2,6-二苯基-4,4'-联吡啶 | 16208-83-6

• 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
• 中文名称: 2,6-二苯基-4,4'-联吡啶
• 英文名称: 4-(pyridine-4-yl)-2,6-diphenylpyridine
• 英文别名: 2,6-Diphenyl-4,4'-bipyridyl；2,6-Diphenyl-4,4'-bipyridine；2,6-diphenyl-4-pyridin-4-ylpyridine
• CAS: 16208-83-6
• 化学式: C₂₂H₁₆N₂
• 分子量: 308.382
• InChiKey: AGVQSEGGWFOUSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-二苯基-4,4'-联吡啶 、 碘甲烷 在 tetrafluoroboric acid 作用下， 生成 4-(1-methylpyridinium-4-yl)-2,6-diphenylpyridine tetrafluoroborate
  参考文献：
  名称：

  Katritzky, Alan R.; Adamson, Jeffrey; Elisseou, E. Michael, Journal of the Chemical Society. Perkin transactions II, 1982, p. 1041 - 1048

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-1-phenyl-3-(pyridin-4-yl)prop-2-en-1-one 在 乙酸铵 、 溶剂黄146 作用下， 反应 4.0h， 以98%的产率得到2,6-二苯基-4,4'-联吡啶
  参考文献：
  名称：

  Kröhnke吡啶：2,4,6-三芳基吡啶的无溶剂合成

  摘要：

  从查尔酮与乙酸铵在无溶剂条件下以优异的收率进行的新颖反应描述了一种2,4,6-三芳基吡啶的简单有效合成方法。

  DOI：

  10.1016/j.tetlet.2006.01.162

文献信息

• Reaction between Guanidine Hydrochloride and Chalcones: An Efficient Solvent-free Synthesis of 2,4,6-Triarylpyridines under Microwave Irradiation
  作者：Mehdi Adib、Bagher Mohammadi、Sahar Rahbari、Peiman Mirzaei

  DOI：10.1246/cl.2008.1048

  日期：2008.10.5

  A series of 2,4,6-triarylpyridines have been synthesized via an efficient solvent-free reaction between guanidine hydrochloride and chalcones under microwave irradiation in excellent yields.

  在微波辐射下，通过盐酸胍和查耳酮之间的高效无溶剂反应合成了一系列 2,4,6-三芳基吡啶，收率极佳。
• Nano-Fe₃O₄–Supported, Hydrogensulfate Ionic Liquid–Catalyzed, One-Pot Synthesis of Polysubstituted Pyridines
  作者：Heshmatollah Alinezhad、Mahmood Tajbakhsh、Neda Ghobadi

  DOI：10.1080/00397911.2015.1041046

  日期：2015.9.2

  Abstract Anchoring 1-methyl-3-(triethoxysilylpropyl) imidazolium chloride onto silica-coated magnetic Fe3O4 particles afforded the corresponding supported ionic liquid. Exchanging the Cl− anion by treating with H2SO4 gave Brønsted ionic liquid 1-methyl-3-(triethoxysilylpropyl) imidazolium hydrogensulfate. The synthesized catalyst was characterized by various techniques such as infrared, x-ray diffraction

  摘要 将 1-甲基-3-(三乙氧基甲硅烷基丙基) 咪唑氯化物锚定在二氧化硅包覆的磁性 Fe3O4 颗粒上得到相应的负载型离子液体。通过用 H2SO4 处理交换 Cl- 阴离子得到 Brønsted 离子液体 1-甲基-3-（三乙氧基甲硅烷基丙基）咪唑鎓硫酸氢盐。通过红外、X 射线衍射、扫描电子显微镜、热重分析和元素分析等多种技术对合成的催化剂进行了表征。结果表明所制备的催化剂具有纳米结构。在无溶剂条件下，通过芳香醛与苯乙酮和乙酸铵以中等至良好产率反应合成多取代吡啶，研究了负载型离子液体的催化活性。该催化剂可以通过施加外部磁场轻松回收，并可重复使用至少七次，而不会降低催化活性。图形概要
• The synthesis of polysubstituted pyridines using nano Fe3O4 supported hydrogensulfate ionic liquid
  作者：Heshmatollah Alinezhad、Mahmood Tajbakhsh、Neda Ghobadi

  DOI：10.1007/s11164-015-1951-3

  日期：2015.11

  Reaction of 1-methylimidazole with 3-(trimethoxysilyl)propyl chloride resulted in formation of 1-methyl-3-(trimethoxysilyl)propyl imidazolium chloride ([pmim]Cl). Anchoring of the ionic liquid on to silica-coated magnetic Fe3O4 particles afforded the corresponding supported ionic liquid MNP-[pmim]Cl. Exchanging the Cl− anion by treatment with H2SO4 gave the Brønsted ionic liquid MNP-[pmim]HSO4. FT-IR, XRD, SEM, TEM, TG/DTG, VSM, and CHN analysis were used to characterize the supported ionic liquid. The results indicated the catalyst was a nanostructure. The catalytic activity of the supported ionic liquid was examined in the synthesis of the polysubstituted pyridines by reaction of aromatic aldehydes, and acetophenones or indan-1-one with ammonium acetate under solvent-free conditions. The catalyst could be easily recovered, by applying an external magnetic field, and reused at least six runs without deterioration of its catalytic activity.

  1-甲基咪唑与3-(三甲氧基硅基)丙基氯的反应生成了1-甲基-3-(三甲氧基硅基)丙基咪唑氯化物（[pmim]Cl）。将该离子液体固定在涂有二氧化硅的磁性Fe3O4颗粒上，得到了相应的支撑离子液体MNP-[pmim]Cl。用H2SO4处理将Cl−阴离子交换为布朗斯特酸性离子液体MNP-[pmim]HSO4。采用FT-IR、XRD、SEM、TEM、TG/DTG、VSM和CHN分析对支撑离子液体进行了表征。结果表明该催化剂为纳米结构。支撑离子液体的催化活性在芳香醛与乙酰苯酮或indan-1-酮与醋酸铵在无溶剂条件下反应合成多取代吡啶的过程中得到了检验。催化剂可以通过施加外部磁场轻松回收，并且在至少六次使用中不损失其催化活性。
• An Efficient Synthesis of 2,4,6-Triarylpyridines via Solvent-Free Reaction between Acetophenoneoximes and Aldehydes
  作者：Mehdi Adib、Shabnam Mahernia、Mohammad Mahdavi

  DOI：10.1055/s-0033-1341109

  日期：——

  An efficient synthesis of 2,4,6-triarylpyridines is described. Heating a mixture of an acetophenoneoxime and an aldehyde under solvent-free conditions afforded Krohnke pyridines in excellent yields. In this method acetophenoneoximes are directly used for the preparation of Krohnke pyridines under metal-free conditions.

  描述了 2,4,6-三芳基吡啶的有效合成。在无溶剂条件下加热苯乙酮​​肟和醛的混合物以优异的产率提供克罗恩克吡啶。在该方法中，苯乙酮肟直接用于在无金属条件下制备克罗恩克吡啶。
• An efficient method for the synthesis of new derivatives of 2,4,6-triarylpyridines as cytotoxic agents
  作者：Bahram Ahmadi Baloutaki、Mohammad Hosein Sayahi、Mohammad Nikpassand、Hassan Kefayati

  DOI：10.1007/s11164-019-04025-6

  日期：2020.2

  New series of 2,4,6-triarylpyridines derivatives 5a–f and 6a–d were designed, synthesized and evaluated for their cytotoxic activity against breast cancer cell lines. Three-component reaction between acetophenones, ammonium acetate and 4-methyl or 2-methylpyridine in the presence of iodine in DMSO lead to title 2,4,6-triarylpyridines. This method allows the simple preparation of the desired products

  设计，合成和评估了新的2,4,6-三芳基吡啶衍生物系列5a-f和6a-d对乳腺癌细胞系的细胞毒活性。在碘中，在DMSO中，苯乙酮，乙酸铵与4-甲基或2-甲基吡啶之间的三组分反应产生标题2,4,6-三芳基吡啶。该方法允许在温和的反应条件下使用容易获得的试剂以良好的收率简单地制备所需产物。研究了合成的化合物对MDA-MB-231，MCF-7和T-47D细胞系的细胞毒活性。与标准药物依托泊苷相比，大多数合成化合物显示出显着的细胞毒性。