2,6-dimethyl-4-(4,6,8-trimethyl-azulen-1-yl)-pyridine

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 2,6-dimethyl-4-(4,6,8-trimethyl-azulen-1-yl)-pyridine
• 英文别名: 2,6-Dimethyl-4-(4,6,8-trimethylazulen-1-yl)pyridine
• 化学式: C₂₀H₂₁N
• 分子量: 275.393
• InChiKey: UKMDIKABIGHRBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-4-(4,6,8-trimethyl-azulen-1-yl)-pyridine 、 偶氮苯六氟磷酸盐 以 aq. acetate buffer 为溶剂， 生成 (E)-[3-(2,6-dimethylpyridin-4-yl)-4,6,8-trimethylazulen-1-yl]phenyldiazene
  参考文献：
  名称：

  Photochemistry of Fluorescent Azobenzenes Substituted with Azulenylpyridine Moiety

  摘要：

  Fluorescent properties and the photoisomerization behaviour of 4-azulenylpyridine-substituted azobenzenes were investigated. All studied compounds have shown fluorescent emission in solution, originating from excited singlet state S-2 -> S-0 of azulene moiety. The substitution of the azobenzene chromophore has affected the preservation of the fluorescence emission in thin films prepared in PMMA matrix. Correlation of absorption spectra with H-1-NMR spectroscopy revealed that for all compounds the E -> Z isomerization takes place upon exposure to UV light.

  DOI：

  10.1080/15421406.2014.967653
• 作为产物：
  描述：

  2,6-二甲基-4-吡喃酮 在 高氯酸 、 ammonium acetate 、 三氯氧磷 作用下， 以 硝基甲烷 、 乙醇 为溶剂， 生成 2,6-dimethyl-4-(4,6,8-trimethyl-azulen-1-yl)-pyridine
  参考文献：
  名称：

  在2和6位上被2-（2-呋喃基）乙烯基，2-（2-噻吩基）乙烯基或2-（3-噻吩基）乙烯基部分取代的4-（Azulen-1-基）六元杂芳族化合物

  摘要：

  合成了吡啶鎓和吡啶鎓盐和吡啶，吡啶在第4位具有氮杂-1-基部分，在位置2和6具有两个2-杂芳基乙烯基。从吡喃酮开始获得吡啶盐，并且可以通过用乙酸铵处理由这些盐制备吡啶。当将吡啶鎓盐用于上面获得的吡啶鎓盐时，不会发生合成吡啶鎓盐的一般程序，该程序在较少离域的电子系统中会产生良好的结果。因此，使用4-（azulen-1-yl）-1-（n-丁基）-2,6-二甲基吡啶高氯酸盐作为起始原料，将其与杂芳基甲醛缩合。这些化合物已被完全表征，并讨论了一些光谱。揭示了它们与某些金属离子的相互作用，观察亲和力比简单的azulenepyridines更好。在本文的最后部分，提供了几种吡啶盐和吡啶的氧化还原电势，与未乙烯基化衍生物的氧化还原电势相比。

  DOI：

  10.1016/j.tet.2017.03.035

文献信息

• Azulene-substituted pyridines and pyridinium salts. Synthesis and structure. 1. Azulene-substituted pyridines
  作者：Alexandru C. Razus、Liviu Birzan、Claudia Pavel、Oana Lehadus、Andreea Corbu、Filip Chiraleu、Cristian Enache

  DOI：10.1002/jhet.5570440142

  日期：2007.1

  4-Azulen-1-yl substituted 2,6-dimethyl-and 2,6-diphenyl-pyridines are obtained in good yields from the reaction of corresponding 4-azulen-1-yl-pyranylium salts and ammonium acetate in ethanol or starting from 4-chloro-2,6-diphenyl-pyranylium salts in two steps: reaction with azulenes followed by in situ treatment with ammonium acetate. The effect of substitution at the 3-position of the heterocycle

  从相应的4-氮杂-1-基-吡喃鎓盐与乙酸铵在乙醇中的反应或从4-氯-2,6-二苯基-吡喃鎓盐分两个步骤：与天青石反应，然后用乙酸铵原位处理。考虑了在杂环的3-位的取代作用。用NMR和uv-vis光谱完成结构分配。
• Synthesis and physico-chemical properties of highly conjugated azo-aromatic systems. 4-(azulen-1-yl)-pyridines with mono- and bis azo-aromatic moieties at C3-position of azulene
  作者：Alexandru C. Razus、Simona Nica、Liliana Cristian、Matei Raicopol、Liviu Birzan、Andreea Eugenia Dragu

  DOI：10.1016/j.dyepig.2011.02.008

  日期：2011.10

  Highly conjugated azo-aromatic systems have been prepared in high to moderate yields by linking mono- and bis-azo aromatic fragments to 4-(Rn-azulen-1-yl)-2,6-dimethyl-pyridine. The synthesized pi-extended systems have been studied by NMR spectroscopy, UV-Vis and electrochemistry. Systematic increase of the conjugation along the azobenzene skeleton has affected the spectral properties of the azophenyl substituted 4-(azulen-1-yl)-pyridine. The synthesized compounds exhibit a bathochromic shift of the visible absorption maxima with the increase of the conjugating skeleton and introduction of an electron-withdrawing group. The electrochemical behavior revealed a high stability toward oxidation owing to the higher polarization induced by the azulenylpyridine moiety. (C) 2011 Elsevier Ltd. All rights reserved.
• 4-(Azulen-1-yl) six-membered heteroaromatics substituted in 2- and 6- positions with 2-(2-furyl)vinyl, 2-(2-thienyl)vinyl or 2-(3-thienyl)vinyl moieties
  作者：Liviu Birzan、Mihaela Cristea、Constantin C. Draghici、Victorita Tecuceanu、Anamaria Hanganu、Eleonora-Mihaela Ungureanu、Alexandru C. Razus

  DOI：10.1016/j.tet.2017.03.035

  日期：2017.4

  of pyridinium salts, which occur with good results in less delocalized electronic systems, do not take place when applied to the above obtained pyrylium salts. Therefore, as starting material 4-(azulen-1-yl)-1-(n-butyl)-2,6-dimethylpyridinium perchlorate was used, which was condensed with heteroarylcarboxaldehydes. These compounds were completely characterized and some of their spectra were discussed

  合成了吡啶鎓和吡啶鎓盐和吡啶，吡啶在第4位具有氮杂-1-基部分，在位置2和6具有两个2-杂芳基乙烯基。从吡喃酮开始获得吡啶盐，并且可以通过用乙酸铵处理由这些盐制备吡啶。当将吡啶鎓盐用于上面获得的吡啶鎓盐时，不会发生合成吡啶鎓盐的一般程序，该程序在较少离域的电子系统中会产生良好的结果。因此，使用4-（azulen-1-yl）-1-（n-丁基）-2,6-二甲基吡啶高氯酸盐作为起始原料，将其与杂芳基甲醛缩合。这些化合物已被完全表征，并讨论了一些光谱。揭示了它们与某些金属离子的相互作用，观察亲和力比简单的azulenepyridines更好。在本文的最后部分，提供了几种吡啶盐和吡啶的氧化还原电势，与未乙烯基化衍生物的氧化还原电势相比。
• Photochemistry of Fluorescent Azobenzenes Substituted with Azulenylpyridine Moiety
  作者：Eugenia Andreea Dragu、Anamaria Hanganu、Ileana Rau、Francois Kajzar、Alexandrina Tane、Alexandru C. Razus、Simona Nica

  DOI：10.1080/15421406.2014.967653

  日期：2014.11.22

  Fluorescent properties and the photoisomerization behaviour of 4-azulenylpyridine-substituted azobenzenes were investigated. All studied compounds have shown fluorescent emission in solution, originating from excited singlet state S-2 -> S-0 of azulene moiety. The substitution of the azobenzene chromophore has affected the preservation of the fluorescence emission in thin films prepared in PMMA matrix. Correlation of absorption spectra with H-1-NMR spectroscopy revealed that for all compounds the E -> Z isomerization takes place upon exposure to UV light.