3,3,4,4,5,5-hexafluoro-1,2-dioxolane | 5930-64-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 3,3,4,4,5,5-hexafluoro-1,2-dioxolane
• 英文别名: Hexafluoro-1,2-dioxolane；3,3,4,4,5,5-hexafluorodioxolane
• CAS: 5930-64-3
• 化学式: C₃F₆O₂
• 分子量: 182.022
• InChiKey: YJLWQZAVDVLARD-UHFFFAOYSA-N

物化性质

• 沸点：
  -22.0±40.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  二氟丙二酰氟 在 fluorine 、 cesium fluoride 作用下， 以70%的产率得到3,3,4,4,5,5-hexafluoro-1,2-dioxolane
  参考文献：
  名称：

  Perfluoro-1,2-dioxolane. A new synthesis and its gas-phase structure

  摘要：

  Highly pure perfluoro-1,2-dioxolane was prepared in good yields by fluorination of 2,2-difluoropropanedioyl difluoride with elemental fluorine in the presence of CsF. A gas-phase electron diffraction study results for the five-membered ring in a half-chair conformation possessing C2 symmetry and the following geometric parameters (r(a) distances and angle(alpha) angles, error limits are 3sigma values and refer to the last digit): O-O = 144.3(11) pm, O-C = 137.7(15) pm, C-C = 153.1(5) pm, (C-F)mean = 131.8(4) pm, CCC = 98.1(13)-degrees, CCO = 107.3(12)-degrees, COO = 102.9(9)-degrees, FCF = 109.8(9)-degrees and the torsional angle around the O-O bond tau(CO-OC) = 48(2)-degrees. Ab initio calculations (HF/4-21G and HF/4-21G*) confirm that this half-chair conformation is the only stable structure along the pseudorotational path and they reproduce the geometric parameters reasonably well.

  DOI：

  10.1016/0022-2860(92)80155-b

文献信息

• Perfluoro-1,2-dioxolane. A new synthesis and its gas-phase structure
  作者：Anding Jin、Hans-Georg Mack、Alfred Waterfeld、Marwan Dakkouri、Heinz Oberhammer

  DOI：10.1016/0022-2860(92)80155-b

  日期：1992.11

  Highly pure perfluoro-1,2-dioxolane was prepared in good yields by fluorination of 2,2-difluoropropanedioyl difluoride with elemental fluorine in the presence of CsF. A gas-phase electron diffraction study results for the five-membered ring in a half-chair conformation possessing C2 symmetry and the following geometric parameters (r(a) distances and angle(alpha) angles, error limits are 3sigma values and refer to the last digit): O-O = 144.3(11) pm, O-C = 137.7(15) pm, C-C = 153.1(5) pm, (C-F)mean = 131.8(4) pm, CCC = 98.1(13)-degrees, CCO = 107.3(12)-degrees, COO = 102.9(9)-degrees, FCF = 109.8(9)-degrees and the torsional angle around the O-O bond tau(CO-OC) = 48(2)-degrees. Ab initio calculations (HF/4-21G and HF/4-21G*) confirm that this half-chair conformation is the only stable structure along the pseudorotational path and they reproduce the geometric parameters reasonably well.