2,6-bis-(5,6-dimethyl-[1,2,4]triazin-3-yl)-pyridine | 35171-27-8

• 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-(5,6-dimethyl-[1,2,4]triazin-3-yl)-pyridine
• 英文别名: 2,6-bis(5,6-dimethyl-1,2,4-triazin-3-yl)pyridine；5,6-dimethyl-2,6-bis(1,2,4-triazin-3-yl)pyridine；bis(5,6-dimethyl-1,2,4-triazinyl)pyridine；MeBTP；5,6,5',6'-tetramethyl-3,3'-pyridine-2,6-diyl-bis-[1,2,4]triazine；tetramethyl BTP；3-[6-(5,6-dimethyl-1,2,4-triazin-3-yl)pyridin-2-yl]-5,6-dimethyl-1,2,4-triazine
• CAS: 35171-27-8
• 化学式: C₁₅H₁₅N₇
• 分子量: 293.331
• InChiKey: YFVCCSHCOVDQBH-UHFFFAOYSA-N

物化性质

• 沸点：
  605.6±65.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  90.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,6-bis-(5,6-dimethyl-[1,2,4]triazin-3-yl)-pyridine 、 cerium triflate 以 吡啶 为溶剂， 以94%的产率得到[Ce(2,6-bis(5,6-dimethyl-1,2,4-triazin-3-yl)pyridine)3](CF3SO3)3
  参考文献：
  名称：

  The affinity and selectivity of terdentate nitrogen ligands towards trivalent lanthanide and uranium ions viewed from the crystal structures of the 1 ∶ 3 complexes

  摘要：

  在乙腈中将 LnI3（Ln = La、Ce）或[UI3(py)4]与 3 个当量的铽处理，可得到三(铽)络合物[M(铽)3]I3。在吡啶或乙腈中向 MX3（X = I 或 OSO2CF3）中加入 3 个等量的 Rbtp（2,6-双（5,6-二烷基-1,2,4-三嗪-3-基）吡啶），可得到三（Rbtp）化合物 [M(Rbtp)3]X3。与铽离子相比，Rbtp 配体对 4f 和 5f 离子有更好的亲和力，对 U(III)的选择性比对 Ce(III) 或 La(III) 的选择性更高。1H NMR 竞争实验和 X 射线晶体学研究揭示了这一趋势，这些研究表明，在 [M(terpy)3]3+ 和 [M(Rbtp)3]3+ 阳离子中，MâN(Rbtp) 键长度比 MâN(terpy)键长度短，UâN 键长度比相应的 CeâN 或 LaâN 键距离短。

  DOI：

  10.1039/b203725d
• 作为产物：
  描述：

  2,3-丁二酮 、 pyridine-2,6-dicarbohydrazide imide 以 乙醇 为溶剂， 生成 2,6-bis-(5,6-dimethyl-[1,2,4]triazin-3-yl)-pyridine
  参考文献：
  名称：

  Trivalent Actinide and Lanthanide Complexation of 5,6-Dialkyl-2,6-bis(1,2,4-triazin-3-yl)pyridine (RBTP; R = H, Me, Et) Derivatives: A Combined Experimental and First-Principles Study

  摘要：

  Complexations of lanthanide ions with 5,6-dialkyl-2,6-bis(1,2,4-triazin-3-yl)pyridine [RBTP; R = H (HBTP), methyl (MeBTP), ethyl (EtBTP)] derivatives have been studied in the acetonitrile medium by electrospray ionization mass spectrometry, time-resolved laser-induced fluorescence spectroscopy, and UV-vis spectrophotometric titration. These studies were carried out in the absence and presence of a nitrate ion in order to understand the effect of the nitrate ion on their complexation behavior, particularly in the poor solvating acetonitrile medium where strong nitrate complexation of hard lanthanide ions is expected. Consistent results from all three techniques undoubtedly show the formation of lower stoichiometric complexes in the presence of excess nitrate ion. This kind of nitrate ion effect on the speciation of Ln(3+) complexes of RBTP ligands has not so far been reported in the literature. Different Am3+ and Ln(3+) complexes were observed with RBTP ligands in the presence of 0.01 M tetramethylammonium nitrate, and their stability constant values are determined using UV-vis spectrophotometric titrations. The formation of higher stoichiometric complexes and higher stability constants for Am3+ compared to Ln(3+) ions indicates the selectivity of these classes of ligands. A single-crystal X-ray diffraction (XRD) study of europium(III) complexes shows the formation of a dimeric complex with HBTP and a monomeric complex with EtBTP, whereas MeBTP forms both the dimeric and monomeric complexes. Density functional theory calculations confirm the findings from single-crystal XRD and also predict the structures of Eu3+ and Am3+ complexes observed experimentally.

  DOI：

  10.1021/ic301881w

文献信息

• 3-(Pyridin-2-Yl)-[1,2,4]-Triazines as Fungicides
  申请人：Grammenos Wassilios

  公开号：US20090111692A1

  公开（公告）日：2009-04-30

  The invention relates to 3-(pyridin-2-yl)-[1,2,4]-triazines of formula (I) and their use in the control of parasitic fungi and to herbicides that contain said compounds as an effective ingredient thereof. In formula (I), R 1 , R 2 independently represent OH, halogen, NO 2 , NH 2 , C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 halogenalkyl, C 1 -C 8 halogenalkoxy, C 1 -C 8 alkylamino or di(C 1 -C 8 alkyl)amino, or they form, together with the C atoms to which they are bound, a saturated five-, six- or seven-membered carbocycle or heterocycle, which, in addition to the carbon ring members, has one or two heteroatoms selected from oxygen or sulfur as the ring members, the carbocycle and the heterocycle being unsubstituted or having 1, 2, 3 or 4 C 1 -C 4 alkyl groups as the substituents; R 3 represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 halogenalkyl, C 1 -C 4 halogenalkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkylmethyl, or halogen; R 4 represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 halogenalkyl, C 1 -C 4 halogenalkoxy or halogen; R 5 represents C 1 -C 8 alkyl, C 1 -C 8 halogenalkyl, C 1 -C 8 alkoxy, C 1 -C 8 halogenalkoxy, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyloxy, five- or six-membered heteroaryl, phenyl, phenoxy, benzyl, benzyloxy, five- or six-membered heteroarylmethyl or five- or six-membered heteroaryloxy, said cyclic groups being unsubstituted or having 1, 2, 3, 4 or 5 groups R a .

  该发明涉及式(I)的3-(吡啶-2-基)-[1,2,4]-三嗪及其在控制寄生真菌方面的用途，以及含有该化合物作为有效成分的除草剂。在式(I)中，R1、R2独立地表示OH、卤素、NO2、NH2、C1-C8烷基、C1-C8烷氧基、C1-C8卤代烷基、C1-C8卤代烷氧基、C1-C8烷基氨基或二(C1-C8烷基)氨基，或它们与其结合的C原子一起形成饱和的五、六或七元碳环或杂环，除了碳环成员外，还有一个或两个氧或硫选择作为环成员的杂原子，碳环和杂环未被取代或具有1、2、3或4个C1-C4烷基基团；R3表示氢、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基、C3-C6环烷基、C3-C6环烷基甲基或卤素；R4表示氢、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基或卤素；R5表示C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C3-C8环烷基、C3-C8环烷氧基、五元或六元杂芳基、苯基、苯氧基、苄基、苄氧基、五元或六元杂芳基甲基或五元或六元杂芳氧基，所述的环基未被取代或具有1、2、3、4或5个Ra基团。
• Selective complexation of uranium(iii) over cerium(iii) by 2,6-bis(5,6-dialkyl-1,2,4-triazin-3-yl)pyridines: 1H NMR and X-ray crystallography studies
  作者：Peter B. Iveson、Christelle Rivière、Martine Nierlich、Pierre Thuéry、Michel Ephritikhine、Denis Guillaneux、Charles Madic

  DOI：10.1039/b103606h

  日期：——

  Addition of 2,6-bis(5,6-dialkyl-1,2,4-triazin-3-yl)pyridines (btp) to UI3 and CeI3 in anhydrous pyridine gave the 1∶3 complexes [M(btp)3]I3, the terdentate nitrogen ligand being completely selective for UIII over CeIII, as shown by 1H NMR competition experiments; crystal structures of analogous btp complexes of UIII and CeIII revealed that the U–N bond distances are significantly shorter than the corresponding

  将 2,6-bis(5,6-dialkyl-1,2,4-triazin-3-yl)pyridines (btp) 添加到 UI3 和 CeI3 的无水吡啶中，得到 1:3 配合物 [M(btp)3] I3，三齿氮配体对 UIII 的选择性优于 CeIII，如 1H NMR 竞争实验所示；UIII和CeIII的类似btp配合物的晶体结构表明U-N键距离明显短于相应的Ce-N距离。
• Sterically Congested Uranyl Complexes with Seven-Coordination of the UO₂ Unit: the Peculiar Ligation Mode of Nitrate in [UO₂(NO₃)₂(Rbtp)] Complexes
  作者：Jean-Claude Berthet、Pierre Thuéry、Jean-Pierre Dognon、Denis Guillaneux、Michel Ephritikhine

  DOI：10.1021/ic8004486

  日期：2008.8.4

  [Rbtp = 2,6-bis(5,6-dialkyl-1,2,4-triazin-3-yl)pyridine; R = Me, Pr ( n )] to UO 2(OTf) 2 in anhydrous acetonitrile gave the neutral compounds [UO 2(OTf) 2(Rbtp)] [R = Me ( 1), ( n )Pr ( 2)] and the cationic complexes [UO 2(Rbtp) 2][OTf] 2 [R = Me ( 3), Pr ( n ) ( 4)], respectively. No equilibrium between the mono and bis(Rbtp) complexes or between [UO 2(Rbtp) 2][OTf] 2 and free Rbtp in acetonitrile was

  加入1或2摩尔当量的Rbtp [Rbtp ＝ 2，6-双（5，6-二烷基-1,2,4-三嗪-3-基）吡啶；R = Me，Pr（n）]转化为无水乙腈中的UO 2（OTf）2得到中性化合物[UO 2（OTf）2（Rbtp）] [R = Me（1），（n）Pr（2）]和阳离子络合物[UO 2（Rbtp）2] [OTf] 2 [R = Me（3），Pr（n）（4）]。NMR谱图中未检测到单和双（Rbtp）配合物之间或乙腈中[UO 2（Rbtp）2] [OTf] 2与游离Rbtp之间的平衡。1和3的晶体结构类似于它们的三联吡啶类似物的晶体结构，而3是在不寻常的菱面体环境中与铀原子形成铀酰复合物的另一个例子。在乙腈中存在1摩尔当量的Rbtp时，UO 2（NO 3）2与[UO 2（NO 3）2（Rbtp）]处于平衡状态，未观察到双加合物的形成，即使Rbtp过多。[UO 2（NO 3）2（Rbtp）] [R
• Synthesis, structure, and redox states of homoleptic d-block metal complexes with bis-1,2,4-triazin-3-yl-pyridine and 1,2,4-triazin-3-yl-bipyridine extractants
  作者：Michael G.B. Drew、Mark R.St.J. Foreman、Andreas Geist、Michael J. Hudson、Frank Marken、Virginia Norman、Michael Weigl

  DOI：10.1016/j.poly.2005.09.030

  日期：2006.3

  it has been established that triazinyl bipyridines (hemi-BTPs) and bis-triazinyl pyridines (BTPs), ligands which are currently being investigated as possible ligands for the separation of actinides from lanthanides in nuclear waste, are able to form homoleptic complexes with first row transition metals such as cobalt(IT), copper(II), iron(II), manganese(II), nickel(II) and zinc(II). The metal complexes exhibit six-co-ordinate octahedral structures and redox states largely analogous to those of the related terpyridine complexes. The reactivity of the different redox states of cobalt bis-hemi-BTP complex in aqueous environments has been studied with two-phase electrochemistry by immobilisation of the essentially water-insoluble metal complexes on graphite electrodes and the immersion of this modified electrode in an aqueous electrolyte.It was found that redox potentials for the metal-centred reactions were pH-independent whereas the potentials for the ligand-centred reactions were strongly pH-dependent. The reductive degradation of these complexes has been investigated by computational methods. Solvent extraction experiments have been carried out for a range of metals and these show that cobalt(II) and nickel(II) as well as palladium(II), cadmium(II) and lead(II) were all extracted with the ligands 1e and 2c with higher distribution ratios that was observed for americium(III) under the same conditions. The implications of this result for the use of these ligands to separate actinides from nuclear waste are discussed. (c) 2005 Elsevier Ltd. All rights reserved.
• 3-(PYRIDIN-2-YL)-[1,2,4]-TRIAZINE ALS FUNGIZIDE
  申请人：BASF SE

  公开号：EP2010514B1

  公开（公告）日：2010-12-29