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2'-Cyclopropylspiro-2'-yl cation | 138260-76-1

中文名称
——
中文别名
——
英文名称
2'-Cyclopropylspiro-2'-yl cation
英文别名
——
2'-Cyclopropylspiro<cyclopropane-3'-norbornan>-2'-yl cation化学式
CAS
138260-76-1
化学式
C12H17
mdl
——
分子量
161.267
InChiKey
YRVIOOFZHRUPQY-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3.18
  • 重原子数:
    12.0
  • 可旋转键数:
    1.0
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.92
  • 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:
    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
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