5,8-bis(1-chloroethenyl)-1,2-dihydrocyclopentafluoranthene | 148918-54-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,8-bis(1-chloroethenyl)-1,2-dihydrocyclopentafluoranthene
• 英文别名: 3,6-Bis(1-chloroethenyl)pentacyclo[9.5.2.02,7.08,17.014,18]octadeca-1(17),2,4,6,8,10,14(18),15-octaene
• CAS: 148918-54-1
• 化学式: C₂₂H₁₄Cl₂
• 分子量: 349.259
• InChiKey: JZRYRETVRHNUPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  5,8-bis(1-chloroethenyl)-1,2-dihydrocyclopentafluoranthene 在 苯亚硒酸酐 作用下， 以 氯苯 为溶剂， 反应 24.0h， 以86%的产率得到7,10-bis(1-chloroethenyl)-3,4-(dioxoethano)fluoranthene
  参考文献：
  名称：

  Improved Synthesis of a C₃₀H₁₂ Buckybowl via Benzylic Oxidation with Benzeneseleninic Anhydride

  摘要：

  DOI：

  10.1021/jo960627t
• 作为产物：
  描述：

  1,1'-(1,2-dihydrocyclopentafluoranthene-5,8-diyl)bisethanone 在 五氯化磷 作用下， 以 苯 为溶剂， 反应 3.0h， 以50%的产率得到5,8-bis(1-chloroethenyl)-1,2-dihydrocyclopentafluoranthene
  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

• "Locking" the bowl-shaped geometry of corannulene: cyclopentacorannulene
  作者：Atteye H. Abdourazak、Andrzej Sygula、Peter W. Rabideau

  DOI：10.1021/ja00060a073

  日期：1993.4

  The discovery that buckminsterfullerene, C[sub 60], is a stable molecule due to geodesic and electronic properties inherent in the truncated icosahedral cage structure has generated a renewed interest in hydrocarbons with curved surfaces. The carbon framework of corannulene, which can be considered to represent the polar cap of buckminsterfullerene, is surprisingly flexible. In spite of its substantial

  由于截头二十面体笼结构中固有的测地线和电子特性，巴克敏斯特富勒烯 C[sub 60] 是一种稳定的分子，这一发现重新引起了人们对具有弯曲表面的碳氢化合物的兴趣。可被认为代表巴克敏斯特富勒烯的极帽的可环烯的碳骨架非常灵活。尽管它有很大的曲率，但蒌烯在溶液中会经历快速的碗到碗反转，这就提出了一个问题，即蒌烯结构上需要多少个额外的稠环来锁定碗构象。在这里，我们提供的答案是碗变得刚性，至少在 NMR 时间尺度上，仅在稠合的五元环中添加两个碳。12 参考。
• Improved Synthesis of a C₃₀H₁₂ Buckybowl via Benzylic Oxidation with Benzeneseleninic Anhydride
  作者：Mark D. Clayton、Zbigniew Marcinow、Peter W. Rabideau

  DOI：10.1021/jo960627t

  日期：1996.1.1
• 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.