hexafluoro-1,4-naphthoquinone | 1024-60-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: hexafluoro-1,4-naphthoquinone
• 英文别名: Hexafluor-naphthochinon-(1,4)；Hexafluornaphthochinon；2,3,5,6,7,8-Hexafluoronaphthalene-1,4-dione
• CAS: 1024-60-8
• 化学式: C₁₀F₆O₂
• mdl: MFCD00168594
• 分子量: 266.099
• InChiKey: ODOWBQJUWIEMDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  0
• 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：
  8

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  hexafluoro-1,4-naphthoquinone 在 氯化亚砜 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 124.0h， 生成 N,N-diethyl-6-(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)hexanamide
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of polyfluorinated 1,4-naphthoquinones containing amino acid substituents

  摘要：

  New conjugates of polyfluorinated 1,4-naphthoquinone core with amino acid fragments were synthesized by the reactions of hexafluoro-1,4-naphthoquinone (1) with ethyl aminoacetate, glycine, 3-aminopropanoic, 4-aminobutanoic, and 6-aminohexanoic acids. In all the cases, the quinone 1-aminodefluorination on the 2-position occurred to give ethyl (3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)aminoacetate (2), (3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)aminolacetic (3), 3-[(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]propanoic (4), 4-[(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]butanoic (5), and 6-[(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]hexanoic acid (6), respectively. A possibility to further modify a carboxylic function of omega-[5,6,7,8-tetrafluoro-1,4-naphthoquinon-2-yl]aminocarboxylic acids was demonstrated by transformation of acids 3 and 5 into the corresponding acyl chlorides 10 and 12 followed by their in situ conversion into N,N-diethylamides 13 and 14 or ethyl esters 15 and 16. Upon the analogous treatment of acid 4 the primary generated acyl chloride 11 underwent an intramolecular N-acylation to yield 2,5,6,7,8-pentafluoro-3-(2-oxopyrrolidin-1-yl)naphthalene-1,4-dione (17) which was smoothly diethylaminodefluorinated at the 3-position to afford 2-(2-oxopyrrolidin-1-yl)-3-diethylamino-5,6,7,8-tetrafluoronaphthalene-1,4-dione (18). The cytotoxicity evaluation of twelve new quinones in human myeloma, human mammary adenocarcinoma, human hepatocellular carcinoma HepG2 epithelial tumor cells, normal mouse fibroblasts and Chinese hamster Ag 17 cells as well as their mutagenic and antioxidant properties in a Salmonella tester strain was performed. All the compounds effectively suppressed the growth of three lines of tumor cells. These data together with the better cytotoxic effect against cancer cells compared to normal mammalian cells, the bacterial cells protection against spontaneous and H2O2-dependent mutagenesis, and lower general toxicity toward different cells, reveal quinones 2, 13, 15, 16, and 18 as best inhibitors of tumor cells growth among the tested substances. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.04.014
• 作为产物：
  描述：

  八氟萘 在 hydroxide 作用下， 生成 hexafluoro-1,4-naphthoquinone
  参考文献：
  名称：

  The interaction of polyfluoroaromatic compounds with oxygen containing radicals

  摘要：

  DOI：

  10.1016/s0022-1139(00)83379-5

文献信息

• Catalytic Defluorination of Perfluorinated Aromatics under Oxidative Conditions Using N-Bridged Diiron Phthalocyanine
  作者：Cédric Colomban、Evgenij V. Kudrik、Pavel Afanasiev、Alexander B. Sorokin

  DOI：10.1021/ja505437h

  日期：2014.8.13

  [(Pc)(F)Fe(IV)(μ-N)Fe(IV)(F)(Pc(+•))], which was isolated and characterized by UV-vis, EPR, (19)F NMR, Fe K-edge EXAFS, XANES, and Kβ X-ray emission spectroscopy, ESI-MS, and electrochemical techniques. A wide range of per- and polyfluorinated aromatics (21 examples), including C6F6, C6F5CF3, C6F5CN, and C6F5NO2, were defluorinated with high conversions and high turnover numbers. [(Pc)Fe(III)(μ-N)Fe(IV)(Pc)]

  碳氟键是有机化学中最强的单键，这使得通常与有机金属和还原方法相关的活化和裂解特别困难。我们在此描述了在温和条件下（氢）催化的多氟和全氟芳烃的有效脱氟，由 μ-硝基二铁酞菁配合物 [(Pc)Fe(III)(μ-N)Fe(IV)(Pc)] 催化。过氧化物作为氧化剂，接近环境温度）。该反应通过与氟化物轴向配体 [(Pc)(F)Fe(IV)(μ-N)Fe(IV)(F)(Pc(+•) )]，通过 UV-vis、EPR、(19)F NMR、Fe K-edge EXAFS、XANES 和 Kβ X 射线发射光谱、ESI-MS 和电化学技术对其进行分离和表征。包括 C6F6、C6F5CF3、C6F5CN 和 C6F5NO2 在内的各种全氟和多氟芳烃（21 个例子）都以高转化率和高转化率脱氟。固定在碳载体上的 [(Pc)Fe(III)(μ-N)Fe(IV)(Pc)] 在水中的非均相脱氟中显示出更高的催化活性，每个催化剂分子提供高达
• Aromatic fluoroderivatives. XCVI. Reactions of polyfluoroaromatic compounds with salts of the fluorochloronium and fluorobromonium
  作者：V.V. Bardin、G.G. Furin、G.G. Yakobson

  DOI：10.1016/s0022-1139(00)81280-4

  日期：1983.7

  cations to give fluorinated derivatives of 1,4-cyclohexadiene and 1-aza-1,3-cyclohexadiene respectively. In the absence of fluorine anion acceptors, ClF3, BrF3 and BrF5 are less reactive in these reactions than salts of the HalF+n cations.

  苯，萘和吡啶的多氟化衍生物与二氟氯鎓ClF + 2，二氟溴BrF + 2和四氟溴BrF + 4阳离子的盐反应，分别得到1,4-环己二烯和1-氮杂-1,3-环己二烯的氟化衍生物。在不存在氟阴离子受体的情况下，与HalF + n阳离子的盐相比，ClF 3，BrF 3和BrF 5在这些反应中的反应性较低。
• The preparation and characterization of radical cation salts derived from perfluorobenzene, perfluorotoluene, and perfluoronaphthalene
  作者：T. J. Richardson、F. L. Tanzella、Neil. Bartlett

  DOI：10.1021/ja00276a039

  日期：1986.8

  c/sub 0/ = 18.57 (s) A V = 1270 A, Z = 4. Salts derived from the monocyclic perfluoro aromatics are thermally unstablemore » but can be kept below -15 /sup 0/C. The perfluoronaphthalene salts are indefinitely stable at room temperatures. All hydrolyze rapidly. The products of thermal decomposition of the hexafluoroarsenates of the monocyclic cation salts parallel the products of the attack by F/sup

  盐 C/sub 6/F/sub 6//sup +/AsF/sub 6//sup -/、C/sub 6/F/sub 5/CF/sub 3//sup +/AsF/sub 6/ /sup -/ 和 C/sub 10/F/sub 8//sup +/AsF/sub 6//sup -/ 可以通过适当的全氟芳族分子与 O/sub 2//sup + 的电子氧化来制备/AsF/sub 6//sup -/. 其他 O/sub 2//sup +/ 盐可以与氧化性更强的过渡金属六氟化物类似地使用，但后者的盐比它们的 AsF/sub 6//sup -/ 亲戚更不稳定。C/sub 6/F/sub 6//sup +/AsF/sub 6//sup -/ 是一种方便的电子氧化剂，因为反应中残留的物质在室温下分解为挥发性产物。C/sub 6/F/sub 6/AsF/sub 6/ 和 C/sub 10/F/sub 8/AsF/sub
• Synthesis of novel phosphonium betaines and bis-betaines derived from hexafluoro-1,4-naphthoquinone
  作者：S.I. Zhivetyeva、E.V. Tretyakov、I.Yu. Bagryanskaya

  DOI：10.1016/j.jfluchem.2017.11.010

  日期：2018.2

  bis-phenylphosphanes with structure Ph2P(CH2)nPPh2 (where n = 1–5) and Et2P(CH2)2PEt2 in various solvents (anhydrous C6H6, aq. C6H6, aq. dioxane, aq. DMSO, or MeOH) were investigated. It was shown that the use of aqueous dioxane and DMSO leads to target products of phosphanodefluorination (i.e., phosphorus-containing betaines and bis-betaines) with high yields. We found that the betaines upon purification

  六氟-1,4-萘醌的反应与磷为中心的双- phenylphosphanes与结构博士2 P（CH 2）Ñ PPH 2（其中n = 1-5）和Et 2 P（CH 2）2 PET 2在各种溶剂中（无水C 6 H 6，水溶液C 6 H 6，aq。二恶烷水溶液 研究了DMSO或MeOH）。结果表明，使用二恶烷水溶液和DMSO可以高收率地实现磷阳极氟化的目标产物（即，含磷的甜菜碱和双甜菜碱）。我们发现，通过薄层色谱法纯化后的甜菜碱经历了各种转化，例如环收缩（因此产生了新型的多氟茚满）或在氟化的1,4-萘醌的C O键处添加了丙酮分子。根据X射线衍射分析，所有获得的甜菜碱的晶体堆积中都存在分子间的F⋯π相互作用。相互作用的特征是从3.151（5）到3.831（2）Å的短距离F⋯Cg（其中Cg是π系统的质心）。
• 2-DIETHYLAMINOVINYL DERIVATIVES OF HALOGENATED 1,4-QUINONES: SYNTHETIC AND STRUCTURAL ASPECTS
  作者：S. I. Zhivetyeva、I. A. Zayakin、I. Yu. Bagryanskaya、E. V. Tretyakov

  DOI：10.1134/s0022476620080107

  日期：2020.8

  Diethylaminovinyl derivatives of halogenated 1,4-quinones (enaminoquinones) are produced by the interaction of halogenated 1,4-quinones with N,N-diethyl-N-vinylamine obtained in situ from Et2NH and MeCHO. Molecular and crystal structures of enaminoquinones halogenated in the quinone fragment are determined. It is shown that in the solid phase, atoms of the entire push-pull system of enaminoquinones

  卤化 1,4-醌（烯氨基醌）的二乙基氨基乙烯基衍生物是通过卤化 1,4-醌与从 Et2NH 和 MeCHO 原位获得的 N,N-二乙基-N-乙烯基胺相互作用产生的。确定了醌片段中卤化的烯氨基醌的分子和晶体结构。结果表明，在固相中，烯氨基醌的整个推拉系统的原子实际上位于一个平面内。