1,2,3-triphenylcyclopenta[a]indene | 106954-82-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,2,3-triphenylcyclopenta[a]indene
• 英文别名: 1,2,3-triphenylbenzopentalene；1,2,3-Triphenyl-benzopentalen；1,2,3-Triphenylcyclopenta(A)indene
• CAS: 106954-82-9
• 化学式: C₃₀H₂₀
• 分子量: 380.489
• InChiKey: FFICFPJEIOITOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  6.0
• 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

• 作为反应物：
  描述：

  1,2,3-triphenylcyclopenta[a]indene 在 溴 作用下， 生成 8,8a-Dibromo-1,2,3-triphenyl-8,8a-dihydro-cyclopenta[a]indene
  参考文献：
  名称：

  Pseudoaromatics: Synthesis of 1,2,3-Triphenylbenzopentalene and 1-(p-Methoxyphenyl)-2,3-Diphenylbenzopentalene

  摘要：

  DOI：

  10.1021/ja00867a046
• 作为产物：
  描述：

  3,3a-dihydroxy-1,2,3-triphenyl-2,3,3a,8a-tetrahydro-1H-cyclopent[a]inden-8-one 在 吡啶 、 lithium aluminium tetrahydride 、 三氯氧磷 作用下， 生成 1,2,3-triphenylcyclopenta[a]indene
  参考文献：
  名称：

  Pseudoaromatics: Synthesis of 1,2,3-Triphenylbenzopentalene and 1-(p-Methoxyphenyl)-2,3-Diphenylbenzopentalene

  摘要：

  DOI：

  10.1021/ja00867a046

文献信息

• Pentalenes with novel topologies: exploiting the cascade carbopalladation reaction between alkynes and gem-dibromoolefins
  作者：Gábor London、Margarete von Wantoch Rekowski、Oliver Dumele、W. Bernd Schweizer、Jean-Paul Gisselbrecht、Corinne Boudon、François Diederich

  DOI：10.1039/c3sc52623b

  日期：——

  A series of π-extended pentalenes with fused naphthyl-ring systems in different geometries were synthesised via a cascade carbopalladation reaction between alkynes and gem-dibromoolefins. This novel methodology was applied both in an intermolecular and an intramolecular fashion to access pentalenes with new topologies. The relationship between the fusion pattern and the opto-electronic properties within the synthesised series was investigated by UV/vis spectroscopy and electrochemical techniques. Novel pentalene reactivity, leading to yet unprecedented derivatives, was also uncovered.

  一系列具有融合萘环系统的π-扩展戊搭烯在不同几何结构中通过炔烃与对称二溴烯烃的级联碳钯化反应合成。这种新颖的方法学既在分子间也在分子内应用，以获得具有新拓扑结构的戊搭烯。通过紫外/可见光谱和电化学技术研究了合成系列中融合模式与光电子性质之间的关系。还揭示了导致前所未见的衍生物的新型戊搭烯反应性。
• The pyrolysis of tetraphenylphthalic anhydride: Formation of 1,2,3-triphenylbenzopentalene
  作者：Roger F.C. Brown、Karen S. Coulston、Frank W. Eastwood、Terry Korakis

  DOI：10.1016/s0040-4039(00)82456-9

  日期：——

  The primary product of flash vacuum pyrolysis of tetraphenylphthalic anhydride at 860°C/0.04 Torr is 1,2,3-triphenylbenzopentalene (74%) and not 1,2,3-triphenylbiphenylene, as suggested by Fields and Meyerson (1968) for the product of pyrolysis at 690°C with long contact time (15–20 sec.).

  正如Fields和Meyerson（1968）所建议的那样，在860°C / 0.04 Torr下，四苯基邻苯二甲酸酐的快速真空热解的主要产物是1,2,3-三苯基苯并戊烯（74％），而不是1,2,3-三苯基联亚苯。产物在690°C的高温下具有较长的接触时间（15–20秒）。
• An Exploration of Substituent Effects on the Photophysical Properties of Monobenzopentalenes
  作者：Tamás Gazdag、Enikő Meiszter、Péter J. Mayer、Tamás Holczbauer、Henrik Ottosson、Andrew B. Maurer、Maria Abrahamsson、Gábor London

  DOI：10.1002/cphc.202300737

  日期：2024.4.2

  A novel set of monobenzopentalenes have been synthesized and characterized that could provide an opportunity to advance molecular photonics and in particular the field of singlet fission.

  一组新型单苯并五烯的合成和表征可以为推进分子光子学，特别是单线态裂变领域提供机会。
• Cascade Carbopalladation Reaction between Alkynes and <i>gem</i>-Dibromoolefins: Facile Access to Monoannelated Pentalenes
  作者：Pablo Rivera-Fuentes、Margarete von Wantoch Rekowski、W. Bernd Schweizer、Jean-Paul Gisselbrecht、Corinne Boudon、François Diederich

  DOI：10.1021/ol301670d

  日期：2012.8.17

  A carbopalladation cascade reaction of easily accessible gem-dibromoolefins and alkynes furnishes monobenzo- and mononaphthopentalenes. The new chromophores accessed by this short route exhibit small HOMO-LUMO gaps and redox amphoteric behavior with tunable redox potentials.
• BROWN, ROGER F. C.;COULSTON, KAREN J.;EASTWOOD, FRANK W.;KORAKIS, TERRY, TETRAHEDRON LETT., 29,(1988) N 51, C. 6791-6792
  作者：BROWN, ROGER F. C.、COULSTON, KAREN J.、EASTWOOD, FRANK W.、KORAKIS, TERRY

  DOI：——

  日期：——