4-(1H-pyrazol-1-yl)-2-(pyridin-2-yl)-6-methylpyrimidine | 1428770-00-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(1H-pyrazol-1-yl)-2-(pyridin-2-yl)-6-methylpyrimidine
• 英文别名: 2-(pyridin-2-yl)-4-(1H-pyrazol-1-yl)-6-methylpyrimidine；4-Methyl-6-pyrazol-1-yl-2-pyridin-2-ylpyrimidine；4-methyl-6-pyrazol-1-yl-2-pyridin-2-ylpyrimidine
• CAS: 1428770-00-6
• 化学式: C₁₃H₁₁N₅
• 分子量: 237.264
• InChiKey: SRMOKRZKNWTDDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  copper(II) choride dihydrate 、 4-(1H-pyrazol-1-yl)-2-(pyridin-2-yl)-6-methylpyrimidine 以 乙醇 为溶剂， 以71%的产率得到[Cu(4-methyl-6-(1H-pyrazol-1-yl)-2-(pyridin-2-yl)pyrimidine)Cl₂]·0.5H₂O
  参考文献：
  名称：

  Mono-, di-, tetra- and heptanuclear copper(II) complexes with 4-(3,5-di-R-1H-pyrazol-1-yl)-6-methyl-2-(pyridin-2-yl)pyrimidines (R=H, Me): Syntheses, crystal structures and electrospray ionization mass spectrometry

  摘要：

  A series of mono- and oligonuclear copper(II) complexes with new hybrid NNN-tridentate 4-(1H-pyrazol-1-yl)-2-(pyridin-2-yl)pyrimidine ligands, 4-(1H-pyrazol-1-yl)-2-(pyridin-2-yl)-6-methylpyrimidine (L-1) and 4-(3,5-dimethyl-1H-pyrazol-1-yl)-2-(pyridin-2-yl)-6-methylpyrimidine (L-2), have been synthesized. The reaction of CuCl2 with L-1 in EtOH in the 1: 1 metal-to-ligand molar ratio affords the mononuclear complex [(CuLCl2)-Cl-1]center dot 0.5H(2)O (1). An increase of the metal-to-ligand molar ratio up to 4: 1 as well as the use of less polar mixed solvent, EtOH/CHCl3, leads to mononuclear complex [(CuLCl2)-Cl-1] (2). Attempts to crystallize di- or oligonuclear copper(II) complex with L-1 (the 8:1 metal-to-ligand molar ratio, EtOH/CHCl3) resulted in the formation of ionic halocuprate compound, [(CuL14Cl12)-L-7][Cu2Cl6] (3), containing unique heptanuclear cation, [(CuL4Cl12)-L-7-Cl-1](2+), and dinuclear anion [Cu2Cl6](2) . The reaction of CuCl2 with L-2 in EtOH in the 1:1 metal-to-ligand molar ratio affords mononuclear complex [CuL2Cl2] (4). Di- and tetranuclear complexes, [Cu2L2Cl4] (5) and [(Cu4L2Cl8)-Cl-2] (6), can be crystallized from ethanolic solution when the 2: 1 metal-to-ligand molar ratio is used. The former is the product of kinetic control, while the latter is that of thermodynamic one. Being coordinated, the molecules of L-1 and L-2 adopt tridentate chelating coordination mode binding copper atoms through pyrazolyl N-2, pyrimidine N-3 and pyridinyl N atoms and forming thus two five-membered chelate rings (CuN3C and CuN2C2). Depending on the metal-to-ligand molar ratio in the solution, electrospray ionization mass spectrometry (ESI-MS) evidenced the presence of mono- and oligonuclear copper species in the CuCl2-L-1 and CuCl2-L-2 solutions. The isolation of oligonuclear species in the solid state seems to be related with the absence of hydrogen-bond donor groups in the molecules of 4-(1H-pyrazol-1-yl)-2-(pyridin-2-yl) pyrimidine ligands. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.10.018
• 作为产物：
  描述：

  1,1,3,3-四甲氧基丙烷 、 4-hydrazinyl-6-methyl-2-(pyridin-2-yl)pyrimidine 在 盐酸 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 1.0h， 以75%的产率得到4-(1H-pyrazol-1-yl)-2-(pyridin-2-yl)-6-methylpyrimidine
  参考文献：
  名称：

  Mono-, di-, tetra- and heptanuclear copper(II) complexes with 4-(3,5-di-R-1H-pyrazol-1-yl)-6-methyl-2-(pyridin-2-yl)pyrimidines (R=H, Me): Syntheses, crystal structures and electrospray ionization mass spectrometry

  摘要：

  A series of mono- and oligonuclear copper(II) complexes with new hybrid NNN-tridentate 4-(1H-pyrazol-1-yl)-2-(pyridin-2-yl)pyrimidine ligands, 4-(1H-pyrazol-1-yl)-2-(pyridin-2-yl)-6-methylpyrimidine (L-1) and 4-(3,5-dimethyl-1H-pyrazol-1-yl)-2-(pyridin-2-yl)-6-methylpyrimidine (L-2), have been synthesized. The reaction of CuCl2 with L-1 in EtOH in the 1: 1 metal-to-ligand molar ratio affords the mononuclear complex [(CuLCl2)-Cl-1]center dot 0.5H(2)O (1). An increase of the metal-to-ligand molar ratio up to 4: 1 as well as the use of less polar mixed solvent, EtOH/CHCl3, leads to mononuclear complex [(CuLCl2)-Cl-1] (2). Attempts to crystallize di- or oligonuclear copper(II) complex with L-1 (the 8:1 metal-to-ligand molar ratio, EtOH/CHCl3) resulted in the formation of ionic halocuprate compound, [(CuL14Cl12)-L-7][Cu2Cl6] (3), containing unique heptanuclear cation, [(CuL4Cl12)-L-7-Cl-1](2+), and dinuclear anion [Cu2Cl6](2) . The reaction of CuCl2 with L-2 in EtOH in the 1:1 metal-to-ligand molar ratio affords mononuclear complex [CuL2Cl2] (4). Di- and tetranuclear complexes, [Cu2L2Cl4] (5) and [(Cu4L2Cl8)-Cl-2] (6), can be crystallized from ethanolic solution when the 2: 1 metal-to-ligand molar ratio is used. The former is the product of kinetic control, while the latter is that of thermodynamic one. Being coordinated, the molecules of L-1 and L-2 adopt tridentate chelating coordination mode binding copper atoms through pyrazolyl N-2, pyrimidine N-3 and pyridinyl N atoms and forming thus two five-membered chelate rings (CuN3C and CuN2C2). Depending on the metal-to-ligand molar ratio in the solution, electrospray ionization mass spectrometry (ESI-MS) evidenced the presence of mono- and oligonuclear copper species in the CuCl2-L-1 and CuCl2-L-2 solutions. The isolation of oligonuclear species in the solid state seems to be related with the absence of hydrogen-bond donor groups in the molecules of 4-(1H-pyrazol-1-yl)-2-(pyridin-2-yl) pyrimidine ligands. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.10.018

文献信息

• Spin crossover in iron(II) hexafluorophosphate complexes with 2-(pyridin-2-yl)-4-(3,5-di-R-1H-pyrazol-1-yl)-6-methylpyrimidines
  作者：Mark B. Bushuev、Katerina A. Vinogradova、Yuri V. Gatilov、Ilya V. Korolkov、Elena B. Nikolaenkova、Viktor P. Krivopalov

  DOI：10.1016/j.ica.2017.08.006

  日期：2017.10

  bonds. In the stricture of [FeL(Me,Me)2](PF6)2·nH2O the cations and anions are assembled into a 3D network via CH…F hydrogen bonds and lone pair…π interactions. Both complexes demonstrate high thermal stability. Under vacuum, the complex [FeL(Me,Me)2](PF6)2·nH2O is predominantly in the low spin state below 400 K, but at higher temperatures it shows gradual spin state switching which remains incomplete

  具有N，N，N-三齿配体，2-（吡啶-2-基）-4-（1H-吡唑-1-基）-6-甲基嘧啶（L（H，H））的六氟磷酸铁（II）配合物通过使FeCl2·4H2O（NBu4）反应合成2-（吡啶-2-基）-4-（3,5-二甲基-1H-吡唑-1-基）-6-甲基嘧啶（L（Me，Me）） PF6和L（H，H）或L（Me，Me）在酒精介质中。[FeL（H，H）2]（PF6）2·nH2O的超分子3D结构由CH…π相互作用，π…π堆积和CH…F氢键组成。在[FeL（Me，Me）2]（PF6）2·nH2O的约束下，阳离子和阴离子通过CH…F氢键和孤对…π相互作用组装成3D网络。两种配合物均显示出高的热稳定性。在真空下，复合物[FeL（Me，Me）2]（PF6）2·nH2O主要处于低于400 K的低自旋状态，但在较高温度下，它显示出逐渐的自旋状态转换，即使在495 K时也保持不完全。在真空中或在第一次加热运行的密