2,2',2"-[methylidynetri(1H-pyrazol-1,3-diyl)]tris[6-bromopyridine] | 603128-46-7

• 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: 2,2',2"-[methylidynetri(1H-pyrazol-1,3-diyl)]tris[6-bromopyridine]
• 英文别名: 2-[1-[Bis[3-(6-bromopyridin-2-yl)pyrazol-1-yl]methyl]pyrazol-3-yl]-6-bromopyridine
• CAS: 603128-46-7
• 化学式: C₂₅H₁₆Br₃N₉
• 分子量: 682.174
• InChiKey: RDGUJWLLABXCNK-UHFFFAOYSA-N

物化性质

• 沸点：
  774.8±60.0 °C(Predicted)
• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  92.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2',2"-[methylidynetri(1H-pyrazol-1,3-diyl)]tris[6-bromopyridine] 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 生成 6,6',6''-[methylidynetri(1H-pyrazol-1,3-diyl)]tris[pyridine-2-carboxylic acid] dihydrochloride
  参考文献：
  名称：

  A convenient preparative method for anionic tris(substituted pyrazolyl)methane ligands

  摘要：

  The synthesis of tris[3-(6-carboxypyridin-2-yl)pyrazol-1-yl]methane is described in a linear multi-step protocol. The pyridyl-pyrazolyl arms are first constructed before being condensed with chloroform. Careful study of the condensation reaction shows the presence of an isomeric form of the tris(pyrazolyl)methane derivative in which one of the pyrazolyl substituents is linked through the nitrogen atom at the 2 position of the pyrazol. After acid-catalysed isomerisation to the desired isomer, the intermediate compound was subjected to a carboalkoxylation reaction and a subsequent hydrolysis. These are some rare examples of reactions directly occurring on the tris(pyrazolyl)methane platforms. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01506-5
• 作为产物：
  描述：

  2-bromo-6-(1H-pyrazol-1-yl)pyridine 在 triethylbenzyl ammonium chloride 、 sodium carbonate 、 对甲苯磺酸 作用下， 以 水 、 甲苯 为溶剂， 反应 34.0h， 生成 2,2',2"-[methylidynetri(1H-pyrazol-1,3-diyl)]tris[6-bromopyridine]
  参考文献：
  名称：

  A convenient preparative method for anionic tris(substituted pyrazolyl)methane ligands

  摘要：

  The synthesis of tris[3-(6-carboxypyridin-2-yl)pyrazol-1-yl]methane is described in a linear multi-step protocol. The pyridyl-pyrazolyl arms are first constructed before being condensed with chloroform. Careful study of the condensation reaction shows the presence of an isomeric form of the tris(pyrazolyl)methane derivative in which one of the pyrazolyl substituents is linked through the nitrogen atom at the 2 position of the pyrazol. After acid-catalysed isomerisation to the desired isomer, the intermediate compound was subjected to a carboalkoxylation reaction and a subsequent hydrolysis. These are some rare examples of reactions directly occurring on the tris(pyrazolyl)methane platforms. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01506-5

文献信息

• Anionically Substituted 1,1′,1″-Methylidynetris[1H-pyrazole] Ligands for the Formation of Neutral Lanthanide Complexes in Water: Synthesis, Characterization, and Photophysical Properties
  作者：Loïc J. Charbonnière、Raymond Ziessel

  DOI：10.1002/hlca.200390284

  日期：2003.10

  showed the Tb complex to be highly luminescent (ϕ=15%), while, for the Eu complex, the quantum efficiency was only 2%. Excited-state-lifetime measurements in H2O and D2O evidenced the presence of ca. three H2O molecules in the first coordination sphere of the complexes. Investigation of the Gd complex allowed the determination of the ligand-centered triplet state and showed the ligand to be well suited

  描述了新的豆荚型配体6,6'，6''-[亚甲基三（1 H-吡唑-1,3-二基）]三[吡啶-2-羧酸]（LH 3）的六步合成。的反应LH 3与LnCl 3  ⋅6ħ 2 O（LN =铕，钆，铽）在MeOH导致[LNL]⋅HCl络合物通过元素分析，质谱和IR光谱的隔离。Eu和Tb配合物在水溶液中的光物理研究表明，金属原子具有特征性的发光特征，这表明了有效的配体-金属能量转移过程。测定H 2 O中的发光量子产率表明Tb配合物具有高发光性（ϕ= 15％），而对于Eu络合物，量子效率仅为2％。在H 2 O和D 2 O中的激发态寿命测量结果证明了ca的存在。在配合物的第一个配位域中的三个H 2 O分子。对Gd配合物的研究可以确定以配体为中心的三重态，并表明该配体非常适合于能量转移至金属。描述了配合物的发光性质，并对作为合适的配合袋的配体的性质提出了质疑。
• A convenient preparative method for anionic tris(substituted pyrazolyl)methane ligands
  作者：Loı̈c J. Charbonnière、Raymond Ziessel

  DOI：10.1016/s0040-4039(03)01506-5

  日期：2003.8.11

  The synthesis of tris[3-(6-carboxypyridin-2-yl)pyrazol-1-yl]methane is described in a linear multi-step protocol. The pyridyl-pyrazolyl arms are first constructed before being condensed with chloroform. Careful study of the condensation reaction shows the presence of an isomeric form of the tris(pyrazolyl)methane derivative in which one of the pyrazolyl substituents is linked through the nitrogen atom at the 2 position of the pyrazol. After acid-catalysed isomerisation to the desired isomer, the intermediate compound was subjected to a carboalkoxylation reaction and a subsequent hydrolysis. These are some rare examples of reactions directly occurring on the tris(pyrazolyl)methane platforms. (C) 2003 Elsevier Ltd. All rights reserved.