1,3,6,8-tetracyclopentylpyrene | 78751-90-3

• 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-tetracyclopentylpyrene
• CAS: 78751-90-3
• 化学式: C₃₆H₄₂
• 分子量: 474.729
• InChiKey: ZBEYNRYEIDUKQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.56
• 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-tetracyclopentylpyrene 在 N-fluoro-2,4-dinitroimidazole 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 72.0h， 以13%的产率得到1,3,6,8-Tetracyclopentyl-4-fluoro-pyrene
  参考文献：
  名称：

  Facile one-pot fluorination of polycyclic aromatic hydrocarbons (PAHs) with N-fluoro-2,4-dinitroimidazole; scope and limitation

  摘要：

  The synthetic utility of N-fluoro-2,4-dinitro-imidazole 'NF-2,4-DNI', a recently introduced NF fluorinating agent, has been tested for direct one-pot fluorination of several classes of polycyclic aromatic hydrocarbons, PAHs, namely pyrene, crowded alkyl(cycloalkyl)-pyrenes; hexahydro- and tetrahydro-pyrene; benzo[a] anthracene; benzo[a]- and benzo[e]pyrene; perylene; 2,7-di-tert-butylphenanthrene; chrysene; 9-methylanthracene and anthracene, as well as trans-15, 16-dimethyl-dihydropyrene; azuleno[1,2-a] acenaphthylene and azulene. Although the isolated yields are modest, the ease of handling of the reagent, simple operation (reflux in dichloroethane for 3 days) and the use of 1.1 equivalent of the reagent makes the procedure quite attractive for polynuclear aromatics, avoiding multi-step operations (NO2-PAH-->NH2-PAH-->N-2(+)-PAH-->F-PAH) or the use of toxic or costly reagents (CF3OF, XeF2, etc.); it provides direct one-pot access to a variety of F-PAHs that are not readily made using other fluorinating agents. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(98)00224-3
• 作为产物：
  描述：

  芘 、 溴代环戊烷 、 三溴化铝 生成 1,3,6,8-tetracyclopentylpyrene
  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：

文献信息

• Oxidation of sterically crowded alkyl(cycloalkyl)pyrenes. Persistent dications in SbF5/SO2ClF and radical cations in FSO3H/SO2
  作者：Kenneth K. Laali、Poul Erik Hansen、Edward Gelerinter、John J. Houser

  DOI：10.1021/jo00067a049

  日期：1993.7

  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.