全氟苯并环丁烯酮 | 59514-38-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 中文名称: 全氟苯并环丁烯酮
• 英文名称: perfluorobenzocyclobutenone
• 英文别名: 2,3,4,5,8,8-hexafluorobicyclo[4.2.0]octa-1(6),2,4-trien-7-one
• CAS: 59514-38-4
• 化学式: C₈F₆O
• 分子量: 226.078
• InChiKey: POMGQPVDVSKTOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  全氟苯并环丁烯酮 在 锂硼氢 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以90%的产率得到2,2,3,4,5,6-Hexafluorobenzocyclobuten-1-ol
  参考文献：
  名称：

  用 LiBH4 将全氟苯并环烯酮和其他多氟芳基酮还原为醇

  摘要：

  摘要 在乙醚中用四氢硼酸锂还原多氟苯并环烯-1-酮、全氟-2,3-二氢苯并呋喃-3-酮和全氟二芳基和烷基芳基酮得到相应的醇。全氟 2-甲基-和 2-羟基-2-苯基苯并环丁烯酮的还原伴随着四元环的开环，形成 (全氟-2-乙烯基苯基)甲醇和 [2-(羟甲基)四氟苯基](五氟苯基)甲醇，分别。在全氟苯并环丁烯、茚满和四氢化萘的二羰基衍生物的还原反应中获得了多氟苯并环烯二醇。

  DOI：

  10.1134/s1070428022060045
• 作为产物：
  描述：

  perfluorobenzocyclobutene 在 磺酰氯 、 五氟化锑 、 水 作用下， 反应 168.0h， 生成 全氟苯并环丁烯酮
  参考文献：
  名称：

  全氟和1-氯多氟苯并环烯-1-基阳离子的产生及其相对稳定性

  摘要：

  全氟化的苯并环丁烯，茚满，四氢化萘具有的SbF的治疗5 -SO 2氯2，以及它们的1,1-二氯类似物与的SbF 5，得到1- chloropolyfluorobenzocycloalken -1-基阳离子，其结构，研究了19 F和13 C NMR，并通过水解转化为全氟酮来证实。全氟苯并环丁烯，茚满和四氢萘在过量SbF5中的溶解产生了与其前体平衡的全氟苯并环烯-1-基阳离子。全氟-和1-氯多氟苯并环烯基-1-基阳离子的相对稳定性随脂环族片段尺寸的增加而降低。

  DOI：

  10.1134/s1070428012040100

文献信息

• Reaction of perfluorobenzocycloalkenes with SiO2-SbF5 and skeleton transformations of their carbonyl derivatives in SbF5 medium
  作者：Ya. V. Zonov、V. M. Karpov、V. E. Platonov、Yu. V. Gatilov

  DOI：10.1134/s107042800802005x

  日期：2008.2

  The reaction of perfluorinated benzocyclobutene and tetraline with SiO2-SbF5 led to the formation in a high yield of their mono- and further dicarbonyl derivatives. The monocarbonyl derivatives on heating with SbF5 underwent disproportionation into the corresponding perfluorobenzocycloalkenes and diketones. Both mono- and diketones in the SbF5 medium are liable to suffer skeleton rearrangements yielding five- and six-membered oxygen-containing heterocycles and/or products of the opening of the alicyclic fragment of the substrate, and from the perfluorobenzocyclobutenone compounds were also obtained with a number of carbon atoms greater than that of the initial ketone.

  全氟苯并环丁烯和四氢萘与SiO2-SbF5反应，高产率地生成了它们的一碳和进一步的二碳衍生物。一碳衍生物在加热情况下与SbF5发生歧化反应，生成相应全氟苯并环烯和二酮。在SbF5介质中，一碳和二酮都容易发生骨架重排，生成含氧的五元和六元杂环化合物，以及/或底物中脂环片段的开环产物，并且从全氟苯并环丁烯酮化合物中也获得了碳原子数大于初始酮的产物。
• The aliphatic ring-opening and SNAr substitution in the reactions of perfluorobenzocycloalkenones with K2CO3 in water and methanol
  作者：Yaroslav V. Zonov、Siqi Wang、Victor M. Karpov、Tatyana V. Mezhenkova

  DOI：10.1016/j.jfluchem.2021.109851

  日期：2021.9

  SNAr substitution of fluorine atoms and the five-membered ring-opening are competitive processes; benzocyclobutene-1,2-dione, indan-1,3-dione and tetralin-1,4-dione undergo cleavage of the СO–С(Ar) bond to yield ω-(2,3,4,5-tetrafluorophenyl)-ω-oxoperfluoroalkanoic acids, but only the former reacts selectively, in the other diketones, the СO–С(2) bond cleavage or/and nucleophilic substitution of fluorine

  在与 K 2 CO 3水溶液的反应中，全氟苯并环丁烯-1-酮、3-R-茚满-1-酮和 4-R-萘满-1-酮（R = F，C 2 F 5）经历选择性裂解СO-С(Ar)键在反应混合物酸化后产生（2,3,4,5-四氟苯基）全氟链烷酸；在 C(2) 处带有全氟烷基或全氟苯基的苯并环丁烯-1-酮和茚满-1-酮主要或仅与 СO-С(2) 键的裂解反应，形成 2-取代的四氟苯甲酸；3,3-diethylindan-1-one 产生 5- 和 7-羟基衍生物作为唯一的产物，而对于 3-ethylindan-1-one S N氟原子的Ar取代和五元开环是竞争过程；苯并环丁烯-1,2-二酮、茚满-1,3-二酮和四氢萘-1,4-二酮发生СO-С(Ar)键断裂生成ω-(2,3,4,5-四氟苯基)- ω-氧代全氟链烷酸，但只有前者选择性反应，在其他二酮中，СO-С(2) 键断裂或/和氟原子的亲核取代也发生。全氟苯并环丁烯-1-酮和-1
• 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.
• Oxygen replacement by fluorine in carbonyl derivatives of perfluoroaromatic compounds and isomerization of perfluoroindan-1,3-dione to perfluoro-3-methylenephthalide under the action of HF/SbF5
  作者：Yaroslav V. Zonov、Victor M. Karpov、Vyacheslav E. Platonov、Tatjana V. Rybalova、Yuri V. Gatilov

  DOI：10.1016/j.jfluchem.2006.08.006

  日期：2006.12

  When acted upon by HF/SbF5 at 95 degrees C, carbonyl groups of perfluorinated acetophenone (10), 3,4-dihydronaphthalen-1(2H)-one (8), 2,3-dihydronaphthalene-1,4-dione (9), benzocyclobutenone (6), benzocyclobutenedione (7) and indan-l-one (1) are converted into difluoromethylene groups to give the corresponding perfluoroaromatic products. Perfluoroindan-2-one (5), under the same conditions, is transformed to bis(perfluoroindan-2-yl) ether (21). On heating with HF/SbF5, perfluoroindan-1,3-dione (2) isomerizes into perfluoro-3-methylenephthalide (4) at 95 degrees C, and gives 4,5,6,7-tetrafluoro-3-trifluoromethyl-phthalide (14) at 130 degrees C. Compound 4 in the absence of a solvent dimerizes giving perfluorodispiro[phthalide-3,1 '-cyclobutane-2 ',3 ''-phthalide] (18), and when heated with SbF5 at 130 degrees C, it is converted into perfluoro-3-methylphthalide (3). When acted upon by HF/SbF5 at 95 degrees C, perfluorinated benzoic acid (12) and phthalic anhydride (13) give the corresponding products with trifluoromethyl groups. (c) 2006 Elsevier B.V. All rights reserved.
• Carbonylation of Polyfluorobenzocyclobutenones in a SbF5 Medium
  作者：Ya. V. Zonov、V. M. Karpov、T. V. Mezhenkova

  DOI：10.1134/s1070428019080086

  日期：2019.8

  The carbonylation of perfluoro-2-R-benzocyclobutenones (R = F, CF3, C2F5, C6F5) in a CO-SbF5 system is accompanied by transformations of the four-membered cycle in the substrate to form polyfluorinated 1H-isochromene derivatives. The reaction of perfluoro-2-R-benzocyclobutenes (R = F, CF3, C2F5) with (CF3CO)(2)O or CF3COOH in a SbF5 medium in a sealed ampule involves formation of polyfluorobenzocyclobutenones and their carbonylation under the reaction conditions.