2,7-di-tert-pentylpyrene | 78751-82-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 2,7-di-tert-pentylpyrene
• 英文别名: 2,7-di-tert-amylpyrene；2,7-Bis(1,1-dimethylpropyl)pyrene；2,7-bis(2-methylbutan-2-yl)pyrene
• CAS: 78751-82-3
• 化学式: C₂₆H₃₀
• 分子量: 342.524
• InChiKey: ASFNDOKQEJOAKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  473.0±15.0 °C(Predicted)
• 密度：
  1.043±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  2,7-di-tert-pentylpyrene 在 氯氟磺酰 、 五氟化锑 作用下， 以 various solvent(s) 为溶剂， 生成 2,7-di-tert-amylpyrene 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