1-bromo-F-adamantane | 148138-95-8

• 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: 1-bromo-F-adamantane
• 英文别名: 1-Bromo-2,2,3,4,4,5,6,6,7,8,8,9,9,10,10-pentadecafluoroadamantane
• CAS: 148138-95-8
• 化学式: C₁₀BrF₁₅
• 分子量: 484.99
• InChiKey: GUMKVWXWWDFEPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 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：

  1-bromo-F-adamantane 在 甲醇 作用下， 以 一氟三氯甲烷 为溶剂， 反应 0.5h， 生成 1H-pentadecafluoroadamantane
  参考文献：
  名称：

  Photochemical Reduction of F-Adamantyl Halides: A Facile Synthesis of Hydrylfluorocarbons from Chlorofluorocarbons

  摘要：

  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.

  DOI：

  10.1021/jo00084a032
• 作为产物：
  描述：

  1H-pentadecafluoroadamantane 在 甲基锂 、 溴 作用下， 以 乙醚 为溶剂， 反应 0.25h， 生成 1-bromo-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

文献信息

• 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.
• 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
  作者：James L. Adcock、Huimin Luo

  DOI：10.1021/jo00060a007

  日期：1993.4

  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.