2-Phenyl-4-methybicyclo<3.2.1>oct-3-en-2-yl cation | 138260-78-3

• 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: 2-Phenyl-4-methybicyclo<3.2.1>oct-3-en-2-yl cation
• CAS: 138260-78-3
• 化学式: C₁₅H₁₇
• 分子量: 197.3
• InChiKey: USIKLXGXQXNRIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  2'-Phenylspiro-2'-ol 在 五氟化锑 、 氟磺酸 作用下， 以 氯氟磺酰 为溶剂， 生成 2-Phenyl-4-methybicyclo<3.2.1>oct-3-en-2-yl cation
  参考文献：
  名称：

  Stable carbocations. 283. Carbon-13 NMR spectroscopic investigation of tertiary spiro[cyclopropane-3'-norbornan]-2'-yl cations and their rearrangements

  摘要：

  2'-Methylspiro[cyclopropane-3'-norbornan]-2'-yl (9), 2'-phenylspiro[cyclopropane-3'-norbornan]-2'-yl (10), and 2-cyclopropylspiro[cyclopropane-3'-norbornan]-2'-yl (11) cations were prepared from the corresponding alcohols with Magic Acid (1:1 SbF5 + FSO3H) at low temperatures and characterized by C-13 NMR spectroscopy. Cation 11 is extremely stable up to -20-degrees-C. Cation 10 rearranges to the 2-phenyl-4-methylbicyclo[3.2.1]oct-3-en-2-yl cation (13) at about -70-degrees-C. The cation 9, and its rearranged isomer 2,4-dimethylbicyclo[3.2.1]oct-3-en-2-yl cation (12), exist in an 1:1 ratio even at -90-degrees-C. The chemical shift assignments were aided by ab initio IGLO calculations. The study shows the overwhelming delocalizing ability of the 3-spirocyclopropyl group over C1-C6 sigma-bond participation. The latter nonclassical sigma-participation, however, was shown to persist to some extent even in the tertiary 2-norbornyl cations.

  DOI：

  10.1021/jo00030a016