1-hydroxy-perfluoro-1-phenyltetralin | 519059-86-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-hydroxy-perfluoro-1-phenyltetralin
• 英文别名: 1-Hydroxyperfluoro-1-phenyl-tetralin；2,2,3,3,4,4,5,6,7,8-decafluoro-1-(2,3,4,5,6-pentafluorophenyl)naphthalen-1-ol
• CAS: 519059-86-0
• 化学式: C₁₆HF₁₅O
• 分子量: 494.159
• InChiKey: LCRHRLBHCUOKGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  1-hydroxy-perfluoro-1-phenyltetralin 在 氯化亚砜 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 78.0h， 生成 7-pentafluorophenyldecafluoro-3-chlorobicyclo[4.4.0]octa-1,4,6-triene 、 1-pentafluorophenyldecafluoro-1-chlorotetralin
  参考文献：
  名称：

  摘要：

  The reactivity of perfluorinated benzocyclobutene, indan, and tetralin in reaction with pentafluorobenzene in SbF5 medium, and also the relative stability of generated therewith perfluoro-1-phenyl-benzocycloalkenyl cations decrease with increasing alicyclic fragment in the benzocycloalkene. Treating the solutions of salts of the above cations with anhydrous HF results in the corresponding perfluoro-1-phenylbenzocycloalkenes, and the hydrolysis of salts furnishes their 1-hydroxy derivatives. In a reaction of 1-hydroxyperfluoro-1-phenylbenzocyclobutene, -indan, and -tetralin with SOCl2 the hydroxy group is replaced by chlorine. Besides with indan and tetralin derivatives form respectively 7-pentafluorophenyl-octafluoro-3-chlorobicyclo[4.3.0]hepta- 1,4,6-triene and 7-pentafluorophenyldecafluoro-3-chlorobicyclo[4.4.0]octa-1,4,6-triene.

  DOI：

  10.1023/a:1020901526459
• 作为产物：
  描述：

  五氟苯 、 perfluorotetralin 在 六氟苯 、 五氟化锑 、 水 作用下， 反应 6.0h， 以1.73 g的产率得到1-hydroxy-perfluoro-1-phenyltetralin
  参考文献：
  名称：

  摘要：

  The reactivity of perfluorinated benzocyclobutene, indan, and tetralin in reaction with pentafluorobenzene in SbF5 medium, and also the relative stability of generated therewith perfluoro-1-phenyl-benzocycloalkenyl cations decrease with increasing alicyclic fragment in the benzocycloalkene. Treating the solutions of salts of the above cations with anhydrous HF results in the corresponding perfluoro-1-phenylbenzocycloalkenes, and the hydrolysis of salts furnishes their 1-hydroxy derivatives. In a reaction of 1-hydroxyperfluoro-1-phenylbenzocyclobutene, -indan, and -tetralin with SOCl2 the hydroxy group is replaced by chlorine. Besides with indan and tetralin derivatives form respectively 7-pentafluorophenyl-octafluoro-3-chlorobicyclo[4.3.0]hepta- 1,4,6-triene and 7-pentafluorophenyldecafluoro-3-chlorobicyclo[4.4.0]octa-1,4,6-triene.

  DOI：

  10.1023/a:1020901526459

文献信息

• 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。
• The alicyclic ring contraction of perfluoro-1-phenyltetralin in reaction with antimony pentafluoride
  作者：Vladimir R Sinyakov、Tatyana V Mezhenkova、Victor M Karpov、Vyacheslav E Platonov

  DOI：10.1016/j.jfluchem.2003.09.006

  日期：2004.1

  Perfluoro-1-phenyltetralin (1) heated with antimony pentafluoride at 130 °C, then treated with water, gave a mixture of perfluorinated 3-methyl-2-phenylindenone (3), 3-methyl-2-phenylindene (4), 3-hydroxy-1-methyl-3-phenylindan (5), 1-methyl-3-phenylindan (6), 9-methyl-1,2,3,4,5,6,7,8-octahydroanthracene (7), and 1,9-dimethyl-5,6,7,8-tetrahydro-β-naphthindan (8). When heated with SbF5 in the presence

  将全氟-1-苯基四氢化萘（1）与五氟化锑在130°C下加热，然后用水处理，得到全氟3-甲基-2-苯基茚满酮（3），3-甲基-2-苯基茚满（4），3的混合物-羟基-1-甲基-3-苯基茚满（5），1-甲基-3-苯基茚满（6），9-甲基-1,2,3,4,5,6,7,8-八氢蒽（7），和1,9-二甲基-5,6,7,8-四氢-β-萘丁酮（8）。当与加热的SbF 5在HF的存在下，然后用水处理，化合物1转化为产物的混合物3 - 6。在170和200°C下反应形成化合物3– 6和全氟-2-（环己烯-1-基）-3-甲基茚（10）。
• Carbonylation of Polyfluorinated 1-Arylalkan-1-ols and Diols in Superacids
  作者：Siqi Wang、Yaroslav V. Zonov、Victor M. Karpov、Olga A. Luzina、Tatyana V. Mezhenkova

  DOI：10.3390/molecules27248757

  日期：——

  We describe the carbonylation of a series of mono and dihydroxy derivatives of polyfluorinated alkylbenzenes and benzocycloalkenes with OH groups at benzylic positions using carbon monoxide in the presence of a superacid (TfOH, a TfOH-SbF5 mixture, or a FSO3H-SbF5 mixture). It was shown that the superacid-catalyzed addition of CO to various primary and secondary polyfluorinated alcohols and diols gives

  我们描述了在存在超酸（TfOH、TfOH-SbF5 混合物或 FSO3H-SbF5 混合物）的情况下使用一氧化碳在苄基位置具有 OH 基团的多氟化烷基苯和苯并环烯烃的一系列单羟基和二羟基衍生物的羰基化。结果表明，超强酸催化的 CO 加成到各种伯和仲多氟化醇和二醇中会产生相应的一元和二元羧酸或内酯。评估了取决于醇结构的各种超强酸的效率，FSO3H-SbF5 在大多数转化中产生了最好的结果。发现将 CO 加成到含有邻位氟原子的仲 1-arylalkan-1-ols 伴随着 HF 的消除以及 α,β-不饱和芳基羧酸的形成。与伯醇和仲醇相比，