[2-Chloro-1,1,2-trifluoro-2-[1,1,2,3,3,3-hexafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propoxy]ethoxy]benzene | 144373-68-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [2-Chloro-1,1,2-trifluoro-2-[1,1,2,3,3,3-hexafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propoxy]ethoxy]benzene
• CAS: 144373-68-2
• 化学式: C₁₄H₅ClF₁₆O₃
• 分子量: 560.619
• InChiKey: DTVRBRJUGMDTEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  2-全氟丙氧基全氟丙基三氟乙烯基醚 、 3-硝基苯酚钠盐 在 六氯乙烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到[2-Chloro-1,1,2-trifluoro-2-[1,1,2,3,3,3-hexafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propoxy]ethoxy]benzene
  参考文献：
  名称：

  Addition of phenols to perfluorovinyl ethers. Protonation and halogenation of carbanionic intermediates

  摘要：

  Fluorinated ethers ArOCF2CFHORf are obtained in good yield by base-catalyzed addition of phenols to perfluoroalkyl vinyl ethers, CF2=CFORf (Rf = C3F7, C3F7OCF(CF3)CF2, CH3O2CCF2CF2OCF(CF3)CF2). Reaction of sodium phenoxides with fluorinated vinyl ethers and hexachloroethane affords chlorinated ethers ArOCF2CFClORf. Treatment of BrCF2CFBrOC3F, with sodium phenoxide in the presence of CF2=CFOC3F7 gives PhOCF2CFBrOC3F7 in high yield at room temperature, probably by an anionic chain mechanism. Sodium phenoxide reacts cleanly with CF2=CFOC3F7 in the absence of an electrophile to give a 1:1 cis-trans mixture of olefins PhOCF=CFOC3F7. NMR chemical shifts of the OCF2CFHORf group proton shows an unusually large solvent dependence.

  DOI：

  10.1021/jo00052a008

文献信息

• Addition of phenols to perfluorovinyl ethers. Protonation and halogenation of carbanionic intermediates
  作者：Andrew E. Feiring、Edward R. Wonchoba

  DOI：10.1021/jo00052a008

  日期：1992.12

  Fluorinated ethers ArOCF2CFHORf are obtained in good yield by base-catalyzed addition of phenols to perfluoroalkyl vinyl ethers, CF2=CFORf (Rf = C3F7, C3F7OCF(CF3)CF2, CH3O2CCF2CF2OCF(CF3)CF2). Reaction of sodium phenoxides with fluorinated vinyl ethers and hexachloroethane affords chlorinated ethers ArOCF2CFClORf. Treatment of BrCF2CFBrOC3F, with sodium phenoxide in the presence of CF2=CFOC3F7 gives PhOCF2CFBrOC3F7 in high yield at room temperature, probably by an anionic chain mechanism. Sodium phenoxide reacts cleanly with CF2=CFOC3F7 in the absence of an electrophile to give a 1:1 cis-trans mixture of olefins PhOCF=CFOC3F7. NMR chemical shifts of the OCF2CFHORf group proton shows an unusually large solvent dependence.