5-nitro-2-styrylpyridine | 1357165-74-2

• 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: 5-nitro-2-styrylpyridine
• 英文别名: 3-nitro-6-styrylpyridine；2-(2-phenylethenyl)-5-nitropyridine；5-Nitro-2-(2-phenylethenyl)pyridine
• CAS: 1357165-74-2
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: XWIUJOODUKEKIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氯-5-硝基吡啶 、 [(E)-2-苯基乙烯基]硼酸 在 potassium phosphate monohydrate 、 palladium diacetate 、 N₂Phos 作用下， 以 水 、 甲苯 为溶剂， 反应 16.0h， 以93%的产率得到5-nitro-2-styrylpyridine
  参考文献：
  名称：

  N2Phos –一种易于制备的高效配体，设计用于水中ppm级Pd催化的Suzuki-Miyaura交叉偶联

  摘要：

  一种新型的含钯芳基配体的活性钯催化剂，用于ppm级的Suzuki-Miyaura偶联，可通过胶束反应介质水溶液进行。包括芳基/杂芳基溴化物的各种各样的官能化底物是可取的，尤其是氯化物。在低钯载量（1000-2500 ppm或0.10-0.25 mol％）下，催化系统既通用又高效。密度泛函理论计算表明，在n表示更大的空间拥塞2 PHOS诱导周围的Pd中心增加空间拥挤，帮助动摇2:1配体的Pd（0）配合物更对于N 2 PHOS比EvanPhos（和体积更小的配体） ，从而有利于形成1：1配体– Pd o 在芳基氯化物的氧化加成反应中更具活性的络合物。

  DOI：

  10.1039/d0sc00968g

文献信息

• Metal-free Synthesis of 2-Alkenyl/Alkynyl-5-nitropyridines Using a Three-component Ring Transformation
  作者：Song Thi Le、Haruyasu Asahara、Nagatoshi Nishiwaki

  DOI：10.1246/cl.150045

  日期：2015.6.5

  A metal-free, facile, and efficient protoco lf or synthesizing a series of 2-alkenyl/alkynyl-5-nitropyridines was developed by using a three-component ring transformation of 1-methyl-3,5-dinitro-2-pyridone with α,β-unsaturated ketones and ammonium acetate. As 2-alkenyl/alkynyl-5-nitropyridines are not easily prepared by Heck or Sonogashira reactions, this method will be a supplementary to these reactions

  通过使用 1-甲基-3,5-二硝基-2-吡啶酮的三组分环转化，开发了一种不含金属、简便且高效的方案或合成一系列 2-烯基/炔基-5-硝基吡啶。 α,β-不饱和酮和醋酸铵。由于 Heck 或 Sonogashira 反应不容易制备 2-烯基/炔基-5-硝基吡啶，因此该方法将是这些反应的补充。
• Palladium Supported on Oleic Acid-coated Magnetic Nanoparticle as an Efficient Catalyst for Heck Coupling Reaction in Aqueous Media
  作者：Ezzat Rafiee、Ali Ataei、Mohammad Joshaghani

  DOI：10.2174/1570178611666140815214322

  日期：2014.11.17

  A magnetically recoverable heterogeneous catalyst was synthesized by immobilization of Pd on the surface of oleic acid coated Fe3O4 nanoparticle. This catalyst was used for Heck coupling reaction of styrene with various aryl halides in aqueous media. The catalyst /product separation could be easily achieved with external magnetic field.

  一种可通过磁性恢复的异质催化剂通过将钯固定在表面涂有油酸的Fe3O4纳米颗粒上合成。该催化剂用于在水相媒介中将苯乙烯与各种芳基卤化物进行赫克偶联反应。催化剂/产品的分离可以通过外部磁场轻松实现。
• Combination of palladium and oleic acid coated-magnetite particles: Characterization and using in Heck coupling reaction with magnetic recyclability
  作者：Ezzat Rafiee、Ali Ataei、Shirin Nadri、Mohammad Joshaghani、Sara Eavani

  DOI：10.1016/j.ica.2013.09.042

  日期：2014.1

  The magnetic Fe3O4 nanoparticles were prepared by co-precipitation method and coated with oleic acid. The oleic acid coated Fe3O4 (Fe@OA) particles were used for the immobilization of palladium particles to produce Fe@OA-Pd. Catalyst was characterized by FTIR, XRD, SEM, TEM, VSM, elemental analysis and laser particle size analyzer. The catalytic behavior of Fe@OA-Pd nano particles was measured by the Heck coupling reaction of the various aryl halides (Ar-Br, Ar-Cl) with styrene. With respect to the electron-rich, electron-neutral, and electron-poor aryl halide, they reacted with styrene smoothly to provide the corresponding arylated olefins products in high to excellent yields in most cases. The magnetic catalyst was reused without loss of its high catalytic activity and low Pd leaching after four cycles. Metal leaching of the catalyst was further investigated by ICP-AES and AAS. (C) 2013 Elsevier B.V. All rights reserved.