perfluoro(1-isopropyl-1,2-dihydrocyclobutabenzene) | 103634-36-2

• 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-isopropyl-1,2-dihydrocyclobutabenzene)
• 英文别名: perfluoro-1-isopropyl-1,2-dihydrobenzocyclobutene；perfluoro-1-isopropylbenzocyclobutene；2,3,4,5,7,7,8-Heptafluoro-8-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)bicyclo[4.2.0]octa-1,3,5-triene；2,3,4,5,7,7,8-heptafluoro-8-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)bicyclo[4.2.0]octa-1(6),2,4-triene
• CAS: 103634-36-2
• 化学式: C₁₁F₁₄
• 分子量: 398.099
• InChiKey: QTYGPRCHPTTYIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  perfluoro(1-isopropyl-1,2-dihydrocyclobutabenzene) 在 五氟化锑 、 silica gel 作用下， 反应 5.0h， 以90%的产率得到perfluoro-2-isopropylbenzocyclobutanone
  参考文献：
  名称：

  在SiO 2 / SbF 5的作用下全氟化的1-烷基-，1-苯基-和1,2-二烷基苯并环丁烯的转化

  摘要：

  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

  DOI：

  10.1016/j.jfluchem.2012.11.004
• 作为产物：
  描述：

  六氟丙烯 、 perfluorobenzocyclobutene 在 五氟化锑 作用下， 反应 45.0h， 生成 perfluoro(1-isopropyl-1,2-dihydrocyclobutabenzene)
  参考文献：
  名称：

  Reactions of perfluorinated benzocyclobutene and 1-methylbenzocyclobutene with fluoroolefins in the presence of SbF5

  摘要：

  DOI：

  10.1007/bf00963251

文献信息

• Generation of perfluorinated 1-alkylbenzocyclobuten-1-yl and 1-alkylindan-1-yl cations. On paradoxical stabilizing influence of an electron-withdrawing perfluoroisopropyl group on the relative stabilities of the cations
  作者：Tatyana V. Mezhenkova、Victor M. Karpov、Irina V. Beregovaya、Yaroslav V. Zonov、Igor P. Chuikov、Vyacheslav E. Platonov

  DOI：10.1016/j.jfluchem.2016.10.009

  日期：2016.12

  alkylbenzocycloalken-1-yl cations containing a fluorine atom or a perfluoroalkyl group in the cationic centre were generated. Contrary to expectations, a number of stable long‐lived perfluoro-1-isopropylbenzocycloalken-1-yl cations containing an electron-withdrawing perfluoroisopropyl group in the cationic centre have been obtained. The DFT (B3LYP/6-31G*) calculations showed that the relative stabilities of isomeric

  当将全氟-1-烷基苯并环丁烯和-茚满溶解在过量的SbF 5中时，会产生在阳离子中心含有氟原子或全氟烷基的全氟烷基苯并环烯-1-基阳离子。与预期相反，已获得许多在阳离子中心含有吸电子全氟异丙基的稳定的长寿命全氟-1-异丙基苯并环烯基-1-基阳离子。DFT（B3LYP / 6-31G *）计算表明，从CF 3移出时，阳离子中心含氟原子或全氟烷基的异构阳离子的相对稳定性发生变化，有利于阳离子中心含全氟烷基的阳离子。到CF（CF 3）2 这与实验数据一致。
• Skeletal transformations of pentafluorophenylation products of perfluorinated 1,2-dialkyl-1,2-dihydrocyclobutabenzenes in SbF5
  作者：T. V. Mezhenkova、V. R. Sinyakov、V. M. Karpov、V. E. Platonov

  DOI：10.1134/s1070428013100096

  日期：2013.10

  Perfluorinated 1-ethyl-2-methyl- and 1-isopropyl-2-methyl-1,2-dihydrocyclobutabenzenes reacted with pentafluorobenzene in SbF5 to generate perfluoro(1-ethyl-2-methyl-2-phenyl- and perfluoro(1-izopropyl-2-methyl-2-phenyl-1,2-dihydrocyclobutabenzen-1-yl) cations. These cations in SbF5 at 20A degrees C underwent opening of the four-membered ring and its expansion to five-membered. After hydrolysis, perfluorinated 4-[1-(2-propylphenyl)ethylidene]- and 4-[1-(2-isobutylphenyl)ethylidene]-2,5-cyclohexadien-1-ones were obtained together with perfluoro(3-ethyl- and perfluoro(3-isopropyl-2-phenylinden-1-ones).
• Selective ortho-arylation of fluorinated phenols and naphthols by lead arylacetates
  作者：V.N. Kovtonyuk、L.S. Kobrina

  DOI：10.1016/s0022-1139(00)83820-8

  日期：1991.9
• Formation of perfluorinated 1,2-dialkylbenzenes from perfluoroalkylbenzocyclobutenes in the system I2-SbF5
  作者：T. V. Mezhenkova、V. M. Karpov、V. E. Platonov

  DOI：10.1134/s1070428010090277

  日期：2010.9
• Rearrangement of the carbon skeletion of perfluorinated 1-isopropyl-, 1-methyl-1-isopropyl-, and 1-methyl-2-isopropylbenzocyclobutenes by the action of antimony pentafluoride
  作者：V. M. Karpov、T. V. Mezhenkova、V. E. Platonov

  DOI：10.1007/bf00866598

  日期：1992.6

  Perfluorinated 1-isopropyl-, 1-methyl-1-isopropyl-, and 1-methyl-2-isopropylbenzocyclobutenes isomerize under the influence of antimony pentafluoride to perfluorinated alkylstyrenes and alkylindans. The process may be accompanied by dealkylation and also by fluorination and defluorination of the products. With antimony pentafluoride at 50-degrees-C perfluoro-1-methyl-1-isopropylbenzocyclobutene gives perfluoro-alpha,beta,beta,o-tetramethylstyrene, which isomerizes under the influence of antiniony pentafluoride at 130-degrees-C into perfluoro-1,2,2-trimethylindan, and the latter forms perfluoro-2,3-dimethylindene under the reaction conditions. Perfluoro-1-methyl-2-isopropylbenzocyclobutene is not changed in the presence of antimony pentafluoride at 50-degrees-C but isomerizes to perfluoro-1-isopropylindan at 90-degrees-C. The latter is transformed under these conditions into the above-mentioned tetramethylstyrene. Perfluoro-1-isopropylbenzocyclobutene does not react with antimony pentafluoride at 130-degrees-C, but at 170-degrees-C it gives a mixture of perfluorinated 2,2-dimethylindan, 2,3-dimethylindene, 2,3-dimethyl-4,5,6,7-tetrahydroindene, and 2-isobutyltoluene, which is converted into perfluoro-o-xylene under the reaction conditions.