2,6-bis(4-ethylphenyl)pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,6-bis(4-ethylphenyl)pyridine
• 化学式: C₂₁H₂₁N
• 分子量: 287.404
• InChiKey: KUPVYFRIARENOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,6-二氯吡啶 、 4-乙基苯硼酸 在 C₂₃H₂₀ClFeN₃Pd 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以70%的产率得到2,6-bis(4-ethylphenyl)pyridine
  参考文献：
  名称：

  源自不对称钳型配体的二茂铁四环化合物：在Suzuki-Miyaura反应过程中生成Pd（0）纳米颗粒的证据，以及在噻唑和异恶唑直接芳基化中的应用†

  摘要：

  合成了新的二茂铁基-Paladacycle配合物家族Pd（L 1）Cl（Pd1）和Pd（L 2）Cl（Pd2），并通过紫外可见，IR，ESI-MS和NMR光谱研究对其进行了表征。Pd1和Pd2的分子结构通过X射线晶体学研究确定。利用苯硼酸和取代的氯苯衍生物研究了Palladacycle催化的Suzuki-Miyaura交叉偶联反应。机理研究证实了催化循环过程中Pd（0）纳米粒子的生成，并通过XPS，SEM和TEM分析对纳米粒子进行了表征。使用这些二茂铁基-palladacycle配合物检测了噻唑和异恶唑衍生物的直接CH芳基化反应。提出了芳基化反应涉及Pd（0）纳米粒子的原位生成的反应模型。

  DOI：

  10.1039/c9dt03465j

文献信息

• Agro-Waste Generated Pd/CAP-Ash Catalyzed Ligand-Free Approach for Suzuki–Miyaura Coupling Reaction
  作者：Rupesh C. Patil、Ashutosh A. Jagdale、Uttam P. Patil、Jeevan S. Ghodake、Sawanta S. Mali、Chang K. Hong、Suresh S. Patil

  DOI：10.1007/s10562-021-03597-6

  日期：2021.12

  Peels (CAP) to ash via thermal treatment, on which Pd(OAc)2 was immobilized easily that produced a low-cost, highly efficient Pd/CAP-ash catalyst. The prepared catalyst was fully characterized by using FT-IR, SEM, EDX, XRF, DSC-TGA, BET, HR-TEM, and XPS techniques. The Pd/CAP-ash catalyst was conveniently applied for the Suzuki–Miyaura coupling reaction under external base free and ligand-free conditions

  摘要 我们通过热处理将农业废弃物奶油苹果皮 (CAP) 转化为灰分，在其上轻松固定 Pd(OAc)2，从而生产出低成本、高效的 Pd/CAP 灰分催化剂。通过使用 FT-IR、SEM、EDX、XRF、DSC-TGA、BET、HR-TEM 和 XPS 技术对制备的催化剂进行了全面表征。Pd/CAP-ash 催化剂可方便地应用于 Suzuki-Miyaura 偶联反应，在无外部碱和无配体的条件下，在水-有机溶剂中以良好到优异的产率生产联苯。我们协议的主要吸引力是钯支持的农业废物材料的应用，该材料易于回收和回收，可在较短的反应时间内提供单和双偶联衍生物。 图形摘要
• Pd-Catalyzed Decarboxylation and Dual C(sp³)–H Functionalization Protocols for the Synthesis of 2,4-Diarylpyridines
  作者：Raghuram Gujjarappa、Nagaraju Vodnala、Mohan Kumar、Chandi C. Malakar

  DOI：10.1021/acs.joc.8b02971

  日期：2019.5.3

  The Pd-catalyzed decarboxylation and dual C(sp3)–H bond functionalization approaches have been described for the preparation of symmetrical and unsymmetrical 2,4-diarylpyridines. The developed transformations were realized using nonactivated aromatic ketones and amino acids as C–N sources. The efficacy of the catalyst and reagent combination drives the transformation toward the formation of desired

  Pd催化的脱羧作用和双重C（sp 3）–H键官能化方法已被描述用于制备对称和不对称的2,4-二芳基吡啶。使用非活化的芳族酮和氨基酸作为C–N来源可以实现发达的转化。催化剂和试剂组合的功效推动了向高产率和高选择性的所需产物形成的转化。所描述的反应条件通过[2 + 2 + 2]环加成诱导了苯丙氨酸的自反应，并最小化了3,5-苯基吡啶作为副产物的形成，而使用甘氨酸作为C–N来源，相应的2， 6-二芳基吡啶是次要产物。
• PROCESS FOR PRODUCTION OF DISULFONIC ACID COMPOUND, ASYMMETRIC MANNICH CATALYST, PROCESS FOR PRODUCTION OF -AMINOCARBONYL DERIVATIVE, AND NOVEL DISULFONATE SALT
  申请人：National University Corporation Nagoya University

  公开号：EP2208722A1

  公开（公告）日：2010-07-21

  Hexamethylphosphoramide (HMPA) was added to a reaction vessel containing (R)-1,1'-binaphthyl-2,2'-dithiol and potassium hydroxide. The vessel was purged with oxygen and stirred at 80°C for 5 days under 7 atmospheres of oxygen. After being cooled to room temperature, the reaction product was purified to yield potassium (R)-1,1'-binaphthyl-2,2'-disulfonate. The (R)-1,1'-binaphthyl-2,2'-disulfonic acid obtained from the disulfonate and 2,6-diphenylpyridine were stirred in acetonitrile, and then the solvent was evaporated under reduced pressure. Subsequently, magnesium sulfate and distilled CH2Cl2 were added to the reaction product, and the mixture was stirred at room temperature for 30 minutes. The resulting solution was cooled to 0°C. Benzaldehyde imine whose nitrogen is protected with Cbz and subsequently acetyl acetone were dropped into the solution over a period of 1 hour. The resulting mixture was further stirred at 0°C for 30 minutes. A corresponding β-aminocarbonyl derivative was thus produced with an yield of 91% and an enantiomeric excess of 90% ee.

  在装有 (R)-1,1'-联萘-2,2'-二硫醇和氢氧化钾的反应容器中加入六甲基磷酰胺（HMPA）。在 7 个大气压的氧气条件下，用氧气吹扫该容器并在 80°C 下搅拌 5 天。冷却至室温后，纯化反应产物，得到(R)-1,1'-联萘-2,2'-二磺酸钾。将从二磺酸盐中得到的 (R)-1,1'-联萘-2,2'-二磺酸和 2,6-二苯基吡啶在乙腈中搅拌，然后减压蒸发溶剂。随后，向反应产物中加入硫酸镁和蒸馏过的 CH2Cl2，并在室温下搅拌混合物 30 分钟。所得溶液冷却至 0°C。在 1 小时内向溶液中滴入氮被 Cbz 保护的苯甲醛亚胺，随后滴入乙酰丙酮。所得混合物在 0°C 下继续搅拌 30 分钟。由此制得相应的 β-氨基羰基衍生物，收率为 91%，对映体过量率为 90%ee。
• PROCESS FOR MANUFACTURING DISULFONIC ACID COMPOUND, ASYMMETRIC MANNICH CATALST, PROCESS FOR MANUFACTURING BETA-AMINOCARBONYL DERIVATIVE, AND NOVEL DISULFONATE
  申请人：Ishihara Kazuaki

  公开号：US20100249431A1

  公开（公告）日：2010-09-30

  Hexamethylphosphoramide (HMPA) was added to a reaction vessel containing (R)-1,1′-binaphthyl-2,2′-dithiol and potassium hydroxide. The vessel was purged with oxygen and stirred at 80° C. for 5 days under 7 atmospheres of oxygen. After being cooled to room temperature, the reaction product was purified to yield potassium (R)-1,1′-binaphthyl-2,2′-disulfonate. The (R)-1,1′-binaphthyl-2,2′-disulfonic acid obtained from the disulfonate and 2,6-diphenylpyridine were stirred in acetonitrile, and then the solvent was evaporated under reduced pressure. Subsequently, magnesium sulfate and distilled CH 2 Cl 2 were added to the reaction product, and the mixture was stirred at room temperature for 30 minutes. The resulting solution was cooled to 0° C. Benzaldehyde imine whose nitrogen is protected with Cbz and subsequently acetyl acetone were dropped into the solution over a period of 1 hour. The resulting mixture was further stirred at 0° C. for 30 minutes. A corresponding β-aminocarbonyl derivative was thus produced with an yield of 91% and an enantiomeric excess of 90% ee.
• Ferrocenyl palladacycles derived from unsymmetrical pincer-type ligands: evidence of Pd(0) nanoparticle generation during the Suzuki–Miyaura reaction and applications in the direct arylation of thiazoles and isoxazoles
  作者：Ankur Maji、Anshu Singh、Aurobinda Mohanty、Pradip K. Maji、Kaushik Ghosh

  DOI：10.1039/c9dt03465j

  日期：——

  Mechanistic investigation authenticated the generation of Pd(0) nanoparticles during the catalytic cycle and the nanoparticles were characterized by XPS, SEM and TEM analysis. Direct C–H arylation of thiazole and isoxazole derivatives employing these ferrocenyl-palladacycle complexes was examined. The reaction model for the arylation reaction implicating the in situ generation of Pd(0) nanoparticles was

  合成了新的二茂铁基-Paladacycle配合物家族Pd（L 1）Cl（Pd1）和Pd（L 2）Cl（Pd2），并通过紫外可见，IR，ESI-MS和NMR光谱研究对其进行了表征。Pd1和Pd2的分子结构通过X射线晶体学研究确定。利用苯硼酸和取代的氯苯衍生物研究了Palladacycle催化的Suzuki-Miyaura交叉偶联反应。机理研究证实了催化循环过程中Pd（0）纳米粒子的生成，并通过XPS，SEM和TEM分析对纳米粒子进行了表征。使用这些二茂铁基-palladacycle配合物检测了噻唑和异恶唑衍生物的直接CH芳基化反应。提出了芳基化反应涉及Pd（0）纳米粒子的原位生成的反应模型。