2,6-bis(4-oxide-6-phenyl-1,2,4-triazin-3-yl)pyridine | 460348-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 2,6-bis(4-oxide-6-phenyl-1,2,4-triazin-3-yl)pyridine
• 英文别名: 2,6-bis(6-phenyl-1,2,4-triazin-3-yl 4-oxide)pyridine；4-Oxido-3-[6-(4-oxido-6-phenyl-1,2,4-triazin-4-ium-3-yl)pyridin-2-yl]-6-phenyl-1,2,4-triazin-4-ium
• CAS: 460348-45-2
• 化学式: C₂₃H₁₅N₇O₂
• 分子量: 421.418
• InChiKey: CJRGICHFTNJHCV-UHFFFAOYSA-N

物化性质

• 沸点：
  808.8±75.0 °C(predicted)
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,6-bis(4-oxide-6-phenyl-1,2,4-triazin-3-yl)pyridine 以 氯仿 、 甲苯 为溶剂， 反应 6.5h， 生成 6,6''-dicyano-5,5''-diphenyl-2,2',6',2''-terpyridine
  参考文献：
  名称：

  A new route to 6,6′′-dicyano-2,2′:6′,2′′-terpyridines and their complexes with Ni(II)

  摘要：

  A new methodology for the synthesis of functionalised 2,2':6',2"-terpyridine systems is suggested: sequential synthesis of the heterocyclic assemblies based on the 1,2,4-triazine ring, direct introduction of the cyano group in the 1,2,4-triazine ring and the transformation of the latter to a pyridine ring via an aza-Diels-Alder reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00951-6
• 作为产物：
  描述：

  吡啶-2,6-二甲醛 在 lead(II,IV) oxide 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 2,6-bis(4-oxide-6-phenyl-1,2,4-triazin-3-yl)pyridine
  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

• Carborane-Functionalized Polyaza Aromatic Ligands:  Synthesis, Crystal Structure, and a Copper(II) Complex
  作者：Anton M. Prokhorov、Dmitry N. Kozhevnikov、Vladimir L. Rusinov、Oleg N. Chupakhin、Ivan V. Glukhov、Mikhail Yu. Antipin、Olga N. Kazheva、Anatolii N. Chekhlov、Oleg A. Dyachenko

  DOI：10.1021/om051058v

  日期：2006.6.1

  A consecutive aromatic nucleophilic substitutions of hydrogen in 1,2,4-triazine 4-oxides and an aza Diels−Alder reaction is a versatile route to carborane-functionalized bi- and terpyridines and their 1,2,4-triazine analogues. The heterocycles facilitate deboronation of the substituted carboranes, and the carborane moiety has a significant influence on the coordination properties of the ligands as

  在1,2,4-三嗪4-氧化物和aza Diels-Alder反应中进行的连续氢亲核取代反应是通向碳硼烷官能化的联吡啶和三联吡啶及其1,2,4-三嗪类似物的通用途径。杂环促进取代的碳硼烷的脱硼，并且碳硼烷部分也对配体的配位性质具有重要影响。
• A new route to 6,6′′-dicyano-2,2′:6′,2′′-terpyridines and their complexes with Ni(II)
  作者：Dmitry N. Kozhevnikov、Valery N. Kozhevnikov、Tatiana V. Nikitina、Vladimir L. Rusinov、Oleg N. Chupakhin、Igor L. Eremenko、Grigory G. Aleksandrov

  DOI：10.1016/s0040-4039(02)00951-6

  日期：2002.7

  A new methodology for the synthesis of functionalised 2,2':6',2"-terpyridine systems is suggested: sequential synthesis of the heterocyclic assemblies based on the 1,2,4-triazine ring, direct introduction of the cyano group in the 1,2,4-triazine ring and the transformation of the latter to a pyridine ring via an aza-Diels-Alder reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.