(E)-1-(4-ethynylphenyl)-2-(4-pyridyl)ethylene | 189190-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-(4-ethynylphenyl)-2-(4-pyridyl)ethylene
• 英文别名: 4-[(E)-2-(4-ethynylphenyl)ethenyl]pyridine
• CAS: 189190-26-9
• 化学式: C₁₅H₁₁N
• 分子量: 205.259
• InChiKey: OFUQQTUMCYXMPW-BQYQJAHWSA-N

物化性质

• 熔点：
  187-190 °C
• 沸点：
  348.5±21.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• 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：

  (E)-1-(4-ethynylphenyl)-2-(4-pyridyl)ethylene 在 吡啶 、 copper(I) chloride 、 氧气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  π-Extended conjugate phenylacetylenes. Synthesis of 4-[(E) and (Z)-2-(4-ethenylphenyl)ethenyl]pyridine. Dimerization, quaternation and formation of charge–transfer complexes

  摘要：

  The conjugate (E)- and (Z)-(4'-pyridylethenyl)-4-phenylethyne (E-4 and Z-4) has been satisfactorily prepared by two different routes: (a) by dehydrohalogenation of 4'-pyridylethenyl-4-phenyi-beta-chloroethene; (b) by the Wittig reaction between p-(iodobenzyl)(triphenyl)phosphine ylide and 4-pyridinecarboxaldehyde, E/Z isomer separation, and cross-coupling with 2-methyl-but-3-yn-2-ol followed the propanone elimination. The Glaser oxidative dimerization of (Z)-4 yields (Z,Z)-1,4-di[(4'-pyridylethenyl)-4-phenyll-buta-1,3-diyne in good yield, (Z,Z)-5. (E,E)-5 was obtained by phase transfer oxidative dimerisation of (E)-4 in presence of their N-methyl salt (E)-10. Mono-and di-N-methylated salts of conjugate (E,E)-5 and (Z,Z)-5, were obtained by quaternation with iodomethane. The (Z,Z)-5 di-N-methylated salt forms charge-transfer complexes with TCNE, TCNQ and TMPD. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01628-9
• 作为产物：
  描述：

  4-碘苄基溴 在 copper(I) chloride 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 potassium tert-butylate 、 二乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 74.5h， 生成 (E)-1-(4-ethynylphenyl)-2-(4-pyridyl)ethylene
  参考文献：
  名称：

  π-Extended conjugate phenylacetylenes. Synthesis of 4-[(E) and (Z)-2-(4-ethenylphenyl)ethenyl]pyridine. Dimerization, quaternation and formation of charge–transfer complexes

  摘要：

  The conjugate (E)- and (Z)-(4'-pyridylethenyl)-4-phenylethyne (E-4 and Z-4) has been satisfactorily prepared by two different routes: (a) by dehydrohalogenation of 4'-pyridylethenyl-4-phenyi-beta-chloroethene; (b) by the Wittig reaction between p-(iodobenzyl)(triphenyl)phosphine ylide and 4-pyridinecarboxaldehyde, E/Z isomer separation, and cross-coupling with 2-methyl-but-3-yn-2-ol followed the propanone elimination. The Glaser oxidative dimerization of (Z)-4 yields (Z,Z)-1,4-di[(4'-pyridylethenyl)-4-phenyll-buta-1,3-diyne in good yield, (Z,Z)-5. (E,E)-5 was obtained by phase transfer oxidative dimerisation of (E)-4 in presence of their N-methyl salt (E)-10. Mono-and di-N-methylated salts of conjugate (E,E)-5 and (Z,Z)-5, were obtained by quaternation with iodomethane. The (Z,Z)-5 di-N-methylated salt forms charge-transfer complexes with TCNE, TCNQ and TMPD. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01628-9

文献信息

• Hierarchical Synthesis, Structure, and Photophysical Properties of Gallium‐ and Ruthenium‐Porphyrins with Axially Bonded Azo Ligands
  作者：Yueze Gao、Vroni Walter、Michael J. Ferguson、Rik R. Tykwinski

  DOI：10.1002/chem.202002030

  日期：2020.12.15

  The hierarchical synthesis of three porphyrin and four bisporphyrin derivatives is presented. This strategy relies on the incorporation of linkers based on azo moieties appended with pyridyl and/or acetylenic groups that facilitate axial coordination to Ga‐ and Ru‐metalloporphyrins. These porphyrinic systems allow for a quantitative analysis of the effects of diamagnetic anisotropy (DA) by using 1H NMR

  介绍了三种卟啉和四种双卟啉衍生物的分级合成。该策略依赖于结合基于偶氮基的连接基，并附加有吡啶基和/或炔属基团，这些基团有利于Ga-和Ru-金属卟啉的轴向配位。这些卟啉系统可通过1 H NMR光谱和X射线晶体学分析对抗磁各向异性（DA）的影响进行定量分析。实验概述了质子化学位移和与卟啉核的距离之间的简单幂律关系，这证实了先前的理论预测，并表明DA的极限约为2 nm。偶氮连接的卟啉的光物理性质通过紫外/可见光谱分析，表明明显的顺式–仅与Ga卟啉结合的偶氮配体未观察到反式异构化。Ru-卟啉与偶氮配体的结合有利于光开关行为，但该过程面临Ru-卟啉脱羰作用的竞争，只有GaL1Ru记录了明显的开关。
• Syntheses and Reactivity of Ruthenium σ-Pyridylacetylides
  作者：Iuan-Yuan Wu、Jiann T. Lin、Jimmy Luo、Shih-Sheng Sun、Chyi-Shiun Li、Kuan J. Lin、Chiitang Tsai、Chia-Chen Hsu、Jiunn-Lih Lin

  DOI：10.1021/om9610657

  日期：1997.5.1

  Ruthenium sigma-acetylides containing a dangling pyridine were synthesized from the reactions of CpRu(L)(2)Cl (L = PPh3, 1/2 (C5H4PPh2)(2)Fe) with 4-ethynylpyridine, (E)-1-(4-ethynylphenyl)-2-(4-pyridyl)ethylene, or 4-(ethynylphenyl)(4-pyridyl)acetylene in the presence of NH4+PF6- followed by deprotonation with a base. The dangling pyridine can be protonated, methylated, or ligated to tungsten carbonyl fragments. The ruthenium donor to the pyridinium acceptor charge-transfer absorption appears at longer wavelength as the conjugation chain becomes longer. The quadratic hyperpolarizabilities of the methylated derivatives were determined using the hyper Rayleigh scattering method. X-ray analysis was employed to examine the structure of the dinuclear complex Ru(C=CC5H4NW(CO)(4)(PPh3)})(eta(2)-dppf)(eta(5)-C5H5) (dppf = 1,1'-bis(diphenylphosphino)ferrocene).
• PARTICLES AND METHODS FOR LONG WAVELENGTH SERS
  申请人：Cabot Security Materials Inc.

  公开号：EP2433131A1

  公开（公告）日：2012-03-28
• Particles for long wavelength SERS, method of manufacture and method for tagging a material
  申请人：SICPA HOLDING SA

  公开号：EP2433131B1

  公开（公告）日：2016-07-06
• Particles and Methods for Long Wavelength SERS
  申请人：Natan Michael J.

  公开号：US20120057165A1

  公开（公告）日：2012-03-08

  Embodiments include a particle comprising a surface enhanced spectroscopy (SES)-active core and a SES-active reporter molecule associated with the SES-active core wherein said particle has a measurable SES spectrum when excited by incident light having a wavelength of at least 1400 nm. Alternative embodiments include methods of manufacturing said particle and methods of tagging a material with said particle. The particle may include an SES-active core which supports plasmon resonance at a wavelength of at least 1400 nm. The particle may comprise an anisotropic core. The particle may include an SES-active reporter molecule which is resonant at one or more wavelengths greater than or equal to 1400 nm.