3-(1-chloro-2,2,2-trifluoroethanesulfonyl)propene | 881901-13-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 磺酰卤
• 英文名称: 3-(1-chloro-2,2,2-trifluoroethanesulfonyl)propene
• 英文别名: 3-(1-chloro-2,2,2-trifluoroethyl)sulfonylprop-1-ene
• CAS: 881901-13-9
• 化学式: C₅H₆ClF₃O₂S
• 分子量: 222.616
• InChiKey: FXCZOWVDEXCZJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(1-chloro-2,2,2-trifluoroethanesulfonyl)propene 在 氯 、 三乙胺 作用下， 以 四氯化碳 、 乙醚 为溶剂， 反应 1.25h， 生成 2-chloro-3-(1-chloro-2,2,2-trifluoroethanesulfonyl)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
• 作为产物：
  描述：

  sodium 1-chloro-2,2,2-trifluoroethanesulfinate 、 3-溴丙烯 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以74.5%的产率得到3-(1-chloro-2,2,2-trifluoroethanesulfonyl)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