1H-pentadecafluoroadamantane | 54767-15-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 1H-pentadecafluoroadamantane
• 英文别名: 1-hydropentadecafluoroadamantane；1-Hydropentadecafluoradamantan；1,2,2,3,4,4,5,6,6,8,8,9,9,10,10-Pentadecafluoroadamantane
• CAS: 54767-15-6
• 化学式: C₁₀HF₁₅
• 分子量: 406.094
• InChiKey: LNRSUICBKASFRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  1H-pentadecafluoroadamantane 在 甲基锂 、 碘 作用下， 以 乙醚 为溶剂， 反应 0.25h， 生成 1-iodo-F-adamantane
  参考文献：
  名称：

  Synthesis of lithio-F-adamantanes: the first documented fluorine-19 NMR spectrum of a perfluoroalkyllithium and the rearrangement of 2-lithio-F-adamantane to 1-lithio-F-adamantane

  摘要：

  The synthesis, F-19-NMR, and reactions of a very stable diamondoid perfluoroalkyllithium, 1-lithio-F-adamantane, and the observation of an unusual rearrangement of 2-lithio-F-adamantane to 1-lithio-F-adamantane are reported.

  DOI：

  10.1021/jo00060a007
• 作为产物：
  描述：

  金刚烷 在 fluorine 作用下， 生成 1H-pentadecafluoroadamantane
  参考文献：
  名称：

  Synthesis of structurally unusual fluorocarbons by direct fluorination

  摘要：

  DOI：

  10.1021/ja00836a008

文献信息

• Molecular structure of perfluoroadamantane from gas-phase electron diffraction
  作者：István Hargittai、Jon Brunvoll、Takaaki Sonoda、Takashi Abe、Hajime Baba

  DOI：10.1016/s0022-2860(97)00412-2

  日期：1998.4

  The following bond lengths (r(g)) and bond angles have been determined for perfluoroadamantane from gas-phase electron diffraction: C-C 1.560 +/- 0.003, C(F(2))-F 1.340 +/- 0.005, C(F)-F 1.363 +/- 0.010 Angstrom, CC(F(2))C 107.7 +/- 0.9, CC(F)C 110.3 +/- 0.4, FC(F(2))F 106.9 +/- 0.4, C(F(2))CF 108.6 +/- 0.4 and C(F)CF 110.5 +/- 0.2 degrees. Perfluorination is found to expand the adamantane cage, characterized by a 0.02 Angstrom lengthening of the C-C bonds. (C) 1998 Elsevier Science B.V.
• Aerosol fluorination of 1-chloroadamantane, 2-chloroadamantane, and methyl 1-adamantylacetate: a novel synthetic approach to 1- and 2-substituted hydryl-, methyl-, and (difluoromethyl-F-adamantanes
  作者：James L. Adcock、Huimin Luo、Sharique S. Zuberi

  DOI：10.1021/jo00043a039

  日期：1992.8
• Photochemical Reduction of F-Adamantyl Halides: A Facile Synthesis of Hydrylfluorocarbons from Chlorofluorocarbons
  作者：James L. Adcock、Huimin Luo

  DOI：10.1021/jo00084a032

  日期：1994.3

  1-Chloro- and 2-chloro-F-adamantanes, 1,2- and 1,3-dichioro-F-adamantanes, 1,3,5-trichloro-F-adamantane, 1,3,5,7-tetrachloro-F-adamantane, 1-bromo-F-adamantane, and 1-iodo-F-adamantane dissolved in CFCl3 are conveniently dehalogenated in the presence of methanol, hexane, or other hydrogen donor cosolvents by ultraviolet irradiation. The reactions are very clean with isolated yields in the range of 80%-90%. Generally, irradiation times increase when large batches of material are photolyzed and when the less reactive secondary F-adamantyl chlorides are reduced. By controlling the irradiation time, polychloro-F-adamantanes can be reduced in a stepwise manner. Only free-radical, not ionic, products are isolated. A possible mechanism for this photochemical reduction is discussed.
• Functional group transformation of perfluoroadamantane derivatives
  作者：Koichi Murata、Shu-Zhong Wang、Yoshitomi Morizawa、Kazuya Oharu

  DOI：10.1016/j.jfluchem.2006.06.001

  日期：2006.8

  An adarnantane skeleton, having rigid structure, has been used for a thermally stable and/or anti-etching material. It is expected to be a material having good optical properties, if fluorine atoms are introduced into the skeleton. Thus, the investigation concerning the functional group transformation of perfluoroadamantanecarboxylic acid derivatives was performed to develop the methods for introduction of perfluoroadamantyl group into molecules. Their unique reactivities are also discussed. (c) 2006 Elsevier B.V. All rights reserved.
• EP1942091
  申请人：——

  公开号：——

  公开（公告）日：——