2-chloroperfluoroadamantane | 142422-09-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 2-chloroperfluoroadamantane
• 英文别名: 2-chloro-F-adamantane；2-Chloro-1,2,3,4,4,5,6,6,7,8,8,9,9,10,10-pentadecafluoroadamantane
• CAS: 142422-09-1
• 化学式: C₁₀ClF₁₅
• 分子量: 440.539
• InChiKey: WQTNZFIPLDYRPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 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：

  2-chloroperfluoroadamantane 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 反应 22.0h， 以54%的产率得到2-hydrylperfluoroadamantane
  参考文献：
  名称：

  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

  摘要：

  DOI：

  10.1021/jo00043a039
• 作为产物：
  描述：

  2-氯金刚烷 在 fluorine 作用下， 以 1,1,2-三氯乙烷 为溶剂， 反应 3.0h， 以50.7%的产率得到2-chloroperfluoroadamantane
  参考文献：
  名称：

  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

  摘要：

  DOI：

  10.1021/jo00043a039

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.
• Syntheses of F-adamantyl polychlorides and F-1-norbornyl chloride: the first documented 1,3-chlorine shift
  作者：James L. Adcock、Huimin Luo

  DOI：10.1021/jo00059a018

  日期：1993.3

  1,2-Dichloro-F-adamantane, 1,3-dichloro-F-adamantane, 1,3,5-trichloro-F-adamantane, 1,3,5,7-tetrachloro-F-adamantane, and 1-chloro-F-norbornane have been synthesized by aerosol direct fluorination from their corresponding hydrocarbons for the first time. All compounds have been characterized by F-19 NMR, FT-IR, mass spectrometry, and elemental analysis. The aerosol direct fluorination of 2,2-dichloroadamantane produced a mixture of two dichloro-F-adamantanes plus a trace amount of 2-chloro-F-adamantane (chlorine loss product). The mixture of dichlorinated products indicated that chlorine shifts during this aerosol direct fluorination had occurred. The high probability of a 1,3-chlorine shift versus sequential 1,2-chlorine shifts or intermolecular chlorine redistribution is discussed.
• 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