Decafluorobenzil | 19555-07-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: Decafluorobenzil
• 英文别名: decafluorobenzyl；perfluoro benzil；Decafluorbenzil；Perfluorbenzil；Bis(pentafluorophenyl)ethane-1,2-dione；1,2-bis(2,3,4,5,6-pentafluorophenyl)ethane-1,2-dione
• CAS: 19555-07-8
• 化学式: C₁₄F₁₀O₂
• 分子量: 390.137
• InChiKey: DIDVLGUIGXFFDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  Decafluorobenzil 在 高氯酸四乙基铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 全氟二苯甲酮
  参考文献：
  名称：

  Preparative Electrochemical Reduction of Decafluorobenzil

  摘要：

  Preparative electrochemical reduction of decafluorobenzil in DMF on a platinum electrode at the potential of the first peak afforded decafluorobenzophenone as the principal product. The reaction mixture lacked products of hydrodefluorination of the decafluorobenzil or of its reduction at the C=O group.

  DOI：

  10.1023/b:rujo.0000045893.52310.94
• 作为产物：
  描述：

  五氟苯锂 在 HCl 作用下， 以 乙醚 、 正己烷 为溶剂， 生成 Decafluorobenzil
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.4, 1.3.3.8, page 33 - 59

  摘要：

  DOI：

文献信息

• Nitroxide chemistry. Part I. Reactions of bistrifluoromethyl nitroxide with acetylene, 3,3,3-trifluoropropyne, perfluoropropyne, perfluorobut-2-yne, perfluorodiphenylacetylene, and glyoxal
  作者：R. E. Banks、R. N. Haszeldine、T. Myerscough

  DOI：10.1039/j39710001951

  日期：——

  4-diazapentane) the following products were formed from reactions between bistrifluoromethyl nitroxide and the acetylenes named in parentheses: perfluoro-[3,3-bis-(dimethylamino-oxy)butan-2-one], perfluoro-(3-dimethylamino-3-dimethylamino-oxybutan-2-one), and perfluorobiacetyl (from perfluorobut-2-yne); perfluorobenzil (from perfluorodiphenylacetylene); perfluoro-[2,2-bis(dimethylamino-oxy)propanoyl] fluoride

  除全氟-（2,4-二甲基-3-氧杂-2,4-二氮杂戊烷）外，还由双三氟甲基硝基氮氧化物与括号中所述的乙炔之间的反应形成以下产物：全氟-[3,3-双-（二甲基氨基） -氧）丁-2-酮]，全氟-（3-二甲基氨基-3-二甲基氨基-氧丁-2-酮）和全氟联乙酰基（来自全氟丁-2-炔）；全氟苯甲醚（来自全氟二苯乙炔）; 全氟-[2，2-双（二甲基氨基-氧基）丙酰基]氟化物，全氟-（2-二甲基氨基-2-二甲基氨基-氧基丙酰基）氟化物和全氟丙酮酰氟（来自全氟丙炔）；神经网络-双三氟甲基羟胺和双-（双三氟甲基氨基-氧基）双三氟甲基氨基-氧羰基甲烷（来自乙炔）；和3,3-双-（双三氟甲基氨基-氧基）-1,1,1-三氟丙烷-2-酮和3-双三氟甲基氨基-3-双三氟甲基氨基-氧基-1,1,1-三氟丙烷-2-酮（从1， 1,1-三氟丙炔）。讨论了这些转换的可能机制。全氟丁-2-炔与全氟-（2,4-二甲基-3-氧杂-2
• Polyfluoroaryl organometallic compounds. Part XV. Synthesis and rearrangement of polyhalogenoaryl α-diketones
  作者：R. D. Chambers、M. Clark、D. J. Spring

  DOI：10.1039/p19720002464

  日期：——

  dimethyl or diethyl oxalate. Decafluorobenzil undergoes fast base-catalysed rearrangement to the benzilic acid or ester and it is proposed that the transition-state in the process has considerable benzenide character. Attempts to synthesise perfluorophenanthrene-9,10-quinone. by an analogous route, led only to products of rearrangement.

  十氟苯和十氯苯是通过相应的芳基锂与草酸二甲酯的反应制得的，表明该过程涉及加合物的中间体。不对称的苯甲醚C 6 F 5 ·CO·-CO·C 6 H 5和C 6 H 5 ·CO·CO·C 6 Cl 5通过将不同的芳基-锂顺序地加到草酸二甲酯或二乙酯中可得到α-己内酰胺。十氟苯经过碱的快速催化重排，生成苯甲酸或酯，并提出该过程中的过渡态具有显着的苯甲酰胺特性。尝试合成全氟菲-9,10-醌。通过类似的途径，只会导致产品重排。
• Polyfluoroaryl organometallic compounds. Part XVI. Reactions of organolithium compounds with halogenated benzils
  作者：R. D. Chambers、M. Clark

  DOI：10.1039/p19720002469

  日期：——

  Reactions of alkyl- or aryl-lithiums with decafluorobenzil gave adducts which undergo rapid pentafluorophenyl migration. A variety of products were obtained after hydrolysis, depending on the lithio-derivative used: ketoalcohols, a benzo[b]furan derivative (from C6F5Li), and bis(pentafluorophenyl)methyl pentachlorobenzoate (from C6Cl5Li). The mechanisms of these processes are discussed. Some analogous

  烷基锂或芳基锂与十氟苯甲酰的反应生成加合物，该加合物经历了快速的五氟苯基迁移。水解后，根据所使用的硫代衍生物，可得到多种产品：酮醇，苯并[ b ]呋喃衍生物（来自C 6 F 5 Li）和双（五氟苯基）五氯苯甲酸二甲酯（来自C 6 Cl 5 Li）。 。讨论了这些过程的机制。描述了一些类似的苯甲酰反应用于比较，并研究了这些过程中各组的相对迁移能力。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.4, 1.3.3.8, page 33 - 59
  作者：

  DOI：——

  日期：——
• Synthesis of new 2,3-perfluoroalkyl- and perfluoroaryl-1,4-diazabutadienes (α-diimines)
  作者：Bruce N. Diel、Peter J. Deardorff、Catherine M. Zelenski

  DOI：10.1016/s0040-4039(99)01692-5

  日期：1999.12

  Reaction of either decafluorobenzil or perfluorobiacetyl with two equivalents of Li[N(SiMe3)(2)], followed by quenching with ClSiMe3, provides N,N'-bis(trimethylsilyl)-1,2-bis(pentafluorophenyl)ethanediimine 1 and N,N'-bis(trimethylsilyl)- 1,1,1,4,4,4-hexafluoro-2,3-butanediimine 2, respectively. These represent the first examples of perfluoroalkyl- and perfluoroaryl-substituted diazabutadienes. Both compounds have been characterized based on C-13 NMR, IR, elemental analysis and, for 1, single crystal X-ray crystallographic structure determination. Compound 1 crystallizes in the C2/c space group, with a=20.3203(9) X, b=6.0758(3) X, c=19.7948(9) X, alpha=90 degrees, beta=106.2903(7)degrees, gamma=90 degrees. (C) 1999 Elsevier Science Ltd. All rights reserved.