Perfluoro-1,3,5-hexatriene | 392-52-9

• 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: Perfluoro-1,3,5-hexatriene
• 英文别名: trans-octafluoro-1,3,5-hexatriene；(3E)-perfluoro-1,3,5-hexatriene；perfluoro-1,4,7-octatriene；trans-Perfluoro-1,3,5-hexatriene；1,1,2,3,4,5,6,6-octafluoro-1,3,5-hexatriene；Octafluor-hexa-1,3ξ,5-trien；octafluoro-hexa-1,3,5-triene；Octafluor-hexa-1,3,5-trien；1,3,5-Hexatriene, octafluoro-；(3E)-1,1,2,3,4,5,6,6-octafluorohexa-1,3,5-triene
• CAS: 392-52-9
• 化学式: C₆F₈
• 分子量: 224.053
• InChiKey: ZSUMCLJAVFCPFL-OWOJBTEDSA-N

物化性质

• 沸点：
  65-66 °C(Press: 748 Torr)
• 密度：
  1.537 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 海关编码：
  2903399090

反应信息

• 作为反应物：
  描述：

  甲醇 、 Perfluoro-1,3,5-hexatriene 在 sodium methylate 作用下， 以85%的产率得到1,6-Dimethoxy-1,1,2,3,4,5,6,6-octafluoro-3-hexene
  参考文献：
  名称：

  Dedek, Vaclav; Linhart, Igor; Kovac, Milan, Collection of Czechoslovak Chemical Communications, 1985, vol. 50, # 8, p. 1714 - 1726

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3,4,5,6-六氯-1,1,2,3,4,5,6,6-辛氟己烷 在 乙醇 、 锌 作用下， 生成 Perfluoro-1,3,5-hexatriene
  参考文献：
  名称：

  Preparation of octafluorohexatriene

  摘要：

  公开号：

  US02705229A1

文献信息

• The stereoselective synthesis of (E)-octafluoro-1,3,5-hexatriene and (3E,5E,7E)-dodecafluoro-1,3,5,7,9-decapentaene
  作者：Qibo Liu、Donald J. Burton

  DOI：10.1016/j.jfluchem.2009.07.009

  日期：2009.10

  (E)-(1,2-Difluoro-1,2-ethenediyl)bis[tributylstannane], 3, readily undergoes a Pd(PPh3)(4)/Cul-catalyzed cross-coupling reaction with iodotrifluoroethene to yield (E)-octafluoro-1,3,5-hexatriene, 4, in high isomeric purity. (1Z,3E,5Z)-(1,2,3,4,5,6-Hexafluoro-1,3,5-hexenetriyl)bis[tributylstannane], 7, was sequentially prepared from (1Z,3E,5Z)-(1,2,3,4,5,6-hexafluoro-1,3,5-hexenetriyl)bis[triethylsilane], 5, which was prepared via a Pd(PPh3)(4)/Cul-catalyzed cross-coupling reaction of 3 with (E)-1,2-difluoro-1-iodo-2-triethylsilylethene, 6. Pd(PPh3)(4)/Cul cross-coupling of 7 with iodotrifluoroethene gave (3E,5E,7E)-dodecafluoro-1,3,5,7,9-decapentacne, 8. (C) 2009 Elsevier B.V. All rights reserved.

  (E)-(1,2-二氟乙二烯基)二二丁基ictionary，3会通过 Pd(PPh3)(4)/Cul催化的双 allen 酯反应与碘三氟乙烷发生反应，生成(E)-八氟甲基-1,3,5-三烯六烷基复合物，4在高度单一构选纯度下。若将(1Z,3E,5Z)-(1,2,3,4,5,6-六氟-1,3,5-三烯)二ictionary，7从(1Z,3E,5Z)-(1,2,3,4,5,6-六氟-1,3,5-三烯)二三乙基胺ivate，5经 Pd(PPh3)(4)/Cul催化的双 allen 酯反应生成——这里5是将3与(E)-1,2-二氟-1-碘的-2-三乙基硅ylethane发生反应所得。接着，将7与碘三氟乙烷进行 Pd催化的双 allen 酯反应，得到(3E,5E,7E)-十二氟-1,3,5,7,9-五庚烷基多戊二烯，8。2009年，Elsevier B.V. 版权所有。
• Addition of 1,2-dibromo-1-chlorotrifluoroethane to chlorotrifluoroethylene induced by uv-radiation. Synthesis of perfluoro-1,3-butadiene and perfluoro-1,3,5-hexatriene
  作者：V. Dědek、Z. Chvátal

  DOI：10.1016/s0022-1139(00)81263-4

  日期：1986.5

  5-hexadiene (VII), respectively. Photochemical reduction of butane III with 2-propanol resulted in a preferential reduction of CBr bonds, and from 2,3-dichloro-1,1,2,3,4,4-hexafluorobutane (IX) thus formed, esters of difluoroacetic acid were prepared by dehalogenation of IX and subsequent oxidation and esterification of the product. The photochemical reduction of hexane IV gave a mixture of 79% trichlorononafluorohexane

  1,2-二溴-1-氯三氟乙烷（II）与三氟氯乙烯（I）的光化学引发反应产生38％的1,4-二溴-2,3-二氯六氟丁烷（III）和19％的1,6-二溴-2,3除高级端粒外，还可以使用5-三氯九氟己烷（IV）。III和IV的脱卤作用分别用3-氯九氟-1,5-己二烯（VII）生成全氟-1,3-丁二烯（VI）和全氟-1,3,5-己三烯（VIII）。用2-丙醇对丁烷III进行光化学还原会优先还原CBr键，然后由由此形成的2,3-二氯-1,1,2,3,4,4-六氟丁烷（IX）生成二氟乙酸的酯通过IX脱卤并随后将产物氧化和酯化来制备酸。己烷IV的光化学还原得到79％三氯壬氟己烷XII和21％二氯壬氟己烷XIII的混合物。
• Thermal and UV-induced isomerization of fluorinated hexatrienes
  作者：R. Hrabal、Z. Chvátal、V. Dědek

  DOI：10.1016/s0022-1139(00)80562-x

  日期：1993.8

  0]hex- 2-ene (V). The analogous photolysis of hexatriene I in the liquid phase led to an equilibrium mixture of the starting compound I (cis-isomer) and the trans-isomer II, respectively. Photolysis of 2,3,4,5-tetrafluoro-1,3,5-hexatriene (VI) gave a mixture of cis- and trans- isomers, both in the vapour and liquid phases. Thermal reaction of hexatriene I gave octafluoro-1,3-cyclohexadiene (IV) as the

  用高压汞灯在气相中照射八氟-1,3,5-己三烯（I），得到八氟-2-乙烯基环丁烯（III）和八氟双环[2.2.0]己-2-烯（V）。液相中己三烯I的类似光解分别导致起始化合物I（顺式异构体）和反式异构体II的平衡混合物。2,3,4,5-四氟-1,3,5-己三烯（VI）的光解产生顺式和反式异构体的混合物，在气相和液相中均如此。己三烯I的热反应得到八氟-1,3-环己二烯（IV）作为唯一产物。
• Valence isomerization of fluorodienes and fluorotrienes
  作者：Richard Hrabal、Zdeněk Chvátal、Václav Dědek

  DOI：10.1016/s0022-1139(00)83396-5

  日期：1985.8
• The perfluoro-1,3,5-hexatrienes
  作者：Naiyong Jing、David M. Lemal

  DOI：10.1021/jo00086a040

  日期：1994.4

  trans-Perfluoro-1,3,5-hexatriene was obtained by catalytic isomerization of the cis isomer, and their configurations were confirmed by a photochemical method. Equilibration of these isomers with iodine and light at 13 degrees C revealed that the cis isomer is slightly more stable than the trans (K-c-->t = 0.83). The trienes undergo reactions under the influence of heat and light which contrast with those of their hydrocarbon counterparts. Cis triene cyclizes reversibly to perfluoro-3-vinylcyclobutene at 160 degrees C (K-eq = 12.2), and at higher temperatures perfluoro-1,3-cyclohexadiene is formed irreversibly. Cyclization of trans triene to the vinylcyclobutene is much slower than that of the cis isomer, as required by the finding that thermal ring opening of the vinylcyclobutene gives cis triene cleanly. Ultraviolet irradiation of the trienes with and without mercury sensitization yields the same two cyclization products, but the cyclohexadiene undergoes a further rapid photocyclization to give perfluorobicyclo[2.2.0]hex-2-ene, as reported recently by Dedek's group. Mercury photosensitization of the vinylcyclobutene proceeds smoothly to yield this same bicyclic olefin.