2-{4-[1,1,2-Trifluoro-2-(1,1,2,3,3,3-hexafluoro-2-heptafluoropropyloxy-propoxy)-ethoxy]-phenyl}-4,5-dihydro-oxazole | 144373-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-{4-[1,1,2-Trifluoro-2-(1,1,2,3,3,3-hexafluoro-2-heptafluoropropyloxy-propoxy)-ethoxy]-phenyl}-4,5-dihydro-oxazole
• 英文别名: 2-[4-[1,1,2-Trifluoro-2-[1,1,2,3,3,3-hexafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propoxy]ethoxy]phenyl]-4,5-dihydro-1,3-oxazole
• CAS: 144373-63-7
• 化学式: C₁₇H₉F₁₆NO₄
• 分子量: 595.237
• InChiKey: PWOLALVYVHBHPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  49.3
• 氢给体数：
  0
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  4-(4,5-二氢-2-噁唑)苯酚 、 2-全氟丙氧基全氟丙基三氟乙烯基醚 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以81%的产率得到2-{4-[1,1,2-Trifluoro-2-(1,1,2,3,3,3-hexafluoro-2-heptafluoropropyloxy-propoxy)-ethoxy]-phenyl}-4,5-dihydro-oxazole
  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.