6-cyano-5-phenyl-2,2'-bipyridine | 453556-98-4

• 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: 6-cyano-5-phenyl-2,2'-bipyridine
• 英文别名: 3-Phenyl-6-pyridin-2-ylpyridine-2-carbonitrile
• CAS: 453556-98-4
• 化学式: C₁₇H₁₁N₃
• 分子量: 257.294
• InChiKey: BIHFGGJITUVKNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-cyano-5-phenyl-2,2'-bipyridine 以 甲醇 、 水 为溶剂， 生成 [Cu(5-phenyl-2,2'-bipyridine-6-carboxylate)Cl]
  参考文献：
  名称：

  CuCl2 induced reactions of 6-ethynyl- and 6-cyano-5-aryl-2,2′-bipyridines with various N- and O-nucleophiles in comparison with the reactions of relative 1,2,4-triazines

  摘要：

  Meanwhile 5-aryl-6-cyano-2,2'-bipyridines are very stable towards various nucleophiles, addition copper(II) chloride to the reactional mixture facilitates nucleophilic addition to the cyano group dramatically. The cyanobipyridines react easily with water, methanol, ethanolamine in the presence of CuCl2 yielding well-crystallized complexes containing carboxylates, carboximidates or carboxamidines as ligands. 5-Cyano-1,2,4-triazines are more active in the reactions due to higher electron-withdrawing properties of this heterocycle. Due to the same reason acetylene moiety of 5-ethynyl-3-pyridyl-1,2,4-triazine adds water quite easily but in the presence of copper chloride as well. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.02.016
• 作为产物：
  描述：

  2,5-Norbornadiene 、 6-phenyl-3-(2-pyridyl)-1,2,4-triazine-5-carbonitrile 以 甲苯 为溶剂， 反应 12.0h， 以95%的产率得到6-cyano-5-phenyl-2,2'-bipyridine
  参考文献：
  名称：

  A Versatile Strategy for the Synthesis of Functionalized 2,2‘-Bi- and 2,2‘:6‘,2‘ ‘-Terpyridines via Their 1,2,4-Triazine Analogues

  摘要：

  A general synthetic route for the synthesis of functionalized bi- and terpyridines is reported. Functionalized 1,2,4-triazene 4-oxides 7 and 8-obtained from the reaction of hydrazones 1 with pyridine aldehydes and followed by oxidation-are functionalized by introduction of a cyano group via nucleophilic aromatic substitution. The thus-obtained 5-cyano-1,2,4-triazines 9 and 10 undergo facile inverse-electron-demand Diels-Alder reactions with enamines and alkenes to yield functionalized bi- and terpyridines, respectively. The substituent at position 6 of the 1,2,4-triazene 4-oxides must be aromatic or heteroaromatic in order to allow their facile synthesis, but other substituents and reagents may vary. Each step of the synthetic route allows diversification, which makes the approach particularly useful for the facile synthesis of a large variety of functionalized bi- and terpyridines.

  DOI：

  10.1021/jo0267955

文献信息

• Kozhevnikov, Dmitry N.; Kozhevnikov, Valery N.; Nikitina, Tatiana V., Mendeleev Communications, 2002, vol. 12, # 1, p. 30 - 32
  作者：Kozhevnikov, Dmitry N.、Kozhevnikov, Valery N.、Nikitina, Tatiana V.、Rusinov, Vladimir L.、Chupakhin, Oleg N.、Neunhoeffer, Hans

  DOI：——

  日期：——
• A Versatile Strategy for the Synthesis of Functionalized 2,2‘-Bi- and 2,2‘:6‘,2‘ ‘-Terpyridines <i>via</i> Their 1,2,4-Triazine Analogues
  作者：Valery N. Kozhevnikov、Dmitry N. Kozhevnikov、Tatiana V. Nikitina、Vladimir L. Rusinov、Oleg N. Chupakhin、Manfred Zabel、Burkhard König

  DOI：10.1021/jo0267955

  日期：2003.4.1

  A general synthetic route for the synthesis of functionalized bi- and terpyridines is reported. Functionalized 1,2,4-triazene 4-oxides 7 and 8-obtained from the reaction of hydrazones 1 with pyridine aldehydes and followed by oxidation-are functionalized by introduction of a cyano group via nucleophilic aromatic substitution. The thus-obtained 5-cyano-1,2,4-triazines 9 and 10 undergo facile inverse-electron-demand Diels-Alder reactions with enamines and alkenes to yield functionalized bi- and terpyridines, respectively. The substituent at position 6 of the 1,2,4-triazene 4-oxides must be aromatic or heteroaromatic in order to allow their facile synthesis, but other substituents and reagents may vary. Each step of the synthetic route allows diversification, which makes the approach particularly useful for the facile synthesis of a large variety of functionalized bi- and terpyridines.
• CuCl2 induced reactions of 6-ethynyl- and 6-cyano-5-aryl-2,2′-bipyridines with various N- and O-nucleophiles in comparison with the reactions of relative 1,2,4-triazines
  作者：Anton M. Prokhorov、Pavel A. Slepukhin、Dmitry N. Kozhevnikov

  DOI：10.1016/j.jorganchem.2008.02.016

  日期：2008.5

  Meanwhile 5-aryl-6-cyano-2,2'-bipyridines are very stable towards various nucleophiles, addition copper(II) chloride to the reactional mixture facilitates nucleophilic addition to the cyano group dramatically. The cyanobipyridines react easily with water, methanol, ethanolamine in the presence of CuCl2 yielding well-crystallized complexes containing carboxylates, carboximidates or carboxamidines as ligands. 5-Cyano-1,2,4-triazines are more active in the reactions due to higher electron-withdrawing properties of this heterocycle. Due to the same reason acetylene moiety of 5-ethynyl-3-pyridyl-1,2,4-triazine adds water quite easily but in the presence of copper chloride as well. (C) 2008 Elsevier B.V. All rights reserved.