5,12-Bis-(4-dodecyloxy-phenyl)-6,13-diiodo-1,4,8,11-tetramethoxy-dibenzo[a,h]anthracene | 190371-89-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,12-Bis-(4-dodecyloxy-phenyl)-6,13-diiodo-1,4,8,11-tetramethoxy-dibenzo[a,h]anthracene
• 英文别名: 5,12-Bis(4-dodecoxyphenyl)-6,13-diiodo-1,4,8,11-tetramethoxynaphtho[1,2-b]phenanthrene
• CAS: 190371-89-2
• 化学式: C₆₂H₇₆I₂O₆
• 分子量: 1171.09
• InChiKey: SZMWYVRHDQOVSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.5
• 重原子数：
  70
• 可旋转键数：
  30
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,12-Bis-(4-dodecyloxy-phenyl)-6,13-diiodo-1,4,8,11-tetramethoxy-dibenzo[a,h]anthracene 在 仲丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以99%的产率得到5,12-Bis(4-dodecoxyphenyl)-1,4,8,11-tetramethoxynaphtho[1,2-b]phenanthrene
  参考文献：
  名称：

  Directed Electrophilic Cyclizations:  Efficient Methodology for the Synthesis of Fused Polycyclic Aromatics

  摘要：

  A versatile method for the synthesis of complex, fused polycyclic aromatic systems in high chemical yield is described. Construction is achieved using a general two-step synthetic sequence. Pd-catalyzed Suzuki and Negishi type cross-coupling chemistries allow for the preparation of nonfused skeletal ring systems in yields consistently > 80%. The critical ring-forming step, which generally proceeds in very high to quantitative yield, utilizes 4-alkoxyphenylethynyl groups and is induced by strong electrophiles such as trifluoroacetic acid and iodonium tetrafluoroborate. The reaction in essence produces phenanthrene moieties which are integrated into extended polycyclic aromatic structures. Fused polycyclic benzenoids as well as benzenoid/thiophene systems may be prepared utilizing this methodology. The scope of the described cross-coupling/cyclization chemistry including mechanistic insights and problematic side reactions are described.

  DOI：

  10.1021/ja9642673
• 作为产物：
  描述：

  1,4-Bis(2,5-dimethoxyphenyl)-2,5-bis[2-(4-dodecoxyphenyl)ethynyl]benzene 在 三氟甲磺酸 、 bis(pyridine)iodonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到5,12-Bis-(4-dodecyloxy-phenyl)-6,13-diiodo-1,4,8,11-tetramethoxy-dibenzo[a,h]anthracene
  参考文献：
  名称：

  通过亲电诱导环化反应制备稠合多环芳烃：在石墨带合成中的应用

  摘要：

  在过去几年中，共轭有机聚合物的研究和后续发展为研究人员提供了巨大的机会。这些材料的公认应用包括它们在发光二极管 (LED)、非线性光学 (NLO) 设备、轻型电池和传感设备中的使用。这些材料越来越多的用途和性能要求正在推动对更复杂结构的需求。经常限制许多结构复杂材料发展的一个因素是合成方法。在这份报告中，我们描述了一种结构复杂的材料，一种全碳共轭梯形聚合物或石墨带的合成。J 该合成的关键是开发了一种新型亲电试剂诱导的环化反应，该反应为稠合苯类芳烃系统 3 提供了一种强大的新途径，以高到定量的产率。我们选择追求全碳骨架，因为观察到显示最高电导率的共轭聚合物具有全碳骨架。据报道，特别是聚乙炔显示出与铜一样高的导电性 4 然而，由于其固有的不稳定性，聚乙炔的广泛开发尚未实现。具有更高二维结构度的全碳共轭体系，例如梯形聚合物，应该保持有趣的电子和光学特性，同时获得相对于聚乙炔的更高稳定性。我们的方法是合成单链

  DOI：

  10.1021/ja00096a056

文献信息

• Synthesis of Ethynyl-Substituted Quinquephenyls and Conversion to Extended Fused-Ring Structures
  作者：Marc B. Goldfinger、Khushrav B. Crawford、Timothy M. Swager

  DOI：10.1021/jo9721251

  日期：1998.3.1

  An organometallic coupling, electrophile-induced cyclization strategy for the synthesis of p-terphenyl compounds has been extended to the synthesis of p-quinquephenyl systems. In this work we report the synthesis of various polycyclic aromatic systems containing nine annelated rings including the synthesis of functionalized polycyclic aromatic systems. An interesting side reaction which leads to an indenyl spiro ring system is also described. This side reaction can be suppressed by changing the electrophile (from H+ to I+) or by modification of the cyclization precursor. The UV-vis and fluorescence spectra of several of these polycyclic aromatics and the p-quinquephenyl precursors are also reported.