hexafluoro-1,3-indanedione | 58161-60-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: hexafluoro-1,3-indanedione
• 英文别名: hexafluoroindan-1,3-dione；perfluoroindan-1,3-dione；2,2,4,5,6,7-Hexafluoro-1H-indene-1,3(2H)-dione；2,2,4,5,6,7-hexafluoroindene-1,3-dione
• CAS: 58161-60-7
• 化学式: C₉F₆O₂
• 分子量: 254.088
• InChiKey: XYWXKKFHKSXACO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  hexafluoro-1,3-indanedione 在 三氯化铝 、 五氯化磷 、 氯化锑(V) 、 三氟化锑 、 乙酰氯 作用下， 45.0~185.0 ℃ 、9.73 kPa 条件下， 反应 17.0h， 生成 1,1-dichloroperfluoroindan
  参考文献：
  名称：

  Karpov, V. M.; Platonov, V. E.; Chuikov, I. P., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, # 10, p. 1880 - 1888

  摘要：

  DOI：
• 作为产物：
  描述：

  perfluoroindan-1-one 在 五氟化锑 、 三氟乙酸 作用下， 生成 hexafluoro-1,3-indanedione
  参考文献：
  名称：

  Transformation of perfluorinated benzocycloalkenes and alkylbenzenes to their carbonyl derivatives under the action of CF3COOH/SbF5

  摘要：

  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.

  DOI：

  10.1016/j.jfluchem.2007.05.020

文献信息

• 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
• Reduction of Perfluorinated Benzocycloalkenones and Other Polyfluoroaryl Ketones to Alcohols with LiBH4
  作者：S. Wang、D. S. Golokhvastova、Ya. V. Zonov、V. M. Karpov、T. V. Mezhenkova、Yu. V. Gatilov

  DOI：10.1134/s1070428022060045

  日期：2022.6

  The reduction of polyfluorinated benzocycloalken-1-ones, perfluoro-2,3-dihydrobenzofuran-3-one, and perfluorinated diaryl and alkyl aryl ketones with lithium tetrahydridoborate in diethyl ether gave the corre­sponding alcohols. The reduction of perfluorinated 2-methyl- and 2-hydroxy-2-phenylbenzocyclobutenones was accompanied by opening of the four-membered ring with the formation of (perfluoro-2-vinylphenyl)­methanol

  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。
• Karpov,V.M. et al., Journal of Organic Chemistry USSR (English Translation), 1975, vol. 11, p. 2418 - 2429
  作者：Karpov,V.M. et al.

  DOI：——

  日期：——
• 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.
• Formation and skeletal transformations of perfluoroindan-1-one and perfluoroindan-1,3-dione in the reaction of perfluoroindan with SiO2/SbF5
  作者：Yaroslav V. Zonov、Victor M. Karpov、Vyacheslav E. Platonov

  DOI：10.1016/j.jfluchem.2004.09.035

  日期：2005.4

  Perfluoroindan-1-one (2) is obtained in the reaction of perfluoroindan (1) with SiO2/SbF5 at 70 degrees C. Compound 1 heated with SiO2/SbF5 at 130 degrees C and then treated with water, gives 3-hydroxy-perfluoro-3-methylphthalide (4). Ketone 2 is converted, under the action of SbF5 at 130 degrees C, to perfluoro-2-ethylbenzoic acid (9) and disproportionates to compound 1 and perfluoroindan-1,3-dione (3); the latter is transformed to phthalide 4 under the reaction conditions. (c) 2004 Elsevier B.V. All rights reserved.