2,4-diphenyl-6-(p-tolyl)pyridine | 71103-78-1

• 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: 2,4-diphenyl-6-(p-tolyl)pyridine
• 英文别名: 2-(4-Methylphenyl)-4,6-diphenylpyridine
• CAS: 71103-78-1
• 化学式: C₂₄H₁₉N
• 分子量: 321.422
• InChiKey: FPGVAZYUJMQMHP-UHFFFAOYSA-N

物化性质

• 熔点：
  121 °C(Solv: ethanol (64-17-5))
• 沸点：
  467.5±14.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  3-phenyl-1-p-tolylprop-2-en-1-one 在 高氯酸 、 氨 作用下， 生成 2,4-diphenyl-6-(p-tolyl)pyridine
  参考文献：
  名称：

  Fischer, Gerhard W.; Herrmann, Michael, Journal fur praktische Chemie (Leipzig 1954), 1984, vol. 326, # 2, p. 287 - 302

  摘要：

  DOI：

文献信息

• A “one pot” synthesis of polysubstituted pyridines from metallated alkylphosphonates, nitriles and α,β-unsaturated ketones
  作者：Francisco Palacios、Ana M. Ochoa de Retana、Julen Oyarzabal

  DOI：10.1016/0040-4039(96)00850-7

  日期：1996.6

  A simple and efficient synthesis of polysubstituted pyridines is described. The key step is based on the regioselective addition of lithiated β-enaminophosphonates 5 to unsaturated carbonyl compounds 3. Pyridines 1 can also be obtained in “one pot” reaction from phosphonates 6 when these compounds are metallated followed by addition of nitriles and unsaturated carbonyl compounds.

  描述了一种简单有效的多取代吡啶的合成方法。关键步骤是基于将锂化的β-烯氨基膦酸酯5的区域选择性加成到不饱和羰基化合物3上。当这些化合物金属化后，通过添加腈和不饱和羰基化合物，也可在“一锅”反应中从膦酸酯6获得吡啶1。
• Regiocontrolled synthesis of 2,4,6-triarylpyridines from methyl ketones, electron-deficient acetylenes and ammonium acetate
  作者：Dmitrii A. Shabalin、Marina Yu. Dvorko、Elena Yu. Schmidt、Boris A. Trofimov

  DOI：10.1039/d1ob00193k

  日期：——

  A novel one-pot two-step approach for the synthesis of 2,4,6-triarylpyridines via t-BuOK/DMSO-promoted C-vinylation of a variety of methyl ketones with electron-deficient acetylenes (alkynones) followed by a cyclization of the in situ generated unsaturated 1,5-dicarbonyl species with ammonium acetate has been developed. This approach possesses competitive advantages such as high regioselectivity, available

  一种新颖的一锅两步方法，通过t -BuOK / DMSO促进的多种甲基酮的C-乙烯基与电子缺陷型乙炔（炔烃）的合成，然后环化环戊二烯，合成2,4,6-三芳基吡啶在原位用乙酸铵生成的不饱和的1,5-二羰基物种已经研制成功。该方法具有竞争优势，例如区域选择性高，可用的起始原料以及不存在过渡金属催化剂，氧化剂和不良副产物。三取代，四取代和稠合吡啶的合成证明了该开发方法的广泛合成效用。
• Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines
  作者：Wei Wen Tan、Yew Jin Ong、Naohiko Yoshikai

  DOI：10.1002/anie.201704378

  日期：2017.7.3

  A copper-catalyzed condensation reaction of oxime acetates and α,β-unsaturated ketimines to give pyridine derivatives is reported. The reaction features mild conditions, high functional-group compatibility, and high regioselectivity with respect to unsymmetrical oxime acetates, thus allowing the preparation of a wide range of polysubstituted pyridines, many of which are not readily accessible by conventional

  据报道，乙酸肟肟和α，β-不饱和酮亚胺在铜催化下缩合反应生成吡啶衍生物。该反应具有温和的条件，相对于不对称肟肟酸酯的高官能团相容性和高的区域选择性，因此可以制备多种多取代的吡啶，其中许多不易通过常规缩合方法获得。
• A new route to triphenylpyridines utilizing ketoximes as building blocks via cascade reactions under iron-organic framework catalysis
  作者：Vu H.H. Nguyen、Son H. Doan、Tram T. Van、Phuc H. Pham、Tran T.N. Nguyen、Ngoc N. Nguyen、Thach N. Tu、Nam T.S. Phan

  DOI：10.1002/aoc.4841

  日期：2019.4

  framework VNU‐20 was utilized as a heterogeneous catalyst for cascade reactions between ketoximes and dibenzyl ether to produce 2,4,6‐triphenylpyridines. Additionally, benzyl alcohol and (dimethoxymethyl)benzene could be used as an alternative starting materials for the transformation. The oxidant exhibited a remarkable impact on the reactions, and di‐tert‐butylperoxide was the most appropriate candidate

  铁基金属有机框架VNU-20被用作酮肟和二苄基醚之间的级联反应的异质催化剂，以生产2,4,6-三苯基吡啶。另外，苯甲醇和（二甲氧基甲基）苯可以用作替代的起始原料。氧化剂对反应有显着影响，而过氧化二叔丁基是最合适的选择。VNU-20显示出比许多均相和非均相催化剂更高的效率。该催化剂可用于级联反应，而催化活性没有明显降低。该转化是新的，并且将利用酮肟作为构建基团为三苯基吡啶提供替代途径。
• Synthesis of triphenylpyridines <i>via</i> an oxidative cyclization reaction using Sr-doped LaCoO₃ perovskite as a recyclable heterogeneous catalyst
  作者：Thu N. M. Le、Son H. Doan、Phuc H. Pham、Khang H. Trinh、Tien V. Huynh、Tien T. T. Tran、Minh-Vien Le、Tung T. Nguyen、Nam T. S. Phan

  DOI：10.1039/c9ra04096j

  日期：——

  strontium-doped lanthanum cobaltite perovskite was prepared via a gelation and calcination approach and used as a heterogeneous catalyst for the synthesis of triphenylpyridines via the cyclization reaction between ketoximes and phenylacetic acids. The transformation proceeded via the oxidative functionalization of the sp3 C–H bond in phenylacetic acid. The La0.6Sr0.4CoO3 catalyst demonstrated a superior performance

  通过凝胶化和煅烧的方法制备了La 0.6 Sr 0.4 CoO 3锶掺杂的钴酸镧钙钛矿，并将其用作通过酮肟和苯乙酸之间的环化反应合成三苯基吡啶的非均相催化剂。该转化是通过苯乙酸中 sp 3 C-H 键的氧化官能化进行的。 La 0.6 Sr 0.4 CoO 3催化剂表现出优于原始LaCoCO 3以及一系列均相和非均相催化剂的性能。此外，La 0.6 Sr 0.4 CoO 3催化剂很容易回收和再利用，而其催化效率没有明显下降。据我们所知，酮肟与容易获得的苯乙酸的组合是新颖的。