5,6-diphenyl-3-(pyrazin-2-yl)-1,2,4-triazine | 18091-47-9

• 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: 5,6-diphenyl-3-(pyrazin-2-yl)-1,2,4-triazine
• 英文别名: 5,6-diphenyl-3-(2-pyrazinyl)-1,2,4-triazine；3-(pyrazin-2-yl)-5,6-diphenyl-as-triazine；5,6-diphenyl-3-pyrazin-2-yl-[1,2,4]triazine；pyrazinyltriazine；3-Pyrazyl-5,6-diphenyl-asymm.-triazin；5,6-diphenyl-3-pyrazin-2-yl-1,2,4-triazine
• CAS: 18091-47-9
• 化学式: C₁₉H₁₃N₅
• 分子量: 311.346
• InChiKey: JWAXAEHWBBUTFR-UHFFFAOYSA-N

物化性质

• 沸点：
  534.5±60.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  64.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 5,6-diphenyl-3-(pyrazin-2-yl)-1,2,4-triazine 以 苯 为溶剂， 以80%的产率得到fac-[Re(I) (CO)3 (5,6-diphenyl-3-(pyrazin-2-yl)-1,2,4-triazine) (chloride)]
  参考文献：
  名称：

  Synthesis and structure of luminescent ReI(CO)3Cl complexes incorporating pyridyltriazine, pyrazinyltriazine and triazolopyridine chelation

  摘要：

  The triazine and triazolo ligands (general abbreviations, L) used in the present work are pyridyltriazine (L-1), pyrazinyltriazine (L-2) and triazolopyridine (L-3), respectively. The reaction of Re(CO)(5)Cl with a slight excess of L in boiling benzene has furnished complexes of the type Re(CO)(3)Cl(L). In dichloromethane solution the complexes display a band of moderate intensity in the visible region: Re-I (CO)(3)Cl(L-1), 433 nm; Re-I(CO)(3)Cl(L-2) 451 nm and Re-I(CO)(3)(L-3) 440 nm. This band is tentatively assigned to a pi(Re) --> pi*(L) MLCT excitation. The solutions are also fluorescent, the emission peaks lying at 679, 671 and 592 nm, respectively. The fluorescence is believed to originate from the (MLCT)-M-3 state. The quantum yield in the three cases are 5.6 x 10(-4), 5.5 x 10(-4) and 0.036, respectively. Interestingly the L 3 complex is comparable with Ru(bpy)(3)(2+) with regard to quantum yield. The IR and H-1 NMR spectra of the chelates are reported. The complexes are electroactive in acetonitrile solution wherein an irreversible one-electron anodic oxidation (1.30-1.50 V) is observed cyclic voltammetrically. The X-ray structures of the L-1 and L-3 complexes have been determined revealing distorted octahedral ReC3N2Cl coordination spheres. The carbon monoxide ligands are facially disposed. In both complexes the chelate rings make a satisfactory plane (mean deviation 0.03 angstrom). The average Re-N, Re-C and Re-Cl lengths are unexceptional. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2006.01.028

文献信息

• Oxidorhenium( <scp>V</scp> ) Complexes of a Family of Bipyridine‐Like Ligands Including Pyridyltriazines and Pyrazinyltriazine: Oxygen‐Atom Transfer, Metal Redox and Correlations
  作者：Samir Das、Animesh Chakravorty

  DOI：10.1002/ejic.200501102

  日期：2006.6

  derivatives, phenanthroline (phen), 5,6-diphenyl-3-(2-pyridyl)-1,2,4-triazine (ppyt) and its dimethyl (mpyt) and pyrazinyl (ppzt) analogues. The concerned oxido complexes are [ReOCl3(L)],[ReOBr3(ppyt)] and [ReOBr3(ppzt)]. The chloro and bromo complexes of ppyt and ppzt were prepared by reacting these ligands with [ReOX3(AsPh3)2] (X = Cl, Br). The X-ray structures of [ReOCl3(ppyt)] and [ReOCl3(ppzt)] reveal

  标题配体（通用缩写L）为联吡啶（bpy）、其二甲基（mbpy）和二苯基（pbpy）衍生物、菲咯啉（phen）、5,6-二苯基-3-（2-吡啶基）-1,2,4 -三嗪 (ppyt) 及其二甲基 (mpyt) 和吡嗪基 (ppzt) 类似物。相关的氧化配合物是[ReOCl3(L)]、[ReOBr3(ppyt)]和[ReOBr3(ppzt)]。ppyt 和 ppzt 的氯和溴配合物是通过这些配体与 [ReOX3(AsPh3)2] (X = Cl, Br) 反应制备的。[ReOCl3(ppyt)] 和 [ReOCl3(ppzt)] 的 X 射线结构表明 ReCl3 片段是经向排列的，L 配体是 N,N 配位的，因此吡啶/吡嗪氮与氧化氧原子。Re-O 长度 [1.656(10)/1.625(9) A] 对应于近似的三键。氧原子从溶液中的 [ReOX3(L)] 转移到三苯基膦的速率遵循二级动力学，并与大的负活化熵（约
• Ruthenium(ii) complexes containing asymmetric ligands: synthesis, characterization, crystal structure and DNA-binding
  作者：Hong Deng、Jiwen Cai、Hong Xu、Hao Zhang、Liang-Nian Ji

  DOI：10.1039/b208400g

  日期：2003.1.29

  Two new asymmetric ligands, 3-(pyrazin-2-yl)-as-triazino[5,6-f]acenaphthylene (dta) and 3-(pyrazin-2-yl)-as-triazino[5,6-f]phenanthrene (dpt) and three novel ruthenium(II) complexes [Ru(bpy)2(L)][ClO4]2 (bpy = 2,2′-bipyridine, L = ddt (1), dta (2) and dpt (3), ddt = 3-(pyrazin-2-yl)-5,6-diphenyl-as-triazine) have been synthesized and characterized by mass spectroscopy, 1H NMR and cyclic voltammetry. The crystal structures of dta and [Ru(bpy)2(ddt)][ClO4]2 (1) were also determined. Interactions of the complexes with calf thymus DNA have also been investigated by spectrophotometric and viscosity measurements. The planar extension of the intercalative ligand increases the interaction of the complex with DNA, indicating that the size and shape of the intercalated ligand have a marked effect on the strength of interaction. The circular dichroism signals of the dialysates of the racemic complexes against calf thymus DNA suggest that complexes 2 and 3 interact enantioselectively with calf thymus DNA, but not complex 1. Complexes 2 and 3 have been found to promote the cleavage of plasmid pBR 322 DNA from the supercoiled form I to the open circular form II upon irradiation.

  两种新的不对称配体，3-(吡嗪-2-基)-类三嗪并[5,6-f]苊烯（dta）和 3-(吡嗪-2-基)-类三嗪并[5,6-f]菲（dpt）以及三种新的钌(II)配合物[Ru(bpy)2(L)][ClO4]2（bpy = 2、2′-联吡啶，L = ddt (1)、dta (2) 和 dpt (3)，ddt = 3-（吡嗪-2-基）-5,6-二苯基异三嗪）的合成，并通过质谱、1H NMR 和循环伏安法对其进行了表征。还测定了 dta 和 [Ru(bpy)2(ddt)][ClO4]2 (1) 的晶体结构。还通过分光光度法和粘度测量法研究了复合物与小牛胸腺 DNA 的相互作用。插层配体的平面延伸增加了配合物与 DNA 的相互作用，表明插层配体的大小和形状对相互作用的强度有明显的影响。外消旋络合物透析液对小牛胸腺 DNA 的圆二色性信号表明，络合物 2 和 3 与小牛胸腺 DNA 有对映选择性的相互作用，而络合物 1 则没有。研究发现，络合物 2 和 3 能促进质粒 pBR 322 DNA 在辐照下从超卷曲形式 I 分裂成开放的环状形式 II。
• Synthesis and characterization of new imidorhenium(V) and imidorhenium(VI) complexes of pyridyltriazines and pyrazinyltriazine with halide coligands including rare iodide
  作者：Samir Das

  DOI：10.1016/j.ica.2008.02.001

  日期：2008.6

  The blue colored imido complexes [Re(NC6H4Cl)X-3(L)] have been synthesized by three methods: (i) reaction of [(ReOX3)-O-V(L)] with p-ClC6H4NH2, (ii) reaction of [Re-III(OPPh3)X-3(L)] with p-ClC6H4NH2 and (iii) reaction of [(ReOX3)-O-V(PPh3)(2)] with L followed by the addition of p-ClC6H4NH2 in boiling toluene. Here, X = Cl, Br, I and L are 5,6-diphenyl-3-(2-pyridyl)-1,2,4-triazine (L-2) and its dimethyl (L-1) and pyrazinyl (L-3) analogues. The [Re(NC6H4Cl) Cl-3(L-1)] (1a), [Re(NC6H4Cl)Cl-3(L-2)] (1b), [Re(NC6H4Cl) Br-3(L-2)] (1c), [Re(NC6H4Cl)I-3(L-2)] (1d), [Re(NC6H4Cl)Cl-3(L-3)] (1e), [Re(NC6H4Cl)Br-3(L-3)] (1f), [Re(NC6H4Cl)I-3(L-3)] (1g), complexes have been characterized electrochemically and spectroscopically. The X-ray structures of [Re(NC6H4Cl)Cl-3(L-2)] and [Re(NC6H4Cl)I-3(L-3)] reveal that the ReCl3 fragment is meridionally disposed and that the L ligand is N,N-coordinated such that the pyridine/pyrazine nitrogen lies trans to the imide nitrogen. The feasibility of generating the rhenium(VI) congener of the imidorhenium(V) complex is also examined with the help of six-line EPR spectra at room temperature. (c) 2008 Elsevier B.V. All rights reserved.
• Synthesis and structure of luminescent ReI(CO)3Cl complexes incorporating pyridyltriazine, pyrazinyltriazine and triazolopyridine chelation
  作者：Samir Das、Bikash Kumar Panda

  DOI：10.1016/j.poly.2006.01.028

  日期：2006.7

  The triazine and triazolo ligands (general abbreviations, L) used in the present work are pyridyltriazine (L-1), pyrazinyltriazine (L-2) and triazolopyridine (L-3), respectively. The reaction of Re(CO)(5)Cl with a slight excess of L in boiling benzene has furnished complexes of the type Re(CO)(3)Cl(L). In dichloromethane solution the complexes display a band of moderate intensity in the visible region: Re-I (CO)(3)Cl(L-1), 433 nm; Re-I(CO)(3)Cl(L-2) 451 nm and Re-I(CO)(3)(L-3) 440 nm. This band is tentatively assigned to a pi(Re) --> pi*(L) MLCT excitation. The solutions are also fluorescent, the emission peaks lying at 679, 671 and 592 nm, respectively. The fluorescence is believed to originate from the (MLCT)-M-3 state. The quantum yield in the three cases are 5.6 x 10(-4), 5.5 x 10(-4) and 0.036, respectively. Interestingly the L 3 complex is comparable with Ru(bpy)(3)(2+) with regard to quantum yield. The IR and H-1 NMR spectra of the chelates are reported. The complexes are electroactive in acetonitrile solution wherein an irreversible one-electron anodic oxidation (1.30-1.50 V) is observed cyclic voltammetrically. The X-ray structures of the L-1 and L-3 complexes have been determined revealing distorted octahedral ReC3N2Cl coordination spheres. The carbon monoxide ligands are facially disposed. In both complexes the chelate rings make a satisfactory plane (mean deviation 0.03 angstrom). The average Re-N, Re-C and Re-Cl lengths are unexceptional. (C) 2006 Elsevier Ltd. All rights reserved.