2,6-bis-[2-(4-ethanoyloxyphenyl)ethenyl]pyridine | 94356-50-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2,6-bis-[2-(4-ethanoyloxyphenyl)ethenyl]pyridine
• 英文别名: 2,6-bis[2-(4-ethanoyloxyphenyl)ethenyl]pyridine；[4-[2-[6-[2-(4-Acetyloxyphenyl)ethenyl]pyridin-2-yl]ethenyl]phenyl] acetate
• CAS: 94356-50-0
• 化学式: C₂₅H₂₁NO₄
• 分子量: 399.446
• InChiKey: CFKKHQVDGPPNJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-bis-[2-(4-ethanoyloxyphenyl)ethenyl]pyridine 在 potassium hydroxide 、 二氧化碳 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以32%的产率得到2,6-bis[2-(4-hydroxyphenyl)ethenyl]pyridine
  参考文献：
  名称：

  弯曲形吡啶衍生物的超分子结构研究：从三环结晶化合物到五环介晶

  摘要：

  介绍了新弯曲核心介晶的介晶性质，并详细分析了相关三环化合物的分子堆积。

  DOI：

  10.1039/c6nj01515h
• 作为产物：
  描述：

  2,6-二甲基吡啶 、 乙酸酐 、 对羟基苯甲醛 反应 24.0h， 以60%的产率得到2,6-bis-[2-(4-ethanoyloxyphenyl)ethenyl]pyridine
  参考文献：
  名称：

  弯曲形吡啶衍生物的超分子结构研究：从三环结晶化合物到五环介晶

  摘要：

  介绍了新弯曲核心介晶的介晶性质，并详细分析了相关三环化合物的分子堆积。

  DOI：

  10.1039/c6nj01515h

文献信息

• Lobelane analogues containing 4-hydroxy and 4-(2-fluoroethoxy) aromatic substituents: Potent and selective inhibitors of [3H]dopamine uptake at the vesicular monoamine transporter-2
  作者：Shyamsunder R. Joolakanti、Justin R. Nickell、Venumadhav Janganati、Guangrong Zheng、Linda P. Dwoskin、Peter A. Crooks

  DOI：10.1016/j.bmcl.2016.03.119

  日期：2016.5

  (Ki = 30–70 nM). The two most potent analogues, 7 and 14, both exhibited a Ki value of 31 nM for inhibition of VMAT2. The lobelane analogue 14, incorporating 4-(2-fluoroethoxy) and 4-hydroxy aromatic substituents, exhibited 96- and 335-fold greater selectivity for VMAT2 versus DAT and SERT, respectively, in comparison to lobelane. Thus, lobelane analogues bearing hydroxyl and fluoroethoxy moieties retain

  合成了一系列含有芳香族 4-羟基和 4-(2-氟乙氧基) 取代基的山药烷和 GZ-793A 类似物，并评估了对囊泡单胺转运蛋白 2 (VMAT2) 的 [ 3 H]多巴胺 (DA) 摄取的抑制作用和多巴胺转运蛋白（DAT），以及血清素转运蛋白（SERT）的[ 3 H]血清素摄取。大多数这些化合物在纳摩尔范围内 ( K i = 30–70 nM) 表现出对 VMAT2 的 DA 摄取的有效抑制。两种最有效的类似物7和14均表现出抑制 VMAT2 的K i值为 31 nM。与洛贝烷相比，含有4-(2-氟乙氧基)和4-羟基芳族取代基的洛贝烷类似物14对VMAT2的选择性分别比DAT和SERT高96倍和335倍。因此，带有羟基和氟乙氧基部分的山药烷类似物保留了母体化合物对 VMAT2 的高亲和力，同时增强了对 VMAT2 相对于质膜转运蛋白的选择性。
• A structure–property relationship study of bent-core mesogens with pyridine as the central unit
  作者：J. M. Marković、N. P. Trišović、T. Tóth-Katona、M. K. Milčić、A. D. Marinković、C. Zhang、A. J. Jákli、K. Fodor-Csorba

  DOI：10.1039/c3nj01430d

  日期：——

  Three series of bent-core mesogens having pyridine as the central unit have been synthesized and characterized. A series of 2,6-diaminopyridine derivatives capable of forming inter- and intramolecular hydrogen bonds exhibit very high melting points. A decrease in the polarity of the central part of the bent-core obtained by replacing the amide with ester linkages results in derivatives with lower melting

  已经合成并表征了具有吡啶作为中心单元的三个系列的弯曲核液晶元。能够形成分子间和分子内氢键的一系列2,6-二氨基吡啶衍生物表现出非常高的熔点。通过用酯键取代酰胺而获得的弯曲核的中心部分的极性降低，导致衍生物具有较低的熔点并形成B2-和B7-样中间相。连接吡啶环和内部芳环的烯基的引入有助于进一步降低五环系统中央部分的极性，并导致B1和B7相的形成。通过光学显微镜观察和差示扫描量热法（DSC）确定了相，并通过X射线研究对其进行了确认。
• Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study
  作者：Jelena M. Marković、Nemanja P. Trišović、Dragosav Mutavdžić、Ksenija Radotić、Ivan O. Juranić、Branko J. Drakulić、Aleksandar D. Marinković

  DOI：10.1016/j.saa.2014.07.023

  日期：2015.1

  Seven symmetrical 2,6-distyrylpyridines, phenyl-substituted with hydrogen-bond donors, hydrogen-bond acceptors, halogens and hydrophobic moieties were synthesized and their spectroscopic characterization was done. Solvent effects on the absorption and fluorescence spectra were analyzed and quantified using the Kamlet-Taft and Catalan approach. The obtained results were rationalized by comparison of electrostatic potentials of the molecules in the ground and in excited state and by comparison of the frontier molecular orbitals (HOMO and LUMO), derived from quantum-mechanical calculations (HE, DFT, MP2). Analysis of the results revealed an important influence of non-specific (dispersive) interactions on the solvatochromic behavior of the compounds. 1D and 2D NMR data, in silica obtained conformational assembly of the compound, and the NMR analysis of molecular flexibility in solution (NAMFIS), were used to estimate population of conformers and to deconvolute the UV-Vis spectrum of representative derivative; inferring that the conformational assembly is more complex than was assumed in so far published literature data for this class of compounds. Along with this, the emission spectra of the representative compounds were decomposed by the Multivariate Curve Resolution analysis. (C) 2014 Elsevier B.V. All rights reserved.
• Investigation of supramolecular architectures of bent-shaped pyridine derivatives: from a three-ring crystalline compound towards five-ring mesogens
  作者：Nemanja Trišović、Jelena Antanasijević、Jelena Rogan、Dejan Poleti、Tibor Tóth-Katona、Miroslaw Salamonczyk、Antal Jákli、Katalin Fodor-Csorba

  DOI：10.1039/c6nj01515h

  日期：——

  The mesomorphic properties of new bent-core mesogens, coupled with the detailed analysis of the molecular packing of the related three-ring compounds is presented.

  介绍了新弯曲核心介晶的介晶性质，并详细分析了相关三环化合物的分子堆积。