2,6-di[4-(hydroxymethyl)pyrazol-1-yl]pyridine | 1192035-41-8

• 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-di[4-(hydroxymethyl)pyrazol-1-yl]pyridine
• 英文别名: [1-[6-[4-(Hydroxymethyl)pyrazol-1-yl]pyridin-2-yl]pyrazol-4-yl]methanol；[1-[6-[4-(hydroxymethyl)pyrazol-1-yl]pyridin-2-yl]pyrazol-4-yl]methanol
• CAS: 1192035-41-8
• 化学式: C₁₃H₁₃N₅O₂
• 分子量: 271.279
• InChiKey: QQDJGIMZCMNEAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  89
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  iron(II) tetrafluoroborate hexahydrate 、 2,6-di[4-(hydroxymethyl)pyrazol-1-yl]pyridine 、 水 以 丙酮 为溶剂， 以53%的产率得到bis(2,6-di[4-(hydroxymethyl)pyrazol-1-yl]pyridine)iron(II) tetrafluoroborate monohydrate
  参考文献：
  名称：

  Two new 4′,4′′-disubstituted dipyrazolylpyridine derivatives, and the structures and spin states of their iron(II) complexes

  摘要：

  Reaction of 2 equiv of the sodium salt of ethyl pyrazole-4-carboxylate, with 1 equiv of 2,6-dibromopyridine, in diglyme at 130 degrees C for 5 days yields 2,6-di[4-(ethylcarboxy)pyrazol-1-yl] pyridine (L-1), with 2-bromo-6-[4-(ethylcarboxy)pyrazol-1-yl] pyridine (L-2) as a signi. cant byproduct. Reduction of L-1 with excess NaBH4 in thf affords 2,6-di[4-(hydroxymethyl)pyrazol-1-yl] pyridine (L-3) in low yield. The crystalline complex [Fe(L-1)(2)][BF4](2)center dot 2CF(3)CH(2)OH is low-spin at 150 K, while bulk samples with this formula are approximately 10% high-spin and 90% low-spin at room temperature. This ratio does not vary significantly on cooling from its magnetic susceptibility, suggesting that the material might be contaminated by a second, minor high-spin phase. Single crystals of [Fe(L-3)(2)][BF4](2)center dot 1.4CH(3)CN have a mixed spin-state population, with the low-spin state predominating at 150 K. The [Fe(L-3)(2)(BF4)](+) moieties in the lattice associate into 1-D chains through intermolecular O-H center dot center dot center dot O and O-H center dot center dot center dot F hydrogen bonding. Bulk samples of [Fe(L-3)(2)][BF4](2)center dot H2O are fully low-spin below 200 K, but the magnetic data imply the onset of a gradual thermal spin-transition centred above room temperature. DSC and TGA measurements imply that this transition is centred at 322 K, and involves loss of lattice water. Both complexes undergo spin-crossover in (CD3)(2)CO solution, with transition midpoints near 250 K. (C) 2009 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2009.01.022

文献信息

• Two new 4′,4′′-disubstituted dipyrazolylpyridine derivatives, and the structures and spin states of their iron(II) complexes
  作者：Ruth Pritchard、Colin A. Kilner、Simon A. Barrett、Malcolm A. Halcrow

  DOI：10.1016/j.ica.2009.01.022

  日期：2009.9

  Reaction of 2 equiv of the sodium salt of ethyl pyrazole-4-carboxylate, with 1 equiv of 2,6-dibromopyridine, in diglyme at 130 degrees C for 5 days yields 2,6-di[4-(ethylcarboxy)pyrazol-1-yl] pyridine (L-1), with 2-bromo-6-[4-(ethylcarboxy)pyrazol-1-yl] pyridine (L-2) as a signi. cant byproduct. Reduction of L-1 with excess NaBH4 in thf affords 2,6-di[4-(hydroxymethyl)pyrazol-1-yl] pyridine (L-3) in low yield. The crystalline complex [Fe(L-1)(2)][BF4](2)center dot 2CF(3)CH(2)OH is low-spin at 150 K, while bulk samples with this formula are approximately 10% high-spin and 90% low-spin at room temperature. This ratio does not vary significantly on cooling from its magnetic susceptibility, suggesting that the material might be contaminated by a second, minor high-spin phase. Single crystals of [Fe(L-3)(2)][BF4](2)center dot 1.4CH(3)CN have a mixed spin-state population, with the low-spin state predominating at 150 K. The [Fe(L-3)(2)(BF4)](+) moieties in the lattice associate into 1-D chains through intermolecular O-H center dot center dot center dot O and O-H center dot center dot center dot F hydrogen bonding. Bulk samples of [Fe(L-3)(2)][BF4](2)center dot H2O are fully low-spin below 200 K, but the magnetic data imply the onset of a gradual thermal spin-transition centred above room temperature. DSC and TGA measurements imply that this transition is centred at 322 K, and involves loss of lattice water. Both complexes undergo spin-crossover in (CD3)(2)CO solution, with transition midpoints near 250 K. (C) 2009 Elsevier B. V. All rights reserved.