1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl).2,3-pentane-dione | 74728-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl).2,3-pentane-dione
• 英文别名: perfluoro-4-trifluoromethylpentane-2,3-dione；perfluoro-1-isipropyl-2-methyldiketone；1,1,1,4,5,5,5-Heptafluoro-4-(trifluoromethyl)pentane-2,3-dione
• CAS: 74728-97-5
• 化学式: C₆F₁₀O₂
• 分子量: 294.049
• InChiKey: BOPGPASYCOFVSI-UHFFFAOYSA-N

物化性质

• 沸点：
  53 °C
• 密度：
  1.666±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl).2,3-pentane-dione 在 cesium fluoride 作用下， 反应 1.0h， 以76%的产率得到1,1,1,3,4,4,4-七氟-3-(三氟甲基)-2-丁酮
  参考文献：
  名称：

  Ionic decarboxylation of perfluorinated ?-diketones

  摘要：

  DOI：

  10.1007/bf00959914
• 作为产物：
  描述：

  perfluoro-4-methyl-2-pentene 在 potassium permanganate 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 以53%的产率得到1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl).2,3-pentane-dione
  参考文献：
  名称：

  Partial oxidation of internal fluoroolefins by potassium permanganate

  摘要：

  DOI：

  10.1007/bf00961993

文献信息

• Structure and reactivity of perfluorinated branched α-ketoradicals
  作者：B.L. Tumanskii、E.N. Shaposhnikova、E.A. Avetisyan、R.S. Sterlin

  DOI：10.1016/s0022-1139(98)00319-4

  日期：1999.6

  Fluoroaliphatic hydroxyketoradicals prepared by photochemical reduction of the corresponding α-diketones and (i-C3F7)2C⋅C(O)CF3 react with hydrogen abstraction (according to ESR data). The hydroxyketoradicals are shown to dimerize reversibly, and the dimerization rate decreases in the presence of polyfluorinated alcohols due to the formation of radical–alcohol complexes.

  氟脂hydroxyketoradicals制备由相应的α二酮的光化学还原和（我-C 3 ˚F 7）2 Ç ⋅ C（O）CF 3与夺氢反应（根据ESR数据）。羟基酮三醇可逆地二聚，由于存在自由基-醇配合物，在存在多氟醇的情况下，二聚率降低。
• ESR study of radicals formed by the reduction of α-diketones C(O)C(O)CF3 (R=(CF3)2CF, C6F5, (CF3)3C) with several group I–III metals
  作者：E. N. Shaposhnikova、S. R. Sterlin、S. P. Solodovnikov、N. N. Bubnov、I. V. Stankevich、A. L. Chistyakov、B. L. Tumanskii

  DOI：10.1007/bf02494272

  日期：1998.11

  anions formed by reduction of α-diketones RC(O)C(O)CF3 (R=(CF3)2CF, C6F5, (CF3)3C) with metals (Li, Na, K, Mg, Cd, Zn, Hg, In, and TI) in THF were studied. For R=(CF3)2CF and C6F5, the radical anions are formed ascis-isomers, whereas for R=(CF3)3C,trans-isomers are obtained. Line broadening due to solvation and desolvation of the cation is observed in the latter case. The reduction of α-diketone (CF3)2CFC(O)C(O)CF3

  α-二酮 RC(O)C(O)CF3 (R=( )2CF, C6F5, ( )3C) 与金属 (Li, Na, K, Mg, Cd,研究了 THF 中的 Zn、Hg、In 和 TI)。对于 R=( )2CF 和 ，自由基阴离子形成为顺式异构体，而对于 R=( )3C，获得反式异构体。在后一种情况下观察到由于阳离子的溶剂化和去溶剂化导致的谱线变宽。α-二酮 ( )2CFC(O)C(O) 与 II 族金属（Mg、Cd、Zn）的还原导致自由基对的形成。
• Reactions of 2H-2-oxo-phosphorinanone derivatives and dimethylphosphine oxide with perfluorinated mono- and di-ketones
  作者：A.A. Kadyrov、I. Neda、T. Kaukorat、A. Fischer、P.G. Jones、R. Schmutzler

  DOI：10.1016/0022-1139(94)03162-s

  日期：1995.5

  two isomers 12a and 12b was observed. Reaction of a mixture of 12a and 12b with water led to 2-hydroxy-2-oxo-triazaphosphorinan-4,6-dione (15) and two further perfluorinated products 13 and 14. Dimethylphosphine oxide (3) reacted with perfluoro-isobutylmethyl ketone (4) to give the perfluoroalkyl-substituted α-hydroxyphosphine oxide 16. In contrast to 7-12, compound 16 was shown to contain the P-C-OH

  5,6-苯并-1,3-二甲基-2- ħ -2-氧代- 1,3,2λ 4 -diazaphosphorinan -4-酮（1）和1,3,5-三甲基-2- ħ -2-氧代1,3,5-三氮杂- 2λ 4-磷酸二氢呋喃酮-4,6-二酮（2）与全氟异丁基甲基酮（4），全氟-1-甲基-2-异丙基二酮（5）和全氟-1-甲基-2-正丙基二酮反应（6）由于O-加成反应，通过形成POC键和氢原子从磷迁移到羰基碳原子而产生产物7-12。在2与6的反应中，观察到两个异构体12a和12b的形成。12a和12b的混合物与水的反应产生2-羟基-2-氧代-三氮杂膦酸-4,6-二酮（15）和另外两个全氟化产物13和14。二甲基氧化膦（3）与全氟异丁基甲基酮反应（4）得到全氟烷基取代的α-羟基膦氧化物16。与7-12相反，化合物16显示含有PC-OH片段而不是POC键。1 H，13 C和19 F NMR光谱。所有化合物均通过
• Goerg, Michaela; Dieckbreder, Uwe; Schoth, Ralph-Matthias, Phosphorus, Sulfur and Silicon and the Related Elements, 1997, vol. 124, p. 419 - 424
  作者：Goerg, Michaela、Dieckbreder, Uwe、Schoth, Ralph-Matthias、Kadyrov, Alexander A.、Roeschenthaler, Gerd-Volker

  DOI：——

  日期：——
• Neue Phospholen‐ und Phosphepin‐Derivate aus λ ³ ‐Phosphorverbindungen und Hexafluoraceton oder perfluorierten α‐Diketonen
  作者：Alexander Kadyrov、Ion Neda、Thomas Kaukorat、Ralf Sonnenburg、Axel Fischer、Peter G. Jones、Reinhard Schmutzler

  DOI：10.1002/cber.19961290620

  日期：1996.6

  New Phospholene and Phosphepine Derivatives from λ3‐Phosphorus Compounds and Hexafluoroacetone or Perfluorinated α‐DiketonesThe reaction of the bis(2‐chloroethyl)amino‐substituted benzoxazaphosphorinone 1 with hexafluoroacetone (HFA) proceeds with insertion of the carbonyl group of HFA into the heterocycle of 1 to form the oxazaphosphepinedione 2. Triethyl phosphite (3) and triphenyl phosphite (4) react with the perfluorinated diketones 5 and 6 with formation of the pentaoxyphosphoranes 7–10 containing a dioxaphospholene ring system. The reaction of the (2‐chloroethyl)amino‐ and bis(2‐chloroethyl)amino‐substituted 1,3,5,2‐triazaphosphorinanediones 11–14 with the perfluorinated diketone C2F5C(:O)C(:O)CF3 (15) furnishes spirophosphorane derivatives with the dioxaphospholene ring system, 16 and 17, in two cases only. Compound 1 and 2‐[bis(2‐chloroethyl)‐amino]‐4H‐1,3,2‐benzodioxaphosphorin‐4‐one (18) react with the perfluorinated α‐diketones 5 and 6 with insertion of the diketones into the heterocycle of 1 and 18 with formation of compounds 19–22 containing dioxa‐ and oxazaphosphepinone ring systems. The expected oxidative addition of the diketones to λ3P with formation of spirophosphoranes was not observed. Compounds 19–22 were obtained as mixtures of isomers (19a/b–22a/b). Single crystal X‐ray structure analyses were conducted on 2 and 9. The seven‐membered ring of 2 displays a “tub” conformation, with the O and benzo C atoms lying out of the plane of the other four atoms. The two independent molecules of 9 are similar, but differ in the degree of distortion from trigonal‐bipyramidal geometry of phosphorus.