(ortho-chlorophenyl)corannulene | 1165450-92-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (ortho-chlorophenyl)corannulene
• CAS: 1165450-92-9
• 化学式: C₂₆H₁₃Cl
• 分子量: 360.842
• InChiKey: BMLXOLODISIVBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.09
• 重原子数：
  27.0
• 可旋转键数：
  1.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (ortho-chlorophenyl)corannulene 在 双(三环己基膦)二氯化钯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 异丁酰胺 为溶剂， 反应 0.5h， 以100%的产率得到indeno[1,2,3-bc]corannulene
  参考文献：
  名称：

  Aromatic π-Systems More Curved Than C₆₀. The Complete Family of All Indenocorannulenes Synthesized by Iterative Microwave-Assisted Intramolecular Arylations

  摘要：

  Syntheses and X-ray crystal structures are reported for all seven members of the indenocorannulene family, comprising indenocorannulene, both isomers of diindenocorannulene, both isomers of triindenocorannulene, tetraindenocorannulene, and pentaindenocorannulene. With each additional indenoannulation, the pyramidalization of the trigonal carbon atoms at the hub of the corannulene increases. Five of the seven indenocorannulenes contain carbon atoms at the hub that are actually more pyramidalized than the carbon atoms of C-60. This work demonstrates, for the first time, that extended pi-systems with curvatures exceeding those of the most curved stable fullerenes and carbon nanotubes can be prepared by ordinary laboratory methods in solution, without recourse to high-temperature gas phase methods, such as flash vacuum pyrolysis. This proof of principle presages the days when scientists will be able to synthesize isomerically pure fullerenes and single-chirality nanotubes by well-understood, controlled chemical methods. Pentaindenocorannulene, itself, represents an attractive precursor to the C-5v end-cap of an all-carbon, single-walled, "armchair' [5,5]nanotube.

  DOI：

  10.1021/ja9031852
• 作为产物：
  描述：

  2-氯苯基硼酸 、 monobromocorannulene 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 36.0h， 以90%的产率得到(ortho-chlorophenyl)corannulene
  参考文献：
  名称：

  Aromatic π-Systems More Curved Than C₆₀. The Complete Family of All Indenocorannulenes Synthesized by Iterative Microwave-Assisted Intramolecular Arylations

  摘要：

  Syntheses and X-ray crystal structures are reported for all seven members of the indenocorannulene family, comprising indenocorannulene, both isomers of diindenocorannulene, both isomers of triindenocorannulene, tetraindenocorannulene, and pentaindenocorannulene. With each additional indenoannulation, the pyramidalization of the trigonal carbon atoms at the hub of the corannulene increases. Five of the seven indenocorannulenes contain carbon atoms at the hub that are actually more pyramidalized than the carbon atoms of C-60. This work demonstrates, for the first time, that extended pi-systems with curvatures exceeding those of the most curved stable fullerenes and carbon nanotubes can be prepared by ordinary laboratory methods in solution, without recourse to high-temperature gas phase methods, such as flash vacuum pyrolysis. This proof of principle presages the days when scientists will be able to synthesize isomerically pure fullerenes and single-chirality nanotubes by well-understood, controlled chemical methods. Pentaindenocorannulene, itself, represents an attractive precursor to the C-5v end-cap of an all-carbon, single-walled, "armchair' [5,5]nanotube.

  DOI：

  10.1021/ja9031852