perfluoro-1-ethylindan | 98583-34-7

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: perfluoro-1-ethylindan
• 英文别名: perfluoro-1-ethylindane；1,1,2,2,3,4,5,6,7-nonafluoro-3-(1,1,2,2,2-pentafluoroethyl)indene
• CAS: 98583-34-7
• 化学式: C₁₁F₁₄
• 分子量: 398.099
• InChiKey: VUFBIYXHIKEIJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 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-ethylindan 在 五氟化锑 、 silica gel 作用下， 反应 7.0h， 以85%的产率得到perfluoro(4-fluorocarbonyl-3-methylisochromenyl) cation
  参考文献：
  名称：

  Reaction of perfluoro-1-ethylindan with SiO2/SbF5 and skeletal transformations of perfluoro-3-ethylindan-1-one under the action of SbF5 and SiO2/SbF5

  摘要：

  Perfluoro-1-ethylindan heated with excess of SiO2 in an SbF5 medium at 75 degrees C and then treated with water, gives 4-carboxy-perfluoro-3methylisochromen- 1-one. Perfluoro-3-ethylindan-1-one is converted, under the action of SbF5 at 70 degrees C, to perfluoro-2-(but-2-en-2-yl)benzoic acid as a mixture of E- and Z-isomers. When the reaction temperature is raised to 125 degrees C, a solution of salts of perfluoro-3,4-dimethyl-1 H-isochromen-1-yl and perfluoro-4-ethyl-1H-isochromen-1-yl cations is obtained. Increase in the reaction time lowers the content of a salt of the latter cation in the solution. Hydrolysis of the solution of the salts gives perfluoro-3,4-dimethylisochromen-1-one and perfluoro-4-ethylisochromen-1-one. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.05.021
• 作为产物：
  描述：

  perfluoroindane 、 四氟乙烯 、 五氟化锑 生成 perfluoro-1-ethylindan
  参考文献：
  名称：

  KARPOV, V. M.;MEZHENKOVA, T. V.;PLATONOV, V. E.;YAKOBSON, G. G., ZH. ORGAN. XIMII, 1984, 20, N 6, 1341-1342

  摘要：

  DOI：

文献信息

• Interaction of perfluorobenzocycloalkenes with tetrafluoroethylene in the presence of SbF5
  作者：V.M. Karpov、T.V. Mezhenkova、V.E. Platonov、G.G. Yakobson

  DOI：10.1016/s0022-1139(00)85198-2

  日期：1985.5

  perfluoro-1-ethylbenzocycloalkenes transformed further to disubstituted derivatives. In the case of perfluorotetralin, the reaction gave perfluoro-1,4-diethyltetralin. Perfluorobenzocyclobutene gave perfluoro-1,1- and -1,2-diethylbenzocyclobutenes in about equal quantities, and perfluoroindan- practically only perfluoro-1,1-diethylindan. To explain this orientation, the electronic and steric effects are considered

  在SbF 5的存在下，全氟四氢化萘，茚满和苯并环丁烯与四氟乙烯的反应导致进一步转化为二取代衍生物的全氟-1-乙基苯并环烯烃的形成。在全氟四氢萘的情况下，反应得到全氟-1，4-二乙基四氢萘。全氟苯并环丁烯产生的全氟-1,1-和-1,2-二乙基苯并环丁烯的数量大致相等，而全氟茚满-实际上仅是全氟-1,1-二乙基二茚。为了解释这种取向，考虑了电子和空间效应，它们可以影响中间碳阳离子的反应性和相对稳定性。
• Carbonylation of polyfluorinated indans, tetralins and perfluoro-2,3-dihydrobenzofuran under the action of CO/SbF5
  作者：Yaroslav V. Zonov、Victor M. Karpov、Tatyana V. Mezhenkova、Vyacheslav E. Platonov

  DOI：10.1016/j.jfluchem.2018.07.014

  日期：2018.10

  Perfluoroindan and its 4-CF3, 5-CF3, 5-CH3, 1,1-H,H derivatives add two CO molecules to form the corresponding dimethyl indan-1,1-dicarboxylates after methanolysis, and/or 1-hydroindan-1-carboxylic acids after hydrolysis. 1-X-Perfluoroindans (XCF3, C2F5, C6F5, H) and 1-X-perfluorotetralins (XC2F5, C6F5) add one CO molecule at the 1-position to give the corresponding 1-carbonyl fluorides. Reaction of the latter

  在室温和大气压下，在CO / SbF 5的作用下，将多氟茚满和四氢化萘羰基化。Perfluoroindan及其4-CF 3，5-CF 3，5-CH 3，1,1- H，H的衍生物添加两个CO分子以形成相应的甲醇分解后二甲基茚满-1,1-二羧酸，和/或1-水解后的氢化茚满-1-羧酸。1-X-全氟茚满（X CF 3，C 2 F 5，C 6 F 5，H）和1-X-全氟四氢化萘（X C 2 F 5，C 6 F 5））在1位加一个CO分子，得到相应的1-羰基氟化物。后者与甲醇反应得到甲酯，而水解伴随脱羧作用。全氟-2,3-二氢苯并呋喃在CO / SbF 5的作用下同时生成单羰基和二羰基化产物。
• 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。
• Generation of Perfluoro- and 1-Chloroperfluoro-Indanyl and -Benzocyclobutenyl Cations with Perfluoroalkyl Groups in the Aliphatic Ring
  作者：T. V. Mezhenkova、V. M. Karpov、Ya. V. Zonov、I. P. Chuikov

  DOI：10.1134/s1070428019020118

  日期：2019.2

  groups in the alicyclic fragment. The cations exist in equilibrium with their precursors. Adding SO2Cl2 to the system led to the formation of polyfluoroalkylbenzocycloalken-1-yl cations with a chlorine substituent at the cationic center. The structures of the cations were determined by 19F and 13C NMR spectroscopy and confirmed by the structures of perfluoroketones formed on their hydrolysis.

  在SbF 5 -SO 2 ClF介质中，由脂环片段中含有全氟烷基的全氟茚满和苯并环丁烯衍生物生成了全氟（烷基苯并环烯-1-基）阳离子。阳离子与其前体平衡存在。将SO 2 Cl 2添加到体系中导致形成在阳离子中心带有氯取代基的多氟烷基苯并环烯-1-基阳离子。阳离子的结构通过19 F和13 C NMR光谱测定，并通过其水解形成的全氟酮的结构证实。
• Transformation of perfluorinated benzocycloalkenes and alkylbenzenes to their carbonyl derivatives under the action of CF3COOH/SbF5
  作者：Yaroslav V. Zonov、Victor M. Karpov、Vyacheslav E. Platonov

  DOI：10.1016/j.jfluchem.2007.05.020

  日期：2007.9

  Perfluorinated benzocycloalkenes (benzocyclobutene, indan, tetralin), alkylbenzocycloalkenes and alkylbenzenes react with CF3COOH/SbF5 at 20-50 degrees C giving the corresponding carbonyl derivatives. (c) 2007 Elsevier B.V. All rights reserved.