trans-4-Methoxy-4'-stilbencarbonsaeure-methylester | 79370-16-4

• 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: trans-4-Methoxy-4'-stilbencarbonsaeure-methylester
• 英文别名: methyl (E)-4-[2-(4-methoxyphenyl)ethenyl]benzoate；methyl 4-[(E)-2-(4-methoxyphenyl)ethenyl]benzoate；methyl 4-[2-(4-methoxyphenyl)-1-ethenyl]benzoate；methyl (E)-4-(4-methoxystyryl)benzoate；(E)-4'-cabomethoxy-4-methoxystilbene
• CAS: 79370-16-4
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: QVFGGQBJJPHYBV-ONEGZZNKSA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  420.4±24.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-4-Methoxy-4'-stilbencarbonsaeure-methylester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以97%的产率得到4'-methoxy-trans-stilbene-4-carboxylic acid
  参考文献：
  名称：

  Alkoxy/halostyryl benzoic acids: Synthesis, crystal structure, and study of mesomorphic and photophysical properties

  摘要：

  Alkoxy/halostyrylbenzoic acids were synthesized and evaluated for their mesomorphic and photophysical properties. The trans geometry of the molecules was established by the presence of large coupling constants in H-1-NMR spectra and confirmed further by X-ray diffraction (XRD) analysis of two of the compounds. The straight-chain acids were found fairly stable showing first sign of decomposition above 290 degrees C. The enantiotropic mesophases could only be studied in acids with seven or more methylene groups in the alkoxy chain. Textures of nematic and smectic phases were exhibited by these acids under polarizing optical microscope. Photophysical behavior of the compounds in solution was also investigated.

  DOI：

  10.1080/15421406.2017.1328215
• 作为产物：
  描述：

  对甲基苯甲酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 xylene 为溶剂， 反应 0.08h， 生成 trans-4-Methoxy-4'-stilbencarbonsaeure-methylester
  参考文献：
  名称：

  Structure of Aggregates of trans-4-Alkoxy-4‘-carboxystilbenes in the Solid State and in Microheterogeneous Media. A Link between the “Unit Aggregate” and Extended Arrays

  摘要：

  Crystals of three 4-alkoxy-4'-carboxy trans-stilbene (ACS) derivatives and a crystal of 4-methoxy-4'-methanoate trans-stilbene have been shown to have structures in which the amphiphilic aromatics are arranged in layers remarkably similar to deposited Langmuir-Blodgett multilayer assemblies. Within each layer there is either a glide or pseudoglide (or herringbone) arrangement of the chromophores very similar to that deduced from physical properties and simulations for structurally related stilbene, azobenzene, and tolan amphiphiles in microheterogeneous media, solution, and Langmuir-Blodgett (LB) films. The fluorescence of the crystals is very similar to that associated with LB films of a water-insoluble amphiphilic ACS that is associated with the aggregate. An analysis of the crystal structure indicates that energetically favorable aromatic-aromatic (edge-face) interaction determines the packing within a layer.

  DOI：

  10.1021/jp962440b

文献信息

• Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides
  作者：Jiandong Liu、Qinghua Ren、Xinghua Zhang、Hegui Gong

  DOI：10.1002/anie.201607959

  日期：2016.12.12

  This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy‐to‐operate nickel‐catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional‐group tolerance. The nickel‐catalytic system displays

  这项工作强调了在温和且易于操作的镍催化反应条件下，通过芳基卤化物与乙烯基溴的还原偶联来合成取代的乙烯基芳烃。广泛使用的芳基卤化物，包括杂芳族化合物和乙烯基溴化物，以中等至优异的收率生产了具有高官能团耐受性的产品。镍催化系统在两个C（sp 2）-卤化物偶合体之间显示出良好的化学选择性，从而证明了不同于其他逐步方案的机理途径。
• Continuous Flow Palladium(II)-Catalyzed Oxidative Heck Reactions with Arylboronic Acids
  作者：Luke R. Odell、Jonas Lindh、Tomas Gustafsson、Mats Larhed

  DOI：10.1002/ejoc.201000063

  日期：2010.4

  Palladium(II)-catalyzed oxidative Heck reactions were investigated under continuous flow conditions. Selective, fast and convenient protocols for the coupling of arylboronic acids with electron-rich and electron-poor olefins were developed by using a commercially available flow reactor.

  在连续流动条件下研究了钯 (II) 催化的氧化 Heck 反应。通过使用市售流动反应器开发了用于将芳基硼酸与富电子和缺电子烯烃偶联的选择性、快速和方便的方案。
• Catalytic Semireduction of Internal Alkynes with All-Metal Aromatic Complexes
  作者：Pierre-Alexandre Deyris、Tatiana Cañeque、Yanlan Wang、Pascal Retailleau、Franca Bigi、Raimondo Maggi、Giovanni Maestri、Max Malacria

  DOI：10.1002/cctc.201500729

  日期：2015.10

  A simple catalytic method involving all‐metal aromatic frameworks as precatalysts ensures an efficient route to (Z)‐alkenes. Aromatic triangular palladium clusters were used to reduce internal alkynes without any trace of the formation of alkane side products. These trinuclear complexes provide a catalytic system that parallels the activity and selectivity of their best mononuclear peers, and the catalyst

  一种简单的催化方法，其中包含全金属芳族骨架作为预催化剂，可确保获得通往（Z）烯烃的有效途径。芳族三角钯簇被用于还原内部炔烃，而没有任何痕量的烷烃副产物形成。这些三核配合物提供了一种催化系统，可与它们最好的单核对等体的活性和选择性相提并论，并且该催化剂可能通过互补机制起作用。
• An Interrupted Pummerer/Nickel-Catalysed Cross-Coupling Sequence
  作者：Miles H. Aukland、Fabien J. T. Talbot、José A. Fernández-Salas、Matthew Ball、Alexander P. Pulis、David J. Procter

  DOI：10.1002/anie.201805396

  日期：2018.7.26

  An interrupted Pummerer/nickel‐catalysed cross‐coupling strategy has been developed and used in the elaboration of styrenes. The operationally simple method can be carried out as a one‐pot process, involves the direct formation of stable alkenyl sulfonium salt intermediates, utilises a commercially available sulfoxide, catalyst, and ligand, operates at ambient temperature, accommodates sp‐, sp2‐, and

  已经开发了一种中断的Pummerer /镍催化的交叉偶联策略，并将其用于苯乙烯的精制。操作简单的方法可以作为一个锅法进行，涉及直接形成稳定的烯基sulf盐中间体，利用市售的亚砜，催化剂和配体，在环境温度下操作，可容纳sp‐，sp 2‐，和sp 3杂交的有机锌偶联伙伴，并通过两个步骤以高收率提供官能化的苯乙烯产品。中断的Pummerer /环化方法也已用于获得碳和杂环烯基sulf盐进行交叉偶联。
• Entangled palladium nanoparticles in resin plugs
  作者：Romain Najman、Jin Ku Cho、Andrew F. Coffey、John W. Davies、Mark Bradley

  DOI：10.1039/b711978j

  日期：——

  Palladium nanoparticles were entrapped within resin plugs and used in a range of ligand-free cross-coupling reactions; the convenient modular format of the resin plug enhanced resin handling and allowed the catalysts to be easily recovered and multiply reused.

  钯纳米颗粒被封装在树脂塞中，并用于一系列无配体的交叉偶联反应；树脂塞的方便模块化格式提高了树脂的处理，并允许催化剂轻松回收和多次重复使用。