四氟乙烯五聚体 | 52584-41-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 中文名称: 四氟乙烯五聚体
• 英文名称: Perfluoro(4-ethyl-3,4-dimethylhex-2-ene)
• 英文别名: perfluoro-3,4-dimethyl-4-ethyl-2-hexene；perfluoro-4-ethyl-3,4-dimethylhex-2-ene；Tetrafluoroethene pentamer；2-Hexene, 4-ethyl, 3,4-dimethyl, perfluoro-；(E)-1,1,1,2,5,5,6,6,6-nonafluoro-4-(1,1,2,2,2-pentafluoroethyl)-3,4-bis(trifluoromethyl)hex-2-ene
• CAS: 52584-41-5
• 化学式: C₁₀F₂₀
• 分子量: 500.078
• InChiKey: WUPIJZMVJFXUOO-OWOJBTEDSA-N

物化性质

• 沸点：
  151.5±8.0 °C(Predicted)
• 密度：
  1.688±0.06 g/cm3(Predicted)
• 保留指数：
  409

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  四氟乙烯五聚体 在 monoflor 31 、 三乙胺 作用下， 以 二乙二醇二甲醚 、 水 为溶剂， 反应 18.0h， 以61%的产率得到Perfluoro-4-ethyl-2,3,4,5-tetramethyl-4,5-dihydrofuran
  参考文献：
  名称：

  四氟乙烯低聚物的反应。第十三部分。全氟化二氢呋喃的反应；全氟-4-乙基-2,3,4,5-四甲基-4,5-二氢呋喃

  摘要：

  由四氟乙烯五聚体制备的全氟化二氢呋喃，全氟-4-乙基-2,3,4,5-四甲基-4,5-二氢呋喃PFDHF（1）与一系列亲核试剂反应。发现形成的产物的类型取决于所使用的亲核试剂。发现氧，硫和碳亲核试剂攻击发生在2位，而氮亲核试剂攻击发生在2位或环外3位。

  DOI：

  10.1016/s0022-1139(00)82235-6

文献信息

• Polyfluoro-1,2-epoxy-alkanes and -cycloalkanes. Part III. Some 1,2-epoxides derived from oligomers of tetrafluoroethylene
  作者：Paul L. Coe、Alan Sellars、John Colin Tatlow

  DOI：10.1016/s0022-1139(00)84973-8

  日期：1983.8

  (C2F5)2(CF3)C−; R2 = (C2F5)(CF3)(F)C−; R3 = F) reacted with aqueous sodium hypochlorite/ acetonitrile to give high yields of the corresponding 1,2-epoxides. Perfluoro-1-methyl-2-(1-methylpropyl)cyclobutene (derived from the hexamer by pyrolysis) and perfluoro-4-ethyl-2,3,4,5-tetramethyl-4,5-dihydrofuran (made by hydrolysis of the pentamer) also underwent efficient epoxidation. The epoxy-oxolan decomposed in two

  三个低聚物（[R 1 ] [R 2 ] C = C [R 3 ] [F]）四氟乙烯，三聚体（R 1 = C 2 ˚F 5 - ; R 2 = R 3 = CF 3 - ），五聚体（R 1 =（C 2 ˚F 5）2（CF 3）C-; R 2 = R 3 = CF 3 - ）和六聚体的主要异构体（R 1 =（C 2 ˚F 5）2（CF 3）C- ； R 2＝（C 2 F 5）（CF 3）（F）C-；R 3＝ F）与次氯酸钠/乙腈水溶液反应，得到高产率的相应的1,2-环氧化物。全氟-1-甲基-2-（1-甲基丙基）环丁烯（通过热解衍生自六聚体）和全氟-4-乙基-2,3,4,5-四甲基-4,5-二氢呋喃五聚体）也进行了有效的环氧化。环氧-氧杂戊烷在280–480°C下以两种方式分解，一种过程可能通过自由基途径生成四氟乙烯的三聚体，另一种过程涉及到氟离子，生成十四氟-3,4-二甲基己基-3-烯-2-一
• Reactions of tetrafluoroethene oligomers. Part 16. The synthesis and reactions of perfluoro[2,3-dimethyl-2-(3-methylpentan-3-yl)]-2H-azirine: a source of 2,3-bis(trifluoromethyl)aziridine derivatives
  作者：Paul L. Coe、Michael I. Cook

  DOI：10.1039/b001456g

  日期：——

  The reaction of perfluoro(4-ethyl-3,4-dimethylhex-2-ene) (TFE pentamer) with sodium azide in acetonitrile afforded perfluoro[2,3-dimethyl-2-(3-methylpentan-3-yl)]-2H-azirine as a stable distillable liquid. The azirine reacted slowly with nucleophiles to give a series of substituted 2,3-bis-(trifluoromethyl)aziridines. A rationale of this somewhat unexpected reaction is suggested.

  的反应 全氟（4-乙基-3,4-二甲基己-2-烯） （TFE五聚体）与 叠氮化钠 在 乙腈得到全氟[2,3-二甲基-2-（3-甲基戊-3-基）] - 2 ħ -azirine作为稳定的蒸馏液。这方位角与亲核试剂缓慢反应，得到一系列取代的2,3-双-（三氟甲基）氮丙啶。提出了这种有点出乎意料的反应的原理。
• Bayliff, Andrew E.; Bryce, Martin R.; Chambers, Richard D., Journal of the Chemical Society. Perkin transactions I, 1987, p. 763 - 768
  作者：Bayliff, Andrew E.、Bryce, Martin R.、Chambers, Richard D.

  DOI：——

  日期：——
• Chambers, Richard D.; Kirk, Julian R.; Powell, Richard L., Journal of the Chemical Society. Perkin transactions I, 1983, p. 1239 - 1242
  作者：Chambers, Richard D.、Kirk, Julian R.、Powell, Richard L.

  DOI：——

  日期：——
• On the structure of the perfluorinated F-4-ethyl-3,4-dimethyl-hexan-3-yl carbanion: a structural dynamic -DNMR study
  作者：Udo Groß、Dietmar Pfeifer

  DOI：10.1016/s0022-1139(01)00433-x

  日期：2002.1

  The perfluoro-4-ethyl-3,4-dimethylhexan-3-yl carbanion was prepared by reaction of tetramethylammonium fluoride with the parent C2F4-pentamer olefin in acetonitrile as a stable but moisture sensitive white salt. C-13- and F-19-NMR spectra of the carbanion were recorded, whereby the latter is first order with exception of the AB-type spectrum of the prochiral CF2(5)-groups.Low-temperature NMR spectra down to -90 degreesC show dynamic behavior, and a step-wise freezing out of molecular rotations occurs. Activation energies of such barriers of interconversion and rate constants were determined from spectral data. Likewise, the carbanion site structure is described. In addition, the molecular structure and its rotational isomers are calculated by the quantum chemical AM 1 method. As the major structural result, the carbanion site is flat and sp(2) hybridized in contrast to an inverting pyramidal carbon atom. This planar arrangement is confirmed by the occurrence of diastereotopic fluorines of the CF2(2) group in the molecule, where the equatorial fluorine of that group is locked in the plane of the perpendicular p(z)-orbital.Fluorine containing groups in the neighborhood of the lone electron pair of the anion suffer strong electron deshielding and a remarkable F-19-NMR downfield shift takes place as a consequence of a chemical shift anisotropy. (C) 2002 Elsevier Science B.V. All rights reserved.