perfluoro-1,2-diethylbenzocyclobutene | 94117-85-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: perfluoro-1,2-diethylbenzocyclobutene
• 英文别名: Perfluoro-1,2-diethylbenzocyclobutane；2,3,4,5,7,8,-Hexafluoro-7,8-bis(pentafluoroethyl)bicyclo[4,2,0]octa-1,3,5-trien；2,3,4,5,7,8-hexafluoro-7,8-bis(1,1,2,2,2-pentafluoroethyl)bicyclo[4.2.0]octa-1(6),2,4-triene
• CAS: 94117-85-8
• 化学式: C₁₂F₁₆
• 分子量: 448.106
• InChiKey: YRDQAGHEVFXDBK-UHFFFAOYSA-N

物化性质

• 沸点：
  75-77 °C(Press: 21 Torr)
• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  perfluoro-1,2-diethylbenzocyclobutene 在 五氟化锑 作用下， 70.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 perfluoro-1,4-diethylisochromen-1-yl cation
  参考文献：
  名称：

  在CO / SbF 5的作用下，全氟1,2-二烷基-，1,1-和1,2-烷基苯并环丁烯向茚满-2-一和异色烯衍生物的转化

  摘要：

  全氟1,2-二烷基苯并环丁烯在室温下与CO–SbF 5和50°C下全氟-1-甲基-2-苯基苯并环丁烯的相互作用产生了氟茚满-2-一衍生物。当反应温度升至70°C时，在两种情况下均会形成多氟异色烯衍生物。在用H 2 O处理反应混合物后，全氟-1-乙基-1-苯基苯并环丁烯与CO–SbF 5的相互作用在70°C下产生了全氟-3-乙基-3-苯基茚满-1,2-二酮。

  DOI：

  10.1016/j.jfluchem.2016.06.014
• 作为产物：
  描述：

  四氟乙烯 、 perfluorobenzocyclobutene 在 五氟化锑 作用下， 反应 8.0h， 生成 perfluoro-1,2-diethylbenzocyclobutene 、 perfluoro-1,1-diethylbenzocyclobutene
  参考文献：
  名称：

  Karpov, V. M.; Mezhenkova, T. V.; Platonov, V. E., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1220 - 1221

  摘要：

  DOI：

文献信息

• Transformations of perfluorinated 1-alkyl-, 1-phenyl- and 1,2-dialkylbenzocyclobutenes under the action of SiO2/SbF5
  作者：Yaroslav V. Zonov、Victor M. Karpov、Vyacheslav E. Platonov、Tatjana V. Rybalova

  DOI：10.1016/j.jfluchem.2012.11.004

  日期：2013.1

  Heating of perfluorinated 1-methyl-, 1-ethyl- and 1-isopropylbenzocyclobutenes with SiO2 in an SbF5 medium at 75 °C results in perfluoro-2-alkylbenzocyclobutenones or perfluoro-3-alkylphthalides formation. Perfluorinated 1,2-diethyl- and 1-ethyl-2-methylbenzocyclobutenes react with SiO2/SbF5 at 75 °C to form, after treatment of the reaction mixture with water, perfluorinated 1,3-diethyl- and 1-eth

  加热全氟化1-甲基，1-乙基和1- isopropylbenzocyclobutenes用的SiO 2中的SBF 5在75℃下的结果中全氟-2- alkylbenzocyclobutenones或全氟-3- alkylphthalides形成。全氟化1,2-二乙基和1-乙基-2- methylbenzocyclobutenes与反应的SiO 2 /的SbF 5在75℃，以形成，治疗与水的反应混合物的后，全氟化1,3-二乙基和1-乙基3-甲基邻苯二甲酸-1,3-二醇。全氟-1,2- diisopropylbenzocyclobutene的SiO的作用下2 /的SbF 5在95℃将其转化为全氟-7,8-二异丙基双环[4.2.0]八-1,5,7-三烯-3,4-二酮和全氟-1，2-二异丁酰基苯。全氟-1-甲基-2-苯基苯并环丁烯在75°C的SbF 5介质中不与SiO 2反应，全氟-1-苯基苯并环丁
• The alicyclic ring cleavage and other transformations of perfluorinated 1-alkyl-, 1,1- and 1,2-dialkyl-benzocyclobutenes in the system Br2SbF5
  作者：V.M. Karpov、T.V. Mezhenkova、V.E. Platonov

  DOI：10.1016/0022-1139(96)03390-8

  日期：1996.4

  of the aromatic ring and breaking of the C1C2 bond of the four-membered ring. Thus, in the Br2SbF5 system, compound 5 gives 4-bromoperfluoro-1,2-dipropylcyclohexene (10) and perfluoro-1,2-dipropylcyclohexene (11), and isomer 4 gives perfluoro-1,1-diethyl-3,4,5,6-tetrahydrobenzocyclobutene (15) and perfluoro-1-methyl-2-(pent-2-ene-3-yl)cyclohexene (16). The latter is obtained by heating compound 15

  在SbF 5介质中，全氟化的1-甲基-（2）和1-乙基-苯并环丁烯（3）与溴反应，将起始化合物的四元环裂解，得到2-溴全氟异丙基苯（8）和2-分别观察到溴过氟仲丁基苯（9）。在该系统中溴2 SbF 5，全氟化1,1-（4）和1,2- diethylbenzocyclobutene（5）经历芳环的bromofluorination以及C的分断1 C 2的四元环的键。因此，在BR 2 SbF 5在体系中，化合物5得到4-溴全氟-1，2-二丙基环己烯（10）和全氟1,2，2-二丙基环己烯（11），异构体4得到全氟-1，1-二乙基-3，4，5，6-四氢苯并环丁烯。 （15）和全氟-1-甲基-2-（戊-2-烯-3-基）环己烯（16）。后者是通过将化合物15与SbF 5或CsF加热而获得的。
• Expansion of the pentafluorobenzene ring and other skeletal transformations in the reaction of perfluoro(1,2-diethyl-1-phenyl-1,2-dihydrocyclobutabenzene) with antimony pentafluoride
  作者：T. V. Mezhenkova、V. R. Sinyakov、V. M. Karpov、V. E. Platonov

  DOI：10.1134/s1070428012040112

  日期：2012.4

  The reaction of perfluoro(1-phenyl-1,2-diethyl-1,2-dihydrocuclobutabenzene) with SbF5 at 20°C, followed by treatment of the reaction mixture with water gave perfluoro 4-[1-(2-propylphenyl)propylidene]-2,5-cyclohexadien-1-one} together with perfluoro[4b,10-diethylbenzo[a]azulen-7(4bH)-one] resulting from unusual expansion of the pentafluorobenzene ring to seven-membered ring. Analogous reaction at 90°C

  全氟（1-苯基-1,2-二乙基-1,2-二氢氯丁苯）与SbF5在20°C下反应，然后将反应混合物用水处理，得到全氟4- [1-（2-丙基苯基）亚丙基] -2,5-环己二烯-1-酮}与全氟[4b，10-二乙基苯并[ a ] azulen-7（4b H）-one]共同作用，是由于五氟苯环异常膨胀为七元环所致。除上述化合物外，在90°C进行类似反应，通过从七元碳原子中除去C 2 F 5基团，得到全氟10-乙基和3,10-二乙基苯并[ a ] azulen-6（10 H）-环或其向苯环的迁移。
• Expansion of the pentafluorobenzene ring of perfluoro-1,2-diethyl-1-phenylbenzocyclobutene under the action of SbF5
  作者：Tatyana V. Mezhenkova、Vladimir R. Sinyakov、Victor M. Karpov、Vyacheslav E. Platonov、Tatjana V. Rybalova、Yuri V. Gatilov

  DOI：10.1016/j.jfluchem.2007.09.005

  日期：2008.1

  Perfluoro-1,2-diethyl-1-phenylbenzocyclobutene under the action of SbF5 gives, after treatment of the reaction mixture with water, perfluoro-4-[1-(6-propyl-phenyl)-propylidene]cyclohexa-2,5-dienone along with the products of unusual pentafluorobenzene ring expansion - perfluorinated 4b,10-diethylbenzo[a]azulen-7(4bH)-one and 10-ethylbenzo[a]azulen-6(10H)-one. (C) 2007 Elsevier B.V. All rights reserved.
• Skeletal reactions of perfluoromethylethyl- and perfluorodiethylbenzocyclobutenes with 1,1- and 1,2-alkyl groups in SbF5
  作者：V. M. Karpov、T. V. Mezhenkora、V. E. Platonov、G. G. Yakobson�

  DOI：10.1007/bf00961700

  日期：1990.5

  Taking perfluoro-1,1-dialkylbenzocyclobutenes as examples, it has been shown to be possible to enlarge the four-membered ring in polyfluorobenzocyclobutenes to five-membered in the presence of SbF5, by cleavage of the four-membered ring followed by cyclization of the resulting polyfluorostyrene to the polyfluoroindane, which then undergoes further reactions. Perfluoro-1-methyl-1-ethylbenzocyclobutene isomerizes at 50-degrees-C in the presence of SbF5 to perfluoro-alpha,beta-omicron-trimethylstyrene, which is reversibly converted at 130-degrees-C into perfluoro-1,2-dimethylindane. Perfluoro-1,1-diethylbenzocyclobutene isomerizes at 130-degrees-C in the presence of SbF5 to give perfluoro-alpha-ethyl-beta,o-dimethylstyrene, which at 170-degrees-C gives perfluoro-2-methyl-3-ethylindene- and perfluoro-2-methyl-3-ethyl-4,5,6,7-tetrahydroindene. The last two compounds, together with perfluoro-o-dipropylbenzene, are obtained from perfluoro-1,2-diethylbenzocyclobutene with SbF5 at 170-degrees-C. From perfluoro-1-methyl-2-ethyl-benzocyclobutene with SbF5 at 95-degrees-C there is obtained perfluoro-1-ethylindane, while at 130-degrees-C, in addition to the latter compound, there are obtained perfluorinated 1,1-dimethylindane, 1,2-dimethylindane, alpha,beta,o-trimethylstyrene, 2,3-dimethylindene, and 2,3-dimethyl-4,5,6,7-tetrahydroindene.