perfluoro(3,4-epoxyoxolane) | 680615-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: perfluoro(3,4-epoxyoxolane)
• 英文别名: 3,6-Dioxabicyclo[3.1.0]hexane, 1,2,2,4,4,5-hexafluoro-；1,2,2,4,4,5-hexafluoro-3,6-dioxabicyclo[3.1.0]hexane
• CAS: 680615-57-0
• 化学式: C₄F₆O₂
• 分子量: 194.033
• InChiKey: LEEJBGRIMQGMBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  硫脲 、 perfluoro(3,4-epoxyoxolane) 以 甲醇 为溶剂， 反应 1.0h， 以68%的产率得到2-amino-4,4,6,6,6a-pentafluoro-3a-hydroxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]thiazole
  参考文献：
  名称：

  Perfluoroepoxyoxolanes in the synthesis of fluorine-containing heterocycles

  摘要：

  Perfluoro-3,4-epoxyoxolane and 3,4-epoxy-2-trifluoromethylpentafluorooxolane readily reacted with difunctional nucleophiles via opening of the oxirane ring and subsequent heterocyclization. Their reactions with thiourea and o-phenylenediamine gave new fluorine-containing fused heterocyclic compounds, 2-amino-3a-hydroxy-4,4,6,6,6a-pentafluoro-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]thiazole and 1,1,3,3-tetrafluoro- and 1-trifluoromethyl-1,3,3-trifluoro-1,3-dihydrofuro[3,4-b]quinoxalines, respectively. The molecular and crystalline structures of the products were determined by X-ray analysis.

  DOI：

  10.1134/s1070428009060141
• 作为产物：
  描述：

  六氟-2,5-二氢呋喃 在 sodium hypochlorite 、 水 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以60%的产率得到perfluoro(3,4-epoxyoxolane)
  参考文献：
  名称：

  Synthesis of Perfluoro- and 2-Trifluoromethylpentafluorodihydrofurans and Their Epoxy Derivatives

  摘要：

  Perfluorotetrahydrofuran-2-carboxylic acid was converted through a series of transformations into perfluoro-2,3-dihydrofuran and perfluoro-2,5-dihydrofuran; likewise, from (2-perfluorotetrahydrofuryl)difluoroacetic acid 2-trifluoromethylpentafluoro-2,3-dihydrofuran was obtained. Perfluoro-2,3-dihydrofuran and 2-trifluoromethylpentafluoro-2,3-dihydrofuran underwent isomerization into perfluoro-2,5-dihydrofuran and 2-trifluoromethylpentafluoro-2,5-dihydrofuran by the action of cesium fluoride. Treatment of perfluoro-2,5-dihydrofuran with SbF5 resulted in ring opening and formation of cis-perfluoro-2-butenoyl fluoride, while 2-trifluoromethylpentafluoro-2,3-dihydrofuran was converted into 2-trifluoromethylpentafluoro-2,5-dihydrofuran under the same conditions. Perfluoro-3,4-epoxytetrahydrofuran and 2-trifluoromethyl-3,4-epoxypenta-fluorotetrahydrofuran containing fused oxirane and tetrahydrofuran rings were synthesized by reactions of perfluoro-2,5-dihydrofuran and 2-trifluoromethylpentafluoro-2,5-dihydrofuran, respectively, with sodium hypochlorite.

  DOI：

  10.1023/b:rujo.0000003194.13428.68

文献信息

• Synthesis of Perfluoro- and 2-Trifluoromethylpentafluorodihydrofurans and Their Epoxy Derivatives
  作者：T. I. Filyakova、M. I. Kodess、A. Ya. Zapevalov、V. I. Saloutin

  DOI：10.1023/b:rujo.0000003194.13428.68

  日期：2003.7

  Perfluorotetrahydrofuran-2-carboxylic acid was converted through a series of transformations into perfluoro-2,3-dihydrofuran and perfluoro-2,5-dihydrofuran; likewise, from (2-perfluorotetrahydrofuryl)difluoroacetic acid 2-trifluoromethylpentafluoro-2,3-dihydrofuran was obtained. Perfluoro-2,3-dihydrofuran and 2-trifluoromethylpentafluoro-2,3-dihydrofuran underwent isomerization into perfluoro-2,5-dihydrofuran and 2-trifluoromethylpentafluoro-2,5-dihydrofuran by the action of cesium fluoride. Treatment of perfluoro-2,5-dihydrofuran with SbF5 resulted in ring opening and formation of cis-perfluoro-2-butenoyl fluoride, while 2-trifluoromethylpentafluoro-2,3-dihydrofuran was converted into 2-trifluoromethylpentafluoro-2,5-dihydrofuran under the same conditions. Perfluoro-3,4-epoxytetrahydrofuran and 2-trifluoromethyl-3,4-epoxypenta-fluorotetrahydrofuran containing fused oxirane and tetrahydrofuran rings were synthesized by reactions of perfluoro-2,5-dihydrofuran and 2-trifluoromethylpentafluoro-2,5-dihydrofuran, respectively, with sodium hypochlorite.
• Perfluoroepoxyoxolanes in the synthesis of fluorine-containing heterocycles
  作者：T. I. Filyakova、A. Ya. Zapevalov、M. I. Kodess、P. A. Slepukhin、V. I. Saloutin

  DOI：10.1134/s1070428009060141

  日期：2009.6

  Perfluoro-3,4-epoxyoxolane and 3,4-epoxy-2-trifluoromethylpentafluorooxolane readily reacted with difunctional nucleophiles via opening of the oxirane ring and subsequent heterocyclization. Their reactions with thiourea and o-phenylenediamine gave new fluorine-containing fused heterocyclic compounds, 2-amino-3a-hydroxy-4,4,6,6,6a-pentafluoro-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]thiazole and 1,1,3,3-tetrafluoro- and 1-trifluoromethyl-1,3,3-trifluoro-1,3-dihydrofuro[3,4-b]quinoxalines, respectively. The molecular and crystalline structures of the products were determined by X-ray analysis.