cis-perfluoro-2-butenoyl-fluoride | 20377-93-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: cis-perfluoro-2-butenoyl-fluoride
• 英文别名: perfluoro-cis-crotonoyl fluoride；cis-CF3CF=CFCFC(O)F；Perfluorisocrotonoyl-fluorid；(Z)-2,3,4,4,4-pentafluorobut-2-enoyl fluoride
• CAS: 20377-93-9
• 化学式: C₄F₆O
• 分子量: 178.034
• InChiKey: KBGQISMERZUWBT-UPHRSURJSA-N

物化性质

• 沸点：
  45.8±40.0 °C(Predicted)
• 密度：
  1.513±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  全氟-2,3-二氢呋喃 在 五氟化锑 作用下， 反应 6.0h， 以88%的产率得到cis-perfluoro-2-butenoyl-fluoride
  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

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.SVol.3, 6.2.2, page 1 - 48
  作者：

  DOI：——

  日期：——
• A 19F NMR study of products of hexafluorobutadiene sulfotrioxidation
  作者：N. V. Lebedev、G. A. Emel’yanov、F. A. Makhmutov、D. D. Moldavskii、V. V. Berenblit

  DOI：10.1134/s1070427207030147

  日期：2007.3

  The products of hexafluorobutadiene sulfotrioxidation were identified by F-19 NMR. The major products are hexafluoro-1-butene-3,4-beta-sultone, hexafluoro-2-butene-1,4-sultone, hexafluoro-1-butene-3,4-pyrosultone, and hexafluoro-2-buten-1,4-diyl sulfate.
• Kaz'mina, N. B.; Knunyants, I. L.; Mysov, E. I., Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1978, p. 142 - 149
  作者：Kaz'mina, N. B.、Knunyants, I. L.、Mysov, E. I.、Kuz'yants, G. M.

  DOI：——

  日期：——
• 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.