6,11,20,25,34,39-Hexa(propan-2-yl)tridecacyclo[28.12.0.02,15.03,8.04,41.09,14.013,18.016,29.017,22.023,28.027,32.031,36.037,42]dotetraconta-1,3,5,7,9,11,13,15,17(22),18,20,23,25,27(32),28,30,33,35,37(42),38,40-henicosaene | 271255-89-1

• 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: 6,11,20,25,34,39-Hexa(propan-2-yl)tridecacyclo[28.12.0.02,15.03,8.04,41.09,14.013,18.016,29.017,22.023,28.027,32.031,36.037,42]dotetraconta-1,3,5,7,9,11,13,15,17(22),18,20,23,25,27(32),28,30,33,35,37(42),38,40-henicosaene
• CAS: 271255-89-1
• 化学式: C₆₀H₅₄
• 分子量: 775.089
• InChiKey: QMRAZUYGUJHHSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.8
• 重原子数：
  60
• 可旋转键数：
  6
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  6,11,20,25,34,39-Hexa(propan-2-yl)tridecacyclo[28.12.0.02,15.03,8.04,41.09,14.013,18.016,29.017,22.023,28.027,32.031,36.037,42]dotetraconta-1,3,5,7,9,11,13,15,17(22),18,20,23,25,27(32),28,30,33,35,37(42),38,40-henicosaene 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 65.0 ℃ 、6.0 MPa 条件下， 反应 12.0h， 以40%的产率得到6,11,20,25,34,39-Hexa(propan-2-yl)tridecacyclo[28.12.0.02,15.03,8.04,41.09,14.013,18.016,29.017,22.023,28.027,32.031,36.037,42]dotetraconta-1(42),2,4(41),8,13(18),14,16,22,27(32),28,30,36-dodecaene
  参考文献：
  名称：

  Peralkylated Coronenes via Regiospecific Hydrogenation of Hexa-peri-hexabenzocoronenes

  摘要：

  A remarkable, regiospecific hydrogenation zips around the similar to4 nm perimeter of hexa-peri-hexabenzocoronenes (HBC) adding 18 hydrogen atoms, leading to the first peralkylated coronenes, in quantitative yields in some cases. Increasing steric bulk of side chains was found to hinder the reaction, while unsubstituted HBC could be converted to a modest extent despite its vanishing solubility. The structures of the novel coronenes are unequivocally confirmed by MALDI-TOF, H-1, C-13, and heteronuclear correlation NMR, and UV-vis absorption spectroscopy. The puckered-ring periphery of these discotics does not prohibit self-assembly to columnar structures in a fashion similar to that of the planar precursors, as determined from wide-angle X-ray diffraction, but decreases the isotropization temperature by similar to300 degreesC relative to the latter. Branching in the alkyl chains frustrates nucleation from the melt, resulting in clear polymorphism depending on the thermal treatment. Nonetheless, preliminary measurements indicate high charge-carrier mobilities and lifetimes within the bulk material, on the same order as those previously found for HBCs.

  DOI：

  10.1021/ja037522+
• 作为产物：
  描述：

  1,2,3,4,5,6-Hexakis(4-propan-2-ylphenyl)benzene 在 甲烷磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以99%的产率得到6,11,20,25,34,39-Hexa(propan-2-yl)tridecacyclo[28.12.0.02,15.03,8.04,41.09,14.013,18.016,29.017,22.023,28.027,32.031,36.037,42]dotetraconta-1,3,5,7,9,11,13,15,17(22),18,20,23,25,27(32),28,30,33,35,37(42),38,40-henicosaene
  参考文献：
  名称：

  Oxidative C−C Bond Formation (Scholl Reaction) with DDQ as an Efficient and Easily Recyclable Oxidant

  摘要：

  DDQ in the presence of an acid is known to oxidize a variety of aromatic donors to the corresponding cation radicals. Herein, we now demonstrate that the DDQ/H+ system can be effectively utilized for the oxidative C-C bond formations or biaryl synthesis. The efficient preparation of a variety of polyaromatic hydrocarbons including graphitic hexa-peri-hexabenzocoronenes, ease of isolation of the clean products, and ready regeneration of DDQ from easily recovered reduced DDQ-H-2 advances the use of DDQ/H+ for Scholl reactions.

  DOI：

  10.1021/ol901331p

文献信息

• Synthesis and electronic properties of iso-alkyl substituted hexa-peri-hexabenzocoronenes (HBC’s) from a versatile new HBC synthon, hexakis(4-acetylphenyl)benzene
  作者：Vincent J. Chebny、Chengeto Gwengo、James R. Gardinier、Rajendra Rathore

  DOI：10.1016/j.tetlet.2008.06.005

  日期：2008.8

  Simple syntheses of a variety of soluble hexa-peri-hexabenzocoronenes are accomplished using an easily prepared hexakis(4-acetylphenyl)benzene as a common precursor. The concentration-dependent emissions of various HBCs in solution indicate that they undergo extensive aggregation despite the presence of bulky (peripheral) isoalkyl and tert-butyl groups. The various planar HBC's undergo reversible electrochemical oxidations and form stable monomeric cation-radical salts in solution. (C) 2008 Elsevier Ltd. All rights reserved.