2,6-bis(3-bromomethyl-1-pyrazolyl)pyridine | 149558-66-7

• 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: 2,6-bis(3-bromomethyl-1-pyrazolyl)pyridine
• 英文别名: 2,6-Bis[3-(bromomethyl)pyrazol-1-yl]pyridine
• CAS: 149558-66-7
• 化学式: C₁₃H₁₁Br₂N₅
• 分子量: 397.072
• InChiKey: ITRIKMBPGKTKBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  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-bromomethyl-1-pyrazolyl)pyridine 在 palladium on activated charcoal sodium azide 、 氢气 作用下， 生成 2,6-bis(3-aminomethylpyrazol-1-yl)pyridine
  参考文献：
  名称：

  Synthesis of Novel Macrocyclic Lanthanide Chelates Derived from Bis-pyrazolylpyridine

  摘要：

  [GRAPHICS]New macrocyclic chelates based on bis-pyrazolylpyridine and diethylenetriaminepentaacetic acid are synthesized, and the remarkable luminescence properties of their lanthanide chelates are reported.

  DOI：

  10.1021/ol0169527
• 作为产物：
  描述：

  2,6-bis(3-ethoxycarbonyl-1-pyrazolyl)pyridine 在 lithium aluminium tetrahydride 、 三溴化磷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 6.0h， 生成 2,6-bis(3-bromomethyl-1-pyrazolyl)pyridine
  参考文献：
  名称：

  Remuinan, Modesto J.; Roman, Herminia; Alonso, Maria Teresa, Journal of the Chemical Society. Perkin transactions II, 1993, # 6, p. 1099 - 1102

  摘要：

  DOI：

文献信息

• Self-Aggregated Dinuclear Lanthanide(III) Complexes as Potential Bimodal Probes for Magnetic Resonance and Optical Imaging
  作者：Martín Regueiro-Figueroa、Aline Nonat、Gabriele A. Rolla、David Esteban-Gómez、Andrés de Blas、Teresa Rodríguez-Blas、Loïc J. Charbonnière、Mauro Botta、Carlos Platas-Iglesias

  DOI：10.1002/chem.201301231

  日期：2013.8.26

  characteristic of slowly tumbling systems, showing a low‐field plateau and a broad maximum around 30 MHz. This suggests the occurrence of aggregation of the complexes giving rise to slowly rotating species. A similar behavior is observed for the analogous GdIII complex containing a 4,4′‐dimethyl‐2,2′‐bipyridyl spacer ([Gd2(L1)]). The relaxivity of [Gd2(L3)] recorded at 0.5 T and 298 K (pH 6.9) amounts to 13.7 mM−1 s−1

  源自双大环配体的高模核镧系元素配合物（Ln = La，Eu，Gd，Tb，Yb和Lu），具有两个2,2'，2''-（1,4,7,10-四氮杂环十二烷-1,4制备并表征了通过2,6-双（吡唑-1-基）吡啶间隔基（H 2 L 3）连接的，7-三基）三乙酸螯合位点。在Eu III和Tb III配合物溶液上记录的发光寿命测量结果表明，在这些配合物中存在一个与每种金属离子配位的内层水分子。确定了整体的发光量子产率（φ = 0.01 [Eu的2（L 3）]和0.50 [TB 2（L 3）]在0.01 中号TRIS / HCl，pH 7.4；TRIS ＝三（羟甲基）氨基甲烷），指出配体的双吡唑基吡啶基单元，特别是Tb对金属离子的有效敏化。[Gd 2（L 3）]记录的核磁弛豫色散（NMRD）曲线是缓慢滚动系统的特征，显示出低场平稳区和30 MHz附近的宽最大值。这表明复合物发生聚集，从而产生缓慢旋转的物质。对于包含4
• Multifunctionalized luminescent lanthanide complexes from nonadentate phosphonylated bis-pyrazolyl-pyridine ligands
  作者：Matthieu Starck、Raymond Ziessel

  DOI：10.1039/c2dt31181j

  日期：——

  A series of lanthanide complexes has been prepared from ligands constructed from a bis-pyrazolyl-pyridine core bearing various chelating arms with anionic mixed carboxylate/phosphonate or phosphonate substituents. These ligands form particularly stable complexes with Eu(III) and Tb(III) which display outstanding spectroscopic properties, with excited state lifetimes ranging from 2.6 to 3.2 ms and quantum yields in the 16 to 48% range in water or phosphate buffer. The complexes are significantly more stable than those of analogous ligands bearing only carboxylate groups. Some of the new ligands have a central and flexible pendent link suitable for bio-labelling.

  一系列镧系元素配合物是由双吡唑基吡啶核心配体与带有阴离子混合羧酸盐/膦酸盐或膦酸盐取代基的各种螯合臂制备而成的。这些配体与 Eu(III)和 Tb(III)形成特别稳定的配合物，显示出卓越的光谱特性，在水或磷酸盐缓冲液中的激发态寿命为 2.6 至 3.2 毫秒，量子产率为 16% 至 48%。这些配合物的稳定性明显高于只含有羧基的类似配体。其中一些新配体具有适用于生物标记的中心和柔性悬垂连接。
• Lanthanide complexes of new polyaminocarboxylate complexes with two chromophores derived from bispyrazolylpyridine and aceto or benzophenone: synthesis, characterization and photophysical properties
  作者：Ernesto Brunet、Olga Juanes、Rosa Sedano、Juan Carlos Rodrı́guez-Ubis

  DOI：10.1016/j.tet.2005.05.009

  日期：2005.7

  New ionophores derived from 2,6-bis(N-pyrazolyl)pyridine and aceto/benzophenone have been synthesized and fully characterized. The lanthanide complexes of these new ligands were studied from their UV–vis and fluorescence data. Eu3+ and Tb3+ complexes were easily formed and their photophysical properties measured. In all cases, lanthanide emission lifetimes were in the range of ms albeit quantum yields

  合成并充分表征了衍生自2，6-双（N-吡唑基）吡啶和乙酰/二苯甲酮的新离子载体。这些新的配体的镧系元素络合物是从它们的紫外可见和荧光数据中进行研究的。容易形成Eu 3+和Tb 3+配合物，并测量其光物理性质。在所有情况下，尽管量子产率相对较低，但镧系元素的发射寿命都在ms的范围内。讨论了能量传递机制中可能存在的缺陷。
• New Macrobicycles Containing a Tetralactam Moiety: Template Synthesis and Study of their Binding with Lanthanides
  作者：Joëlle Azéma、Chantal Galaup、Claude Picard、Pierre Tisnès、Patricia Ramos、Olga Juanes、Juan Carlos Rodrı́guez-Ubis、Ernesto Brunet

  DOI：10.1016/s0040-4020(00)00164-2

  日期：2000.4

  The synthesis of macrobicyclic cryptands 1, 2 from an 18-membered diazatetralactam and 6,6'-bis(bromomethyl)-2,2'-bipyridine or 2,6-bis(3-bromomethy1-1-pyrazolyl)pyridine has been investigated using various metal carbonates. The analysis of the distribution products by gel permeation chromatography showed that macrocyclization process was markedly conditioned by cation template effects. Optimum yields were obtained for Li+ and Na+ in the preparation of 1 and 2, respectively. The cryptate structure of the corresponding complexes of Ln(III) (Ln=Eu, Tb, Gd) is discussed on the basis of spectroscopic and photophysical data. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Remuinan, Modesto J.; Roman, Herminia; Alonso, Maria Teresa, Journal of the Chemical Society. Perkin transactions II, 1993, # 6, p. 1099 - 1102
  作者：Remuinan, Modesto J.、Roman, Herminia、Alonso, Maria Teresa、Rodriguez-Ubis, Juan C.

  DOI：——

  日期：——