3,9-dimethoxyperylene | 1041185-12-9

• 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: 3,9-dimethoxyperylene
• 英文别名: 3,9-Dimethoxyperylene
• CAS: 1041185-12-9
• 化学式: C₂₂H₁₆O₂
• 分子量: 312.368
• InChiKey: PNIPHPVYAKPRRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-甲氧基-1,2,3,4-四氢-1-萘酚 在 palladium on activated charcoal 对甲苯磺酸 作用下， 以 环丁砜 、 均三甲苯 为溶剂， 反应 2.0h， 以75%的产率得到3,9-dimethoxyperylene
  参考文献：
  名称：

  Tandem Friedel−Crafts Annulation to Novel Perylene Analogues

  摘要：

  [GRAPHICS]Novel dialkyloxy- and dihydroxyoctahydroperylenes are regioselectively available via a new tandem Friedel-Crafts alkylation of tetrahydronaphthalene precursors followed by oxidative aromatization. Heating of 5-alkyloxy-1-tetralol with p-toluenesulfonic acid in sulfolane gave the corresponding octahydroperylenes in moderate yields. Studies with Lewis acids and tetralin-1,5-diol in acetonitrile at room temperature provided the 4,10-dihydroxy analogue cleanly, albeit in reduced yields. Examples of these new series of perylene analogues were partially oxidized to the corresponding contiguously aromatic, anthracene core products or fully aromatized to 3,9-dialkyloxyperylenes in good yields.

  DOI：

  10.1021/jo800558c

文献信息

• The photophysical characterisation of novel 3,9-dialkyloxy- and diacyloxyperylenes
  作者：John F. Fuini、Anand B. Surampudi、Mark A. Penick、Mathew P.D. Mahindaratne、George R. Negrete、Lorenzo Brancaleon

  DOI：10.1016/j.dyepig.2010.06.009

  日期：2011.2

  The fundamental photophysical properties of three symmetrically substituted 3,9-perylene analogues were examined in a diverse range of solvents. All three compounds exhibited solvent-dependent fluorescence quantum yield, which was lower than that of perylene or its diimides. Whilst the absence of a large excited state dipole moment suggests that there is no preferential charge accumulation in one side of the molecules, the data suggest that intramolecular electron transfer occurs and that such an event causes additional photochemical mechanisms in chlorinated compounds where the fluorescence quantum yield is lower than in all other solvents and the values of the fluorescence decay change significantly. The dyes could be an interesting new class of fluorescence tags for labeling biomolecules and as dyes for organic photovoltaic materials. (C) 2010 Elsevier Ltd. All rights reserved.
• Tandem Friedel−Crafts Annulation to Novel Perylene Analogues
  作者：Mark A. Penick、Mathew P. D. Mahindaratne、Robert D. Gutierrez、Terrill D. Smith、Edward R. T. Tiekink、George R. Negrete

  DOI：10.1021/jo800558c

  日期：2008.8.1

  [GRAPHICS]Novel dialkyloxy- and dihydroxyoctahydroperylenes are regioselectively available via a new tandem Friedel-Crafts alkylation of tetrahydronaphthalene precursors followed by oxidative aromatization. Heating of 5-alkyloxy-1-tetralol with p-toluenesulfonic acid in sulfolane gave the corresponding octahydroperylenes in moderate yields. Studies with Lewis acids and tetralin-1,5-diol in acetonitrile at room temperature provided the 4,10-dihydroxy analogue cleanly, albeit in reduced yields. Examples of these new series of perylene analogues were partially oxidized to the corresponding contiguously aromatic, anthracene core products or fully aromatized to 3,9-dialkyloxyperylenes in good yields.