triindeno[1,2,3-bc:1',2',3'-ef:1'',2'',3''-kl]corannulene | 1165450-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: triindeno[1,2,3-bc:1',2',3'-ef:1'',2'',3''-kl]corannulene
• 英文别名: Dodecacyclo[21.14.1.02,14.03,36.04,12.05,34.06,11.016,38.017,22.025,37.027,35.028,33]octatriaconta-1,3,5(34),6,8,10,12,14,16(38),17,19,21,23,25,27(35),28,30,32,36-nonadecaene；dodecacyclo[21.14.1.02,14.03,36.04,12.05,34.06,11.016,38.017,22.025,37.027,35.028,33]octatriaconta-1,3,5(34),6,8,10,12,14,16(38),17,19,21,23,25,27(35),28,30,32,36-nonadecaene
• CAS: 1165450-95-2
• 化学式: C₃₈H₁₆
• 分子量: 472.545
• InChiKey: QSLZUHYIBVRLSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  38
• 可旋转键数：
  0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  心环烯 、 2-氯苯基硼酸 在 一溴化碘 、 四(三苯基膦)钯 、 potassium carbonate 、 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 二氯甲烷 、 乙醇 、 水 、 甲苯 、 异丁酰胺 为溶剂， 反应 48.67h， 以7 mg的产率得到triindeno[1,2,3-bc:1',2',3'-ef:1'',2'',3''-kl]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

文献信息

• Aromatic π-Systems More Curved Than C₆₀. The Complete Family of All Indenocorannulenes Synthesized by Iterative Microwave-Assisted Intramolecular Arylations
  作者：Brian D. Steinberg、Edward A. Jackson、Alexander S. Filatov、Atsushi Wakamiya、Marina A. Petrukhina、Lawrence T. Scott

  DOI：10.1021/ja9031852

  日期：2009.8.5

  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.