(E)-4-(4-bromostyryl)benzonitrile | 144092-35-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-4-(4-bromostyryl)benzonitrile
• 英文别名: (e)-4-(4-Bromostyryl)benzonitrile；4-[(E)-2-(4-bromophenyl)ethenyl]benzonitrile
• CAS: 144092-35-3
• 化学式: C₁₅H₁₀BrN
• 分子量: 284.155
• InChiKey: ZSHOMMTUBODLLN-OWOJBTEDSA-N

物化性质

• 熔点：
  192-194 °C
• 沸点：
  418.0±24.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4'-氨基苯并-15-冠-5-醚 、 (E)-4-(4-bromostyryl)benzonitrile 在 tris(dibenzylideneacetone)dipalladium (0) R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 4-[(E)-2-[4-(2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-ylamino)phenyl]ethenyl]benzonitrile
  参考文献：
  名称：

  Bimodal fluorescence signaling based on control of the excited-state conformational twisting and the ground-state protonation processes

  摘要：

  Amino-based fluoroionophores 1 and 2 can selectively sense alkaline earth metal ions in MeCN under both neutral and acidic conditions by different signaling mechanisms. The fluoroionophoric behavior for the neutral probes is characterized by an 'off-on' photoinduced electron transfer (PET)-like fluorescence intensity response due to a switching from a twisted internal charge transfer (TICT) to a planar internal charge transfer (PICT) state. For the protonated probes (i.e., 1/H+ and 2/H+), the fluorescing species is the localized stilbene fluorophores, but dual fluorescence is induced upon metal-ion recognition through a deprotonation process. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.02.120
• 作为产物：
  描述：

  1-溴-4-[2-(4-溴苯基)乙基]苯 在 吡啶 、 溴 、 溶剂黄146 作用下， 生成 (E)-4-(4-bromostyryl)benzonitrile
  参考文献：
  名称：

  1.二苯烷的溴化和一些二苯乙烯衍生物的制备。第一部分。αβ-二苯乙烷

  摘要：

  DOI：

  10.1039/jr9430000001

文献信息

• Photophysical Properties of Silyl‐Substituted Stilbene Derivatives
  作者：Hajime Maeda、Ryo Horikoshi、Minoru Yamaji、Taniyuki Furuyama、Masahito Segi

  DOI：10.1002/ejoc.202000397

  日期：2020.6.23

  Absorption and fluorescence properties of silyl‐substituted stilbenes were investigated. The derivative in which four Me3Si groups were introduced at the ortho positions did not fluoresce at room temperature. The para bis‐Me3SiC≡C‐substituted analog has a high fluorescence quantum yield (0.95). The stilbene containing Ph2N and Me3SiC≡C groups exhibited solvatofluorochromism while maintaining a good

  研究了甲硅烷基取代的斯蒂苯酯的吸收和荧光性质。在邻位引入四个Me 3 Si基的衍生物在室温下不发荧光。的对位双-ME 3 SiC≡C取代类似物具有高荧光量子产率（0.95）。含pH值茋2 N和我3 SiC≡C组表现出solvatofluorochromism同时保持良好的发射量子产率（0.50）。
• Palladium-Catalysed Desulfitative Heck Reaction Tolerant to Aryl Carbon–Halogen Bonds for Access to (Poly)halo-Substituted Stilbene or Cinnamate Derivatives
  作者：Ridha Salem、Henri Doucet、Aymen Skhiri、Jean-Francois Soulé

  DOI：10.1055/s-0035-1560449

  日期：——

  (poly)halo-substituted benzenesulfonyl chlorides with alkenes was investigated. Styrene or acrylates in the presence of bromo- or iodobenzenesulfonyl chlorides and a phosphine-free palladium catalyst were found to afford the expected β-arylated Heck type products with complete regio- and stereoselectivities. The reaction tolerates a variety of substituents on the halobenzenesulfonyl chloride. Moreover, no cleavage

  摘要 研究了（多）卤代苯磺酰氯与烯烃的钯催化脱硫Heck型反应。发现在溴或碘苯磺酰氯存在下，苯乙烯或丙烯酸酯和无膦的钯催化剂可提供具有完全区域和立体选择性的预期的β-芳基化的Heck型产物。该反应可耐受卤代苯磺酰氯上的各种取代基。此外，在这些反应过程中未观察到C–Br和C–I键的裂解，从而允许进一步转化。使用4-溴苯磺酰氯作为中心单元，连续的脱硫Heck型反应，然后由钯催化的直接芳基化仅需两个步骤即可制备杂芳基二苯乙烯衍生物。 研究了（多）卤代苯磺酰氯与烯烃的钯催化脱硫Heck型反应。发现在溴或碘苯磺酰氯存在下，苯乙烯或丙烯酸酯和无膦的钯催化剂可提供具有完全区域和立体选择性的预期的β-芳基化的Heck型产物。该反应可耐受卤代苯磺酰氯上的各种取代基。此外，在这些反应过程中未观察到C–Br和C–I键的裂解，从而允许进一步转化。使用4-溴苯磺酰氯作为中心单元，连续的脱硫Heck型反应，然后由钯催
• Unsymmetrical <i>E</i>-Alkenes from the Stereoselective Reductive Coupling of Two Aldehydes
  作者：Keyhan Esfandiarfard、Juri Mai、Sascha Ott

  DOI：10.1021/jacs.7b00428

  日期：2017.3.1

  The unprecedented formation of unsymmetrical alkenes from the intermolecular reductive coupling of two different aldehydes is described. In contrast to the McMurry reaction which affords statistical product mixtures, selectivity in the reported procedure is achieved by a sequential ionic mechanism in which a first aldehyde is reacted with a phosphanylphosphonate to afford a phosphaalkene intermediate

  描述了由两种不同醛的分子间还原偶联形成的前所未有的不对称烯烃。与提供统计产物混合物的 McMurry 反应相反，报告程序中的选择性是通过顺序离子机制实现的，其中第一个醛与膦酰基膦酸酯反应以提供磷烯烃中间体，该中间体在被氢氧化物活化后与第二个反应醛到不对称的 E-烯烃。所述反应不含过渡金属并且在环境温度下在几分钟内以良好至极好的总产率进行。这是一种使用原料醛直接生产含 C=C 双键产品的新方法，可能会影响未来化学家对多步合成序列的看法。
• Spectroscopic Correlations between Supermolecules and Molecules. Anatomy of the Ion-Modulated Electronic Properties of the Nitrogen Donor in Monoazacrown-Derived Intrinsic Fluoroionophores
  作者：Jye-Shane Yang、Chung-Yu Hwang、Chia-Chun Hsieh、Shih-Yi Chiou

  DOI：10.1021/jo035462k

  日期：2004.2.1

  The synthesis, absorption and emission spectra, fluorescence quantum yields, and fluorescence lifetimes of three compound series of trans-4,4'-disubstituted aminostilbenes (1-3) are reported. The chromo-/fluoroionophoric behavior of the monoaza-15-crown-5- (A15C5) and monoaza-18-crown-6 (A18C6)-derived species (1A(5)-3A(5) and 1A(6)-3A(6)) in acetonitrile and dichloromethane are also investigated. Great similarities in electronic spectroscopic properties (chemical shifts, wavelength, intensity, and lifetime) between the metal ion-complexed supermolecules and the corresponding chloro-substituted molecules have been observed: namely, 1A(5)/Ca2+-3A(5)/Ca2+ similar to 1A(6)/Ba2+-3A(6)/ Ba(2+)similar to 1C-3C in acetonitrile and 1A(5)/Na+-2A(5)/Na+ similar to 1A(6)/K+-2A(6)/K+ similar to 1C-2C in dichloromethane. Such spectroscopic correlations allow us to define the metal ion-modulated electronic character of the azacrown nitrogen atom in the ground and excited states and, in turn, to gain insights into the observed fluoroionophoric behavior of these probes in terms of the size and direction of fluorescence shifts and intensity variations.
• Design of π-Conjugated Organic Materials for One-Dimensional Energy Transport in Nanochannels
  作者：Juan Carlos Sancho-García、Jean-Luc Brédas、David Beljonne、Jérôme Cornil、Roberto Martínez-Álvarez、Michael Hanack、Lars Poulsen、Johannes Gierschner、Hans-Georg Mack、Hans-Joachim Egelhaaf、Dieter Oelkrug

  DOI：10.1021/jp045364i

  日期：2005.3.1

  Various end-substituted distyrylbenzenes have been synthesized to serve as guest molecules in inclusion compounds to promote efficient energy transport along one-dimensional channels. Their optical and photophysical properties have been characterized at both experimental and theoretical levels. All molecules display a large transition dipole moment between the ground state and lowest excited state and hence a short radiative lifetime (on the order of 1-2 ns). They also exhibit a large spectral overlap between the emission and absorption spectra, which enables efficient energy transport between molecules arranged in a head-to-tail configuration in nanochannels. Hopping rates on the order of 10(12) s(-1) are calculated at a full quantum-chemical level; this is much larger than the radiative lifetimes and opens the way for energy migration over large distances. Changes in the nature of the terminal substituents are found to modulate the optical properties weakly but to impact significantly the energy transfer rates.