2-phenyl-2-benzoyladamantane | 133149-77-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-phenyl-2-benzoyladamantane
• 英文别名: Phenyl-(2-phenyl-2-adamantyl)methanone
• CAS: 133149-77-6
• 化学式: C₂₃H₂₄O
• 分子量: 316.443
• InChiKey: CLZMQSIZLIGJFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2',2'-Diphenylspiro[adamantane-2,3'-oxirane] 在 cation-radical orange 9,10-dimethoxy-1,4:5,8-dimethano-1,2,3,4,5,6,7,8-octahydroanthracene*BF₄^(1-) 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以98%的产率得到2-phenyl-2-benzoyladamantane
  参考文献：
  名称：

  Acid Catalysis vs. Electron-Transfer Catalysis via Organic Cations or Cation-Radicals as the Reactive Intermediate. Are These Distinctive Mechanisms?

  摘要：

  Proton transfer to aromatic and olefinic donors (D) lends to the facile interchange of transient carbocations (DH+) and cation-radical (D+.). The same types of cation and cation-radical are reactive intermediates in the acid catalysis and the electron-transfer catalysis of such organic transformations as benzylic coupling, epoxide.-pinacol rearrangements and cis-trans isomerization of stilbenes when they are both carried out under otherwise identical reaction conditions, However, the rapid exchange of diamagnetic cations and paramagnetic cation-radicals blurs the traditional view of sepal ate electrophilic and homolytic processes, and rigorous experimental evidence is required to establish whether acid catalysis and electron-transfer catalysis actually represent distinct mechanistic categories.

  DOI：

  10.3891/acta.chem.scand.52-0114

文献信息

• Catalytic Epoxidation of Hindered Olefins with Dioxygen. Fast Oxygen Atom Transfer to Olefin Cation Radicals from Nitrogen Oxides
  作者：Eric Bosch、Jay K. Kochi

  DOI：10.1021/ja953786n

  日期：1996.1.1

  efficiently converted to epoxides by dioxygen at 25 °C in dichloromethane containing catalytic amounts of nitrogen oxides (NO2, NO+, NO, etc.). Nitrogen dioxide also effects the direct (stoichiometric) epoxidation of the same hindered olefins. Olefin cation radicals are spectrally identified as the first observable intermediate, and separate experiments confirm the facile transfer of an oxygen atom from nitrogen

  受阻烯烃在 25 °C 下通过分子氧在含有催化量氮氧化物（NO2、NO+、NO 等）的二氯甲烷中有效转化为环氧化物。二氧化氮还影响相同受阻烯烃的直接（化学计量）环氧化。烯烃阳离子自由基被光谱鉴定为第一个可观察到的中间体，单独的实验证实氧原子从二氧化氮轻松转移到烯烃阳离子自由基以产生环氧化物。在低温 (-78 °C) 下，添加 1-电子氧化剂如三 (2,4-二溴苯基) 胺阳离子自由基和亚硝 (NO+) 会迅速引发环氧化反应。方案 3 展示了氧化还原变化的完整序列，在受阻烯烃通过阳离子自由基催化转化为环氧化物的过程中，氧化还原变化由氮氧化物介导。
• Electron-transfer reactions of hindered olefins induced by aminium salts.
  作者：Luigi Lopez、Luigino Troisi、Giuseppe Mele

  DOI：10.1016/s0040-4039(00)71233-0

  日期：1991.1

  Hindered olefins 1–6, by reaction with aminium salts, can afford, in relations to the reaction conditions and the peculiar features of the reagents, different reaction products such as dioxetanes, epoxides, ketones, or homoallylic, allylic and vinylic halogenated derivatives.

  通过与铝盐反应，受阻烯烃1-6可以根据反应条件和试剂的特殊特性提供不同的反应产物，例如二氧环乙烷，环氧化物，酮，或均烯丙基，烯丙基和乙烯基卤代衍生物。