1,3,6,8-tetracyclohexylpyrene | 78751-91-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1,3,6,8-tetracyclohexylpyrene
• CAS: 78751-91-4
• 化学式: C₄₀H₅₀
• 分子量: 530.837
• InChiKey: BQURVFKYBWSXCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.2
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3,6,8-tetracyclohexylpyrene 在 氯氟磺酰 、 五氟化锑 、 氟磺酸 作用下， 生成 1,3,6,8-tetracyclohexylpyrene dication
  参考文献：
  名称：

  Oxidation of sterically crowded alkyl(cycloalkyl)pyrenes. Persistent dications in SbF5/SO2ClF and radical cations in FSO3H/SO2

  摘要：

  Sterically crowded alkylpyrenes 2-7 undergo two-electron oxidation with SbF5/SO2ClF (or SbF5.FSO3H (9:1)/SO2ClF) to give persistent alkylpyrene dications. In agreement with the charge distribution pattern observed in the parent pyrene dication and with semiempirical calculations (AM1) on isomeric monoisopropylpyrenes dications; the deshielding order C(alpha) > C(alphabeta) > C(beta) was found in their carbon-13 NMR spectra regardless of the number and position of the alkyl substituents. In most cases, the observed DELTAdelta13C for the aromatic ipso-carbon signals of the alkylpyrenium dications relative to those of 1(+2) were slightly larger than expected for a normal substituent effect in the alkylpyrene precursors. Only minor changes (DELTAdelta13C) in the unsubstituted positions were observed, except for the ring carbons in highly crowded locations for which a noticeable upfield shift was detected. The H-1 NMR spectra of alkylpyrenium dications showed a much greater substituent dependency. Low temperature reactions of the less-reactive pyrene and 2,7-di-tert-butylpyrene with SbF5/SO2ClF led primaryl to sulfonylation sigma-complexes rather than oxidation dications. Persistent alkylpyrene radical cations were found to coexist with the alkylpyrenium ions of protonation in FSO3H/SO2 (ESR detection) without any noticeable line broadening in the NMR spectra of the Wheland intermediates.

  DOI：

  10.1021/jo00067a049
• 作为产物：
  描述：

  芘 、 溴代环己烷 、 三溴化铝 生成 1,3,6,8-tetracyclohexylpyrene
  参考文献：
  名称：

  BERG A.; LAM J.; HANSEN P. E., ACTA CHEM. SCAND., 40,(1986) N 8, 665-677

  摘要：

  DOI：