Methyl 2,2,3,3-tetrafluoro-3-[1,1,1,2,3,3-hexafluoro-3-(1,2,2-trifluoro-2-phenoxyethoxy)propan-2-yl]oxypropanoate | 144373-64-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Methyl 2,2,3,3-tetrafluoro-3-[1,1,1,2,3,3-hexafluoro-3-(1,2,2-trifluoro-2-phenoxyethoxy)propan-2-yl]oxypropanoate
• CAS: 144373-64-8
• 化学式: C₁₅H₉F₁₃O₅
• 分子量: 516.213
• InChiKey: MOQIFBAPAGBUAC-UHFFFAOYSA-N

物化性质

• 沸点：
  398.9±42.0 °C(Predicted)
• 密度：
  1.549±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  甲基全氟(5-甲基-4,7-二氧环己烷-8-烯酸乙酯) 、 苯酚 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以72%的产率得到Methyl 2,2,3,3-tetrafluoro-3-[1,1,1,2,3,3-hexafluoro-3-(1,2,2-trifluoro-2-phenoxyethoxy)propan-2-yl]oxypropanoate
  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.