1,1'-(1,2-dihydrocyclopentafluoranthene-5,8-diyl)bisethanone | 148918-57-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,1'-(1,2-dihydrocyclopentafluoranthene-5,8-diyl)bisethanone
• 英文别名: 1-(6-acetyl-3-pentacyclo[9.5.2.02,7.08,17.014,18]octadeca-1(17),2,4,6,8,10,14(18),15-octaenyl)ethanone
• CAS: 148918-57-4
• 化学式: C₂₂H₁₆O₂
• 分子量: 312.368
• InChiKey: LADVSLRZYPUNEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1'-(1,2-dihydrocyclopentafluoranthene-5,8-diyl)bisethanone 在 N-溴代丁二酰亚胺(NBS) 、 五氯化磷 作用下， 以 苯 为溶剂， 反应 9.0h， 生成 1,2-Dibromo-5,8-bis-(1-chloro-vinyl)-1,2-dihydro-cyclopenta[cd]fluoranthene
  参考文献：
  名称：

  Cyclopentacorannulene:  π-Facial Stereoselective Deuterogenation and Determination of the Bowl-to-Bowl Inversion Barrier for a Constrained Buckybowl

  摘要：

  Attachment of an ethane or ethylene unit to the rim of corannulene produced relatively rigid bowls of dihydrocyclopenta- and cyclopentacorannulene, respectively. In contrast to the parent corannulenes, their inversion barriers are too high to be determined by the NMR coalescence methods. Due to the significant curvature of cyclopentacorannulene, deuterogenation is pi-facial specific; both heterogeneous and homogeneous catalysis lead exclusively to exo-dideuteriocyclopentacorannulene 2a. Equilibration of the endo- and exo-isotopomers allowed the determination of Delta G(double dagger) at 27.61-27.67 kcal/mol over the temperature range 52.1-99.3 degrees C and the estimation of Delta H-double dagger (27.3 +/- 0.7 kcal/mol) and Delta S-double dagger (-1.1 +/- 0.2 eu) for the bowl-to-bowl inversion. The inversion barrier calculated at the HF/6-31G*//3-21G level (25.9 kcal/mol) compares well with the experimental result.

  DOI：

  10.1021/ja9521987
• 作为产物：
  描述：

  2,5-降冰片二烯 、 5,7-diacetyl-1,2-dihydro-6H-dicyclopentacenaphthylen-6-one 以 正丁醇 为溶剂， 以64%的产率得到1,1'-(1,2-dihydrocyclopentafluoranthene-5,8-diyl)bisethanone
  参考文献：
  名称：

  Cyclopentacorannulene:  π-Facial Stereoselective Deuterogenation and Determination of the Bowl-to-Bowl Inversion Barrier for a Constrained Buckybowl

  摘要：

  Attachment of an ethane or ethylene unit to the rim of corannulene produced relatively rigid bowls of dihydrocyclopenta- and cyclopentacorannulene, respectively. In contrast to the parent corannulenes, their inversion barriers are too high to be determined by the NMR coalescence methods. Due to the significant curvature of cyclopentacorannulene, deuterogenation is pi-facial specific; both heterogeneous and homogeneous catalysis lead exclusively to exo-dideuteriocyclopentacorannulene 2a. Equilibration of the endo- and exo-isotopomers allowed the determination of Delta G(double dagger) at 27.61-27.67 kcal/mol over the temperature range 52.1-99.3 degrees C and the estimation of Delta H-double dagger (27.3 +/- 0.7 kcal/mol) and Delta S-double dagger (-1.1 +/- 0.2 eu) for the bowl-to-bowl inversion. The inversion barrier calculated at the HF/6-31G*//3-21G level (25.9 kcal/mol) compares well with the experimental result.

  DOI：

  10.1021/ja9521987

文献信息

• Cyclopentacorannulene:  π-Facial Stereoselective Deuterogenation and Determination of the Bowl-to-Bowl Inversion Barrier for a Constrained Buckybowl
  作者：Andrzej Sygula、Atteye H. Abdourazak、Peter W. Rabideau

  DOI：10.1021/ja9521987

  日期：1996.1.1

  Attachment of an ethane or ethylene unit to the rim of corannulene produced relatively rigid bowls of dihydrocyclopenta- and cyclopentacorannulene, respectively. In contrast to the parent corannulenes, their inversion barriers are too high to be determined by the NMR coalescence methods. Due to the significant curvature of cyclopentacorannulene, deuterogenation is pi-facial specific; both heterogeneous and homogeneous catalysis lead exclusively to exo-dideuteriocyclopentacorannulene 2a. Equilibration of the endo- and exo-isotopomers allowed the determination of Delta G(double dagger) at 27.61-27.67 kcal/mol over the temperature range 52.1-99.3 degrees C and the estimation of Delta H-double dagger (27.3 +/- 0.7 kcal/mol) and Delta S-double dagger (-1.1 +/- 0.2 eu) for the bowl-to-bowl inversion. The inversion barrier calculated at the HF/6-31G*//3-21G level (25.9 kcal/mol) compares well with the experimental result.