1-tridecafluorohexylnaphthalene | 93697-17-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-tridecafluorohexylnaphthalene
• 英文别名: 1-perfluoro-n-hexylnaphthalene；1-(perfluorohexyl)naphthalene；1-(Tridecafluorohexyl)naphthalene；1-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)naphthalene
• CAS: 93697-17-7
• 化学式: C₁₆H₇F₁₃
• 分子量: 446.211
• InChiKey: QQYGCXVOZCUYBA-UHFFFAOYSA-N

物化性质

• 沸点：
  83-84 °C(Press: 0.15 Torr)
• 密度：
  1.516±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  萘 、 全氟己基碘烷 在 FeCl₂(2,2'-dipyridyl) 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到1-tridecafluorohexylnaphthalene
  参考文献：
  名称：

  Iron-catalyzed electrochemical C–H perfluoroalkylation of arenes

  摘要：

  描述了一种新的铁催化的反应，用于偶联全氟烷基碘化物和芳香基底物。

  DOI：

  10.1039/c5dt03009a

文献信息

• Synthesis of functionalized long-chain perfluoroalkanes from methyl halodifluoroacetates: a process of difluorocarbene insertion intocopper-carbon bonds
  作者：De-Bao Su、Jian-Xing Duan、An-Juan Yu、Qing-Yun Chen

  DOI：10.1016/s0022-1139(00)80465-0

  日期：1993.11

  organic halides in the presence of KF and catalytic amounts of CuI at 80–120 °C for 3–8 h in DMF gave long-chain perfluoroalkylated compounds which are considered to be former by the insertion of CF:2into carbon-copper bonds.

  在KF存在下，用有机卤化物处理XCF 2 CO 2 Me（X = Cl，Br），并在DMF中于80–120°C催化量的CuI处理3–8 h，得到长链全氟烷基化化合物，认为该化合物通过在碳-铜键中插入CF：2来形成前一键。
• Triarylamines as catalytic donors in light-mediated electron donor–acceptor complexes
  作者：Durbis J. Castillo-Pazos、Juan D. Lasso、Ehsan Hamzehpoor、Jorge Ramos-Sánchez、Jan Michael Salgado、Gonzalo Cosa、Dmytro F. Perepichka、Chao-Jun Li

  DOI：10.1039/d2sc07078b

  日期：——

  Recently, photochemistry of Electron Donor–Acceptor (EDA) complexes employing catalytic amounts of electron donors have become of interest as a new methodology in the catalysis field, allowing for decoupling of the electron transfer (ET) from the bond-forming event. However, examples of practical EDA systems in the catalytic regime remain scarce, and their mechanism is not yet well-understood. Herein

  最近，使用催化量电子供体的电子供体-受体 (EDA) 复合物的光化学作为催化领域的一种新方法引起了人们的兴趣，它允许电子转移 (ET) 从成键事件中解耦。然而，催化体系中实际 EDA 系统的例子仍然很少，而且它们的机制还没有得到很好的理解。在此，我们报告了三芳基胺和 α-全氟磺酰基苯丙酮试剂之间的 EDA 络合物的发现，该络合物在 pH 和氧化还原中性条件下在可见光照射下催化芳烃和杂芳烃的 C-H 全氟烷基化。我们使用 EDA 复合物的详细光物理特性、生成的三芳基胺自由基阳离子及其周转事件阐明了该反应的机制。
• Redox system for perfluoroalkylation of arenes and α-methylstyrene derivatives using titanium oxide as photocatalyst
  作者：Mari Iizuka、Masato Yoshida

  DOI：10.1016/j.jfluchem.2009.07.010

  日期：2009.10

  Photoirradiation of titanium oxide (TiO2) excites the electrons from the valence band to the conduction band, leaving holes in the valence band. Using these holes and electrons, it is possible to perform one-electron oxidations and reductions. We developed a method for the photocatalytic perfluoroalkylation of aromatic rings such as benzene and its derivatives, naphthalene and benzofuran with perfluoroalkyl iodide by the combination of reduction and oxidation reactions with TiO2. Perfluoroalkyl iodide was reduced to a perfluoroalkyl radical by the excited electrons in the conduction band of TiO2, and the resulting radical reacted with an aromatic ring to form an arenium radical that was successively oxidized to a cation by the holes in the valence band of TiO2. Similarly, the photocatalytic reaction of alpha-methylstyrene with perfluoroalkyl iodide afforded perfluoroalkylated alpha-methylstyrene, in which the perfluoroalkyl group is on a methyl carbon. (C) 2009 Elsevier B.V. All rights reserved.
• Fluoroalkylation of aromatic compounds with per(poly)fluoroalkyl chlorides initiated by sodium dithionite in DMSO
  作者：Xiao-Ting Huang、Zheng-Yu Long、Qing-Yun Chen

  DOI：10.1016/s0022-1139(01)00442-0

  日期：2001.10

  Treatment of electron-rich aromatic and heteroaromatic. compounds with per(poly)fluoroalkyl chlorides in the presence of sodium dithionite in DMSO gives the corresponding fluoroalkylated products in moderate to good yields. The structures and yields of products depend mainly on the position and electron-donating ability of the substituents on the aromatic compounds. (C) 2001 Elsevier Science B.V. All rights reserved.
• Polyfluoroalkylation of bromoaromatic compounds via perfluoroalkylcopper intermediates
  作者：Grace J. Chen、Christ Tamborski

  DOI：10.1016/s0022-1139(00)82940-1

  日期：1989.5