4-(1-naphthylvinyl)pyridine | 16375-78-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(1-naphthylvinyl)pyridine
• 英文别名: 4-nvp；trans-1-(1-naphthyl)-2-(4-pyridyl)-ethylene；(E)-4-(2-(naphthalen-1-yl)vinyl)pyridine；(E)-4-(2-(1-naphthyl)vinyl)pyridine；4-[(E)-2-naphthalen-1-ylethenyl]pyridine
• CAS: 16375-78-3
• 化学式: C₁₇H₁₃N
• 分子量: 231.297
• InChiKey: FLKDRTOVVLNOLV-CMDGGOBGSA-N

物化性质

• 熔点：
  167-169 °C
• 沸点：
  409.3±20.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4-(1-naphthylvinyl)pyridine 在 乙醇 作用下， 以 1,4-二氧六环 为溶剂， 生成 1-(3-Hydroxy-2-oxo-propyl)-4-((E)-2-naphthalen-1-yl-vinyl)-pyridinium; bromide
  参考文献：
  名称：

  Evaluation of the side arm of (naphthylvinyl)pyridinium inhibitors of choline acetyltransferase

  摘要：

  A number of quaternary salts of trans-4-(beta-1-naphthylvinyl)pyridine (NVP) were synthesized and evaluated as inhibitors of the enzymes choline acetyltransferase (ChAT) and acetylcholinesterase (AChE). Structural variations in the side arm attached to the pyridine nitrogen atom demonstrate that an inductive effect is small but significant for activity. Inhibition of ChAT by alkylated derivatives decreases when electron-withdrawing groups are placed in the side chain. Substitution of a methyl group on the pyridine ring only slightly affects activities toward ChAT and AChE. When the pyridinium moiety is replaced by an imidazolium ring, no ChAT inhibition was observed. The imidazolium compound, however, was a weak inhibitor of AChE. For design of affinity columns for purification of ChAT, the data also supports the use of long chain alkylated amide derivatives of NVP.

  DOI：

  10.1021/jm00396a017
• 作为产物：
  描述：

  1-(1-naphthyl)-2-pyridin-4-ylethanol 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以83%的产率得到4-(1-naphthylvinyl)pyridine
  参考文献：
  名称：

  多环氮杂芳烃的光化学环化脱氢路线

  摘要：

  本文报道了光化学环化脱氢制备多环氮杂芳烃的研究。从 2-、3- 和 4-[2-(1- 和 2-萘基)乙烯基]吡啶获得各种萘喹啉和萘异喹啉。4-[2-(3-菲基)乙烯基]吡啶得到芘[1,10-HIJ]异喹啉。描述了 (2-芳基乙烯基) 吡啶的有效制备方法。

  DOI：

  10.1055/s-2007-983745

文献信息

• Molecular size and flexibility as determinants of selectivity in the oxidation of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analogs by monoamine oxidase A and B
  作者：S. M. N. Efange、R. H. Michelson、A. K. Tan、M. J. Krueger、T. P. Singer

  DOI：10.1021/jm00061a020

  日期：1993.4

  In the present study, a number of isomeric 4-naphthyl-, 4-(naphthylalkyl)-, 4-thienyl-, and 4-(thienylalkyl)tetrahydropyridines, conformationally restrained and flexible analogs of MPTP, were synthesized and evaluated as potential selective substrates of MAO A and B. In terms of the parameter (turnover number)/Km, the bulky naphthyl analogs were invariably better substrates of MAO A than kynuramine

  在1-甲基-4-苯基-1,2,3,6-四氢吡啶（MPTP）的苯基和四氢吡啶基部分之间引入亚甲基桥导致单胺氧化酶B（MAO B）的选择性比单胺氧化酶A（毛A）。然而，该桥的延长导致选择性的完全丧失。在本研究中，合成了多种异构的4-TPP的构象受限和灵活的类似物4-萘基-，4-（萘基烷基）-，4-噻吩基-和4-（噻吩基烷基）四氢吡啶，并将其评估为潜在的选择性底物就参数（周转数）/ Km而言，笨重的萘基类似物总是比该酶的参考底物Kynuramine更好的MAO A底物。此外，所有萘类似物，无论构象迁移率如何，同样，发现所有噻吩基类似物都是MAO B的更有效底物。与萘相反，构象受约束的噻吩9a和10a被认为是MAO B的较差底物，相对于苄胺，参考底物。这些结果表明，这些化合物对MAO A或B的选择性取决于分子大小和柔韧性的复杂相互作用。在这种相互作用中，这两个因素之一可能占主导地位。这些结果表明，这些化合物对MAO
• [2 + 2] Photodimerization of Naphthylvinylpyridines through Cation-π Interactions in Acidic Solution
  作者：Shinji Yamada、Yuka Nojiri

  DOI：10.3390/molecules22030491

  日期：——

  high-pressure mercury lamp in acidic solution afforded synHT dimers in high stereoselectivities. Similar results were obtained by visible light irradiation. On the other hand, when the reactions were carried out under neutral conditions, the stereoselectivities were very low, and the yields were decreased by visible light irradiation. Comparison of the UV-vis spectra between the acidic and the neutral conditions

  用250 W高压照射（E）-4-（2-（2-萘基）乙烯基）吡啶（1a）和（E）-4-（2-（1-萘基乙烯基）吡啶）（1b）酸性溶液中的汞灯可提供高立体选择性的synHT二聚体。通过可见光照射获得类似的结果。另一方面，当反应在中性条件下进行时，立体选择性非常低，并且通过可见光照射降低了产率。酸性和中性条件之间的紫外可见光谱比较表明，在酸性溶液中观察到红移。这些结果表明，HCl不仅在通过阳离子-π相互作用对底物进行预取向中，而且在使能可见光反应的底物的吸收性质变化中都起着重要作用。
• Observance of a large conformational change associated with the rotation of the naphthyl groups during the photodimerization of criss-cross aligned CC bonds within a 2D coordination polymer
  作者：Fei-Long Hu、Shu-Long Wang、Brendan F. Abrahams、Jian-Ping Lang

  DOI：10.1039/c5ce00594a

  日期：——

  (4-npy)0.25 (3a) (H2oba = 4,4′-oxydibenzoic acid; 4-spy = (E)-4-styrylpyridine; HT-ppcb = 1,3-bis(4-pyridyl)-2,4-bis(phenyl)cyclobutane; 4-(2-npy) = (E)-4-(2-(naphthalen-2-yl)vinyl)pyridine; 4-npy = (E)-4-(2-(naphthalen-1-yl)vinyl)pyridine; HT-pncb = rctt-1,3-bis(4-pyridyl)-2,4-bis(1-naphthyl)cyclobutane) were structurally determined. In each case, pairs of Zn(II) centres are linked by oba2− anions to form

  五种配位聚合物[Zn（oba）（4-spy）] 2 ·（4-spy）0.25 ·（H 2 O）（1），[Zn 2（oba）2（HT-ppcb）] 2 ·（4- spy）0.25（1a），[Zn（oba）（4-（2-npy））] 2 ·（4-（2-npy））0.25 ·（H 2 O）1.25（2），[Zn（oba） （4-npy）] 2 ·（4-npy）0.25（3）和[Zn2（oba）2（HT-pncb）]·（4-npy）0.25（3a）（H 2 oba = 4,4 '-氧二苯甲酸; 4-间谍=（E）-4-苯乙烯基吡啶; HT-ppcb = 1,3-双（4-吡啶基）-2,4-双（苯基）环丁烷; 4-（2-npy）=（E）-4-（2-（萘-2-基）乙烯基）吡啶; 4-npy =（E）-4-（2-（萘-1-基）乙烯基）吡啶; 在结构上确定HT-pncb ＝rctt -1，3-双（4-吡啶基）-
• Effect of the nitrogen heteroatom on the photophysics and photochemistry of <i>trans</i> -1-styrylnaphthalene and <i>trans</i> -9-styrylphenanthrene in different solvents
  作者：Giampiero Bartocci、Ugo Mazzucato、Anna Spalletti

  DOI：10.1002/recl.19951141106

  日期：——

  The effect of the nitrogen heteroatom on the excited state properties of trans-1-styryl-naphthalene (1-StN) and trans-9-styrylphenanthrene (9-StPh) has been investigated by fluorimetric and photochemical techniques. The relaxation processes of two aza analogues of each of these diarylethylenes, bearing the nitrogen atom in the mono- and polycyclic aryl group, respectively, were studied in different

  通过荧光和光化学技术研究了氮杂原子对反式-1-苯乙烯基萘（1-StN）和反式-9-苯乙烯基菲（9-StPh）的激发态性质的影响。在不同的溶剂中和在较大的温度范围内，研究了每种二芳基乙烯的两个氮杂类似物的弛豫过程，这些氮杂类似物分别在单环和多环芳基中带有氮原子。与母体烃相比，氮杂衍生物具有较小的辐射和较大的反应衰变产率。所述极性溶剂降低了扭转能量势垒并有利于反式 顺式光异构化而分子内氢键可以在反应性失活的速率减慢。
• Supramolecular Aggregate of Cadmium(II)-Based One-Dimensional Coordination Polymer for Device Fabrication and Sensor Application
  作者：Basudeb Dutta、Rajkumar Jana、Anup Kumar Bhanja、Partha Pratim Ray、Chittaranjan Sinha、Mohammad Hedayetullah Mir

  DOI：10.1021/acs.inorgchem.8b03294

  日期：2019.2.18

  Interestingly, compound 1 shows increasing conductivity upon irradiation of light. Therefore, it has the potential to be used in optoelectronic devices. Moreover, the supramolecular assembly of 1 specifically detects Cr3+ cation in the presence of other competitive analytes. Most importantly, compound 1 exhibits fascinating turn-on Cr3+ sensing, which seems to be an ornament in the field of sensing application

  新型混合配体一维配位聚合物（1D CP）[Cd 2（adc）2（4-nvp）6 ]·（MeOH）·（H 2 O）} n（1 ; H 2 adc = 9已经合成了10-蒽二羧酸和4-nvp ＝ 4-（1-萘基乙烯基）吡啶），并通过单晶X射线晶体学对其结构进行了表征。一维聚合物通过氢键，CH–··π和π···π相互作用进行超分子聚集。有趣的是，化合物1在光照射下显示出增加的电导率。因此，它具有在光电设备中使用的潜力。另外，超分子组装体1特异性地检测Cr。其他竞争性分析物存在下的3+阳离子。最重要的是，化合物1表现出令人着迷的Cr 3+开启感应，这似乎是感应应用领域的装饰品。