005 Elsevier B.V All lights reserved.

  DOI：

  10.1016/j.jfluchem.2005.02.014

文献信息

• An easy preparation of per- and poly-fluoroalkyl propenyl sulfones
  作者：Wojciech Dmowski、Krystyna Piasecka-Maciejewska

  DOI：10.1016/j.jfluchem.2005.02.014

  日期：2005.6

  Sodium tridecafluorohexanesulfinate (1a) and sodium 1-chloro-2,2,2-trifluoroethanesulfinate (1b) were prepared by the treatment of 1-iodo-tridecafluorohexane and 1-bromo-1-chloro-2,2,2-trifluoroethane with sodium dithionite in a water-acetonitrile solution. Prolonged reaction of 1a with allyl bromide in DMF afforded tridecafluorohexane 1-propenyl sulfone 2 as the only product in good yield. A similar treatment of 1b gave exclusively 1-chloro-2,2,2-trifluoroethane 3-propenylsulfone 4. Bromination of 4 followed by dehydrobromination with Et3N resulted in a mixture of 1-chloro-2,2,2-trifluoroethane 3-bromo-1-propenyl sulfone 6 and 1-chloro-2,2,2-trifluoroethane 2-bromo-3-propenyl sulfone 7, while dehydrobromination with pyridine gave sulfone 6 practically as the only product. alpha,beta-Unsaturated sulfones 2 and 6 were shown to be active dienophiles. (C) 2005 Elsevier B.V All lights reserved.