5-Phenyl-2-adamantanespirooxirane | 132317-54-5

• 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: 5-Phenyl-2-adamantanespirooxirane
• 英文别名: 1-Phenylspiro[adamantane-4,2'-oxirane]
• CAS: 132317-54-5；132435-77-9；867065-24-5
• 化学式: C₁₇H₂₀O
• 分子量: 240.345
• InChiKey: ZNWVNVNMPCROEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Phenyl-2-adamantanespirooxirane 在 chromium(VI) oxide 、 三氟化硼乙醚 作用下， 以 丙酮 、 苯 为溶剂， 反应 3.1h， 生成 (E)-5-Phenyl-2-adamantanecarboxylic acid
  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
• 作为产物：
  描述：

  5-phenyladamantan-2-one 在 正丁基锂 、 间氯过氧苯甲酸 作用下， 反应 20.5h， 生成 5-Phenyl-2-adamantanespirooxirane
  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

文献信息

• Electronic control of face selection in the capture of radicals
  作者：Vani R. Bodepudi、William J. Le Noble

  DOI：10.1021/jo00006a009

  日期：1991.3

  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.