(E)-2-Bromo-5-phenyl-2-(2,2,2-trichloroethyl)adamantane | 132317-58-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-Bromo-5-phenyl-2-(2,2,2-trichloroethyl)adamantane
• CAS: 132317-58-9；132435-80-4
• 化学式: C₁₈H₂₀BrCl₃
• 分子量: 422.62
• InChiKey: WTHPOFOKTMUFFV-CQVKHZRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.66
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  5-phenyladamantan-2-one 在 正丁基锂 、 偶氮二异丁腈 作用下， 反应 30.5h， 生成 (E)-2-Bromo-5-phenyl-2-(2,2,2-trichloroethyl)adamantane
  参考文献：
  名称：

  Electronic control of face selection in the capture of radicals

  摘要：

  A simple procedure is described which leads to the pure epimeric 2-(5-phenyl)adamantanecarboxylic acids E-1 and Z-1. Both acids upon treatment with bromine and mercuric oxide in carbon tetrachloride undergo the Hunsdiecker reaction to give the same mixture of E- and Z- 2-bromo-5-phenyladamantanes 4. 5-Phenyl-2-methyleneadamantane 6 undergoes reaction with bromotrichloromethane to give two diastereomeric adducts. In both instances, the major isomer results from the abstraction of a bromine atom by the zu face of the intermediate 5-phenyl-2-adamantyl radicals. The results mesh with other examples of face selection which we have previously ascribed to transition-state hyperconjugation. An additional case (hydride shift in a carbocation) was encountered in this work, as well as one apparent exception: the oxirane formation from adamantanone and sulfonium ylids. That result is attributed to thermodynamic control of the initial addition step.

  DOI：

  10.1021/jo00006a009