六氟-2,5-二氢呋喃 | 24849-02-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 中文名称: 六氟-2,5-二氢呋喃
• 英文名称: perfluoro-2,5-dihydrofuran
• 英文别名: Hexafluoro-2,5-dihydrofuran；2,2,3,4,5,5-hexafluorofuran
• CAS: 24849-02-3
• 化学式: C₄F₆O
• 分子量: 178.034
• InChiKey: SWAZOEMXQGHIIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  六氟-2,5-二氢呋喃 在 溴 作用下， 反应 12.0h， 以92%的产率得到3,4-dibromohexafluorotetrahydrofuran
  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
• 作为产物：
  描述：

  potassium perfluorotetrahydrofuran-2-carboxylate 在 potassium carbonate 、 cesium fluoride 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 2.0h， 以91%的产率得到六氟-2,5-二氢呋喃
  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

• Process for the preparation of difluoromaleic anhydride
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US05112993A1

  公开（公告）日：1992-05-12

  A process for producing difluoromaleic anhydride by reacting sulfur trioxide with a fluorinated precursor selected from the group consisting of hexafluoro-2,5-dihydrofuran, hexafluoro-2,5-dihydrothiophene, difluoro-2,5-dihydrothiophene-2,5-dione and tetrafluoro-2,5-dihydrothiophene-2-one. Also disclosed are the compounds difluoro-2,5-dihydrothiophene-2,5-dione and tetrafluoro-2,5-dihydrothiophene-2-one. Difluoromaleic anhydride is useful for example as a component of fluoropolymers.

  通过将三氧化硫与来自包括六氟-2,5-二氢呋喃、六氟-2,5-二氢噻吩、二氟-2,5-二氢噻吩-2,5-二酮和四氟-2,5-二氢噻吩-2-酮的氟化前体之一反应，制备二氟马来酸酐的方法。还披露了化合物二氟-2,5-二氢噻吩-2,5-二酮和四氟-2,5-二氢噻吩-2-酮。例如，二氟马来酸酐可用作氟聚合物的组分。
• Preparation of some highly halogenated derivative of furan
  作者：W. Dmowski、H. Voellnagel-Neugebauer

  DOI：10.1016/s0022-1139(00)82614-7

  日期：1981.9

  Direct chlorination of 2-(2H-hexafluoropropyl)-tetra- hydrofuran 1 gave high yield of 2-(2-chlorohexafluoropropyl)- pentachloro-2,5-dihydrofuran 2. Bromination of 1 gave very complex mixture of products, from which three compounds, viz. 2-bromo-5-(2H-hexafluoropropyl)-furan 3, 3-bromo-5-(2H-hexafluoropropyl)-furan 4, and 2,4-dibromo-5-(2H-hexafluoropropyl)furan 5 were isolated. Exchange fluorination

  2-（2H-六氟丙基）-四氢呋喃1的直接氯化反应产生高产率的2-（2-氯六氟丙基）-五氯-2,5-二氢呋喃2溴化反应得到非常复杂的产物混合物，其中三种化合物，即 分离出2-溴-5-（2H-六氟丙基）-呋喃3、3-溴-5-（2H-六氟丙基）-呋喃4和2,4-二溴-5-（2H-六氟丙基）呋喃5。用干燥的KF在240-300°下交换2的氟化作用，导致氟逐步取代氯，得到氯-氟-2-（2-氯六氟丙基）-二氢呋喃7,8,9和10的混合物，以及少量2-（2-氯六氟丙基）-3,4,5-三氯呋喃6。
• An abbreviated route to difluoromaleic anhydride [1]
  作者：Carl G. Krespan

  DOI：10.1016/s0022-1139(00)80218-3

  日期：1990.7
• PROCESS FOR THE PREPARATION OF DIFLUOROMALEIC ANHYDRIDE AND INTERMEDIATE COMPOUNDS PRODUCED THEREBY
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0557272B1

  公开（公告）日：1995-03-08
• ULTRAVIOLET-PERMEABLE FLUOROPOLYMERS AND PELLICLES MADE BY USING THE SAME
  申请人：ASAHI GLASS COMPANY LTD.

  公开号：EP1548014B1

  公开（公告）日：2009-04-22