trifluoromethanesulfonic acid 2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethyloxy)ethoxy]ethyl ester | 1202023-73-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: trifluoromethanesulfonic acid 2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethyloxy)ethoxy]ethyl ester
• 英文别名: [2,2-Difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethyl] trifluoromethanesulfonate
• CAS: 1202023-73-1
• 化学式: C₆H₂F₁₂O₅S
• 分子量: 414.126
• InChiKey: HQTOLWOHIPYZRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  trifluoromethanesulfonic acid 2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethyloxy)ethoxy]ethyl ester 以 乙腈 为溶剂， 反应 10.0h， 生成 3-(2,2-difluoro-2-(1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy)ethyl)-1-(2,3,3,3-tetrafluoro-2-(1,1,2,3,3,3-hexafluoro-2-(perfluoropropoxy)propoxy)propyl)-1H-imidazol-3-ium 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
  参考文献：
  名称：

  Ag Complexes of NHC Ligands Bearing Polyfluoroalkyl and/or Polyfluoropolyalkoxy Ponytails. Why Are Polyethers More Fluorous Than Alkyls?

  摘要：

  A series of fluorous silver complexes bearing two fluorous NHC ligands was synthesized from bis(polyfluoroallcylated) or bis(polyfluoropolyoxaalkylated) imidazolium salts and silver oxide in acetonitrile. The starting salts were prepared either under conventional conditions in two steps via polyfluoroalkylated imidazoles or preferably directly from imidazole and the respective polyfluoroalkyl triflates or polyfluoropolyoxaalkyl nonaflates bearing a nonfluorinated ethylene or methylene spacer. Surprisingly, striking differences in fluorophilicity were observed for both starting imidazolium salts and target Ag-NHC complexes depending on the type of polyfluorinated chains. While the complexes bearing a polyfluoroalkyl ponytail displayed moderate fluorophilicities f(i), in the range of 0.9-1.8, the presence of fluorinated polyether chains resulted in much higher fluorophilicity reaching for unbranched polyethers values as high as 3.2 with excellent solubility in perfluorinated solvents. For the explanation, DFT calculations on the model imidazolium salts showed that, in contrast to polyfluoroalkyl ponytails pointing out of the imidazolium rings, dominant conformation of the polyfluoropolyether chain is able to shield fluorophobic counteranions against the perfluorinated environment, minimizing thus fluorophobic interactions. We also employed DFT calculations for the confirmation of the higher flexibility of perfluoropolyether chains compared with perfluoroalkyl chains, scanning the energy content of two model compounds, perfluorohexane and perfluoro-3-oxahexane, on their C3-C4 or O-C3 torsion angle.

  DOI：

  10.1021/om201062c
• 作为产物：
  描述：

  1H,1H-九氟-3,6-二噁-1-庚醇 、 三氟甲磺酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 25.33h， 以80%的产率得到trifluoromethanesulfonic acid 2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethyloxy)ethoxy]ethyl ester
  参考文献：
  名称：

  2,2,6,6-四氟-4-苯基甲基吗啉-3-酮的合成：氟化三乙二醇的一种简单方法

  摘要：

  2,2,6,6-四氟-4-苯基甲基吗啉-3-酮是通过一个新的制备步骤，通过使包含聚-CF 2 O-基团的三甘醇二（三氟甲磺酸盐）与苄胺反应而制得的。三氟甲基磺酸盐和三氟甲氧基衍生物与苄胺的反应得到亲核取代的产物或由二氟甲氧基的碱性水解得到的产物。通过三氟甲磺酸氟代烷基二烷基酯和苄基胺的组合，用氟代烷烃取代氟醚链产生了氟化的苯基甲基哌啶和苯基甲基a庚因。

  DOI：

  10.1016/j.jfluchem.2009.05.014