2,6-bis(3,4,5-trimethyl-N-pyrazolyl)pyridine | 849700-65-8

• 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: 2,6-bis(3,4,5-trimethyl-N-pyrazolyl)pyridine
• 英文别名: 2,6-bis(3,4,5-trimethylpyrazolyl)pyridine；btmpp；2,6-bis(3,4,5-trimethylpyrazol-1-yl)pyridine
• CAS: 849700-65-8
• 化学式: C₁₇H₂₁N₅
• 分子量: 295.387
• InChiKey: YTSYMJMRLRZFQI-UHFFFAOYSA-N

物化性质

• 熔点：
  114 °C
• 沸点：
  491.0±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  48.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-bis(3,4,5-trimethyl-N-pyrazolyl)pyridine 、 mercury(II) thiocyanate 以 乙醇 为溶剂， 以67%的产率得到Hg(2,6-bis(3,4,5-trimethyl-N-pyrazolyl)pyridine)(SCN)2
  参考文献：
  名称：

  基于吡唑的 NNN 型配体的锌 (II) 和汞 (II) 配合物：合成、X 射线结构、热分析和 DFT 研究

  摘要：

  合成了含有三足氮供体配体 2,6-双（3,4,5-三甲基-N-吡唑基）吡啶（btmpp）的单体锌（II）和汞（II）配合物，并通过元素和光谱（IR， UV/Vis) 分析、TG-DTA 和单晶 X 射线衍射研究。复合物 [Zn(btmpp)Cl2] (2) 和 [Hg(btmpp)(SCN)2] (3) 的 X 射线分析表明，这两种结构都在空间群 P21/c 中结晶，a = 7.9722(6)， b = 18.3084(13), c = 13.3117(9) A and Z = 4 for 2 and a = 8.7830(3), b = 21.1489(7), c = 12.0682(4) A and Z = 4 for 3。单体单元包含扭曲的方形锥体排列的五配位金属离子。配合物 2 和 3 的结构也在 B3LYP/LanL2DZ 水平用 DFT 方法计算，并且与从 X 射线分析获得的实验值非常一致。还报告了

  DOI：

  10.1002/zaac.201100077
• 作为产物：
  描述：

  2,6-二氯吡啶 、 sodium salt of 3,4,5-trimethylpyrazole 以 二乙二醇二甲醚 为溶剂， 反应 120.0h， 生成 2,6-bis(3,4,5-trimethyl-N-pyrazolyl)pyridine
  参考文献：
  名称：

  作为群体感应抑制剂的新型混合配体 Co(II) 复合物的合成、结构表征和生物学评价

  摘要：

  摘要 抗生素耐药性是二十一世纪最大的健康问题之一。为了应对这一全球性问题，需要替代预防策略，例如群体感应中断。因此，开发具有抗群体感应活性的新化合物非常重要。在这里，我们介绍了两种新的 Co (II) 配合物的合成和结构表征；[Co(btmpp)(NCO)2], 1 和 [Co(btmpp)(NCSe)2], 2（其中 btmpp 是：2,6-双（3,4,5-三甲基吡唑基）吡啶）。使用单晶 X 射线衍射确定这两种配合物的晶体结构。Co(II) 原子的配位环境可以描述为扭曲的四角锥几何形状。筛选了两种复合物对革兰氏阳性菌（枯草芽孢杆菌）和革兰氏阴性菌（铜绿假单胞菌、鼠伤寒沙门氏菌、沙门氏菌）的抗菌活性。Sonnei, Y. enterocolitica) 细菌菌株。还检查了这些复合物对细菌的 QS 调节行为的影响，如集群和生物膜形成。发现所有细菌对复合物 2 比复合物 1 更敏感。

  DOI：

  10.1016/j.molstruc.2019.127322

文献信息

• Synthesis, characterization and thermal properties of cobalt(II), nickel(II) and copper(II) complexes of 2,6-bis(3,4,5-trimethyl-N-pyrazolyl)pyridine): the crystal structure of [Co(btmpp)(H2O)2(NO3)]NO3
  作者：Çiğdem Hopa、Raif Kurtaran、Mahir Alkan、Hulya Kara、Robert Hughes

  DOI：10.1007/s11243-010-9424-4

  日期：2010.11

  Co(II), Ni(II) and Cu(II) nitrate complexes with btmpp, namely ([Co(btmpp)(H2O)2(NO3)]NO3 (1), [Ni(btmpp)(H2O)(NO3)]NO3 (2) and [Cu(btmpp)(MeOH)(NO3)]NO3 (3), where btmpp = 2,6-bis(3,4,5-trimethyl-N-pyrazolyl)pyridine), have been synthesized and characterized by physicochemical and spectroscopic methods. The crystal structure of complex 1 has been determined by single crystal diffraction at 100K. In

  Co(II)、Ni(II)和Cu(II)硝酸盐与btmpp复合，即([Co(btmpp)(H2O)2(NO3)] (1)、[Ni(btmpp)( )( ) ] (2) 和 [Cu(btmpp)(MeOH)( )] (3)，其中 btmpp = 2,6-双（3,4,5-三甲基-N-吡唑基）吡啶）已合成并通过物理化学和光谱方法表征。配合物 1 的晶体结构已通过 100K 的单晶衍射确定。在所有配合物中，btmpp 通过其氮原子以三齿模式配位。配合物 1 中的一个硝酸盐通过氧原子与金属中心末端键合，而另一个在配位球外。配合物 1 中的 Co(II) 原子与 CoN3O3 扭曲的八面体环境六配位。用热重分析法分析了三种配合物的分解。
• Synthesis, characterization and anti-proliferative activity of Cd(II) complexes with NNN type pyrazole-based ligand and pseudohalide ligands as coligand
  作者：Cigdem Hopa、Hatice Yildirim、Hulya Kara、Raif Kurtaran、Mahir Alkan

  DOI：10.1016/j.saa.2013.10.028

  日期：2014.3

  Cd(II) complexes of tridentate nitrogen donor ligand, 2,6-bis(3,4,5-trimethylpyrazolyl)pyridine (btmpp), Cd(btmpp)X2 (X:Cl, ONO or N(CN)2) have been synthesized and characterized by elemental and spectral (FT-IR, 1H NMR, 13C NMR, UV–Vis) analyses, differential thermal analysis and single crystal X-ray diffraction studies. The molecular structure of reported complex 1, revealed distorted square-pyramidal

  三齿氮供体配体，2,6-双（3,4,5-三甲基吡唑基）吡啶（btmpp），Cd（btmpp）X 2（X：Cl，ONO或N（CN）2）的Cd（II）配合物具有通过元素和光谱（FT-IR，1 H NMR，13 C NMR，UV-Vis）分析，差热分析和单晶X射线衍射研究对其进行了合成和表征。报道的配合物1的分子结构揭示了镉周围方形棱锥几何形状的扭曲。配合1 - 3测试了相应的配体和相应的配体对人癌细胞系HEP3B（肝细胞癌），PC3（前列腺腺癌），MCF7（乳腺腺癌）和Saos2（骨肉瘤）的细胞毒活性。结果表明，复合物比游离配体更具细胞毒性，复合物2是PC3最具细胞毒性的复合物。
• Chloro-Bridged Dimeric Cadmium(II)-Isothiocyanate Complex with a Tridentate NNN Type Ligand: Synthesis, X-ray Structure, Thermal Analysis
  作者：Çiğdem Hopa、Mahir Alkan、Canan Kazak、N. Burcu Arslan、Raif Kurtaran

  DOI：10.1007/s10870-009-9625-x

  日期：2010.2

  The dinuclear cadmium(II) complex with 2,6-bis(3,4,5-trimethyl-N-pyrazolyl)pyridine (btmpp) has been synthesized, and characterized by single crystal X-ray diffraction, IR, UV–Vis and TGA–DTA methods. Cd atoms are located in a distorted octahedral environment in the complex. The complex crystalizes in monoclinic space group C 2/c, with unit cell dimensions a = 20.5636(12) Å, b = 14.0167(13) Å, c = 15.6598(11) Å, β = 113.425(5)o, V = 4141.7(5) Å3. There are two intermolecular and a intramolecular hydrogen bonds interactions in crystal. A new chloro-bridged Cd(II)-isothiocyanato complex with NNN type ligand synthesized and characterized by FT-IR, UV–Vis, single crystal X-ray and thermal analysis.

  研究人员合成了 2,6-双（3,4,5-三甲基-N-吡唑基）吡啶（btmpp）的双核镉（II）配合物，并通过单晶 X 射线衍射、红外光谱、紫外可见光谱和 TGA-DTA 方法对其进行了表征。络合物中的镉原子位于扭曲的八面体环境中。该复合物晶体为单斜空间群 C 2/c，单胞尺寸 a = 20.5636(12) Å, b = 14.0167(13) Å, c = 15.6598(11) Å, β = 113.425(5)o, V = 4141.7(5) Å3.晶体中有两个分子间氢键和一个分子内氢键相互作用。通过傅立叶变换红外光谱、紫外可见光谱、单晶 X 射线和热分析，合成了一种新的氯桥镉(II)-异硫氰配合物。
• Nitrito complexes of nickel(II), copper(II) and cobalt(II) with tridentate pyrazole based planer ligand: Structure, spectroscopy, thermal properties and imitative nuclease activity
  作者：Cigdem Hopa、Raif Kurtaran、Ersin Hopa、Gulcin Cetin、Ekrem Dundar、Hulya Kara、Mahir Alkan

  DOI：10.1016/j.ica.2014.12.035

  日期：2015.4

  Functional documentation of metal complexes are essential for various aspects including gene function/regulation and drug design for lethal diseases like cancer (Sigel and Martin (1982), Peters et al. (1997), Martin and Mascharak (2000), Hazra et al. (2007), Zhang et al. (2002), Patra et al. (2003)). Therefore, we have synthesized three new nitrite bound coordination complexes with the ligand 2,6-bis (3,4,5-trimethylpyrazole) pyridine (btmpp), [Ni(btmpp)(ONO)(2)] (1), [Cu(btmpp)(ONO)(2)] (2) and [Co(btmpp)(ONO)(2)] (3) and complexes were characterized by elemental analysis, IR spectroscopy and X-ray single-crystal diffraction analysis. Thermal stabilities of these complexes were studied by thermogravimetric (TG) and differential thermal analyses (DTA). The single crystal X-ray analyses showed that the geometry around the Ni atom was distorted octahedral with NiN3O3 coordination sphere. One of the nitrites in complex 1 is terminally bonded to the metal centre through the oxygen atom, whereas the other one is chelated as a bidentate through both oxygen atoms. In complex 2, the coordination around the Cu atom is a distorted square-pyramid (tau = 0.083) involving three N atoms from btmpp and two oxygen atoms from nitrites. Both nitrite groups are terminally bonded to the metal. DNA interaction properties of the compounds were also analyzed by agarose gel electrophoresis. The results indicated that all of the complexes converted supercoiled plasmid DNA (pET21a) into its nicked-circular form without addition of any external agents at physiological conditions. Complex 2 was the most effective on the cleavage of DNA, and its activity was observed as a conversion of double stranded DNA into nicked and linear form. (C) 2015 Elsevier B.V. All rights reserved.