2,5-(2-吡啶基)吡咯 | 60794-56-1

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 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
• 中文名称: 2,5-(2-吡啶基)吡咯
• 英文名称: 2-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)pyridine
• 英文别名: 2,5-bis(2'-pyridyl)pyrrole；2,5-di(2-pyridyl)pyrrole；2,5-Di(pyridin-2-yl)-1H-pyrrole；2-(5-pyridin-2-yl-1H-pyrrol-2-yl)pyridine
• CAS: 60794-56-1
• 化学式: C₁₄H₁₁N₃
• 分子量: 221.261
• InChiKey: HWLQJKMTFHIDBF-UHFFFAOYSA-N

物化性质

• 熔点：
  96 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  444.4±35.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 储存条件：
  存储在室温下

反应信息

• 作为反应物：
  描述：

  2,5-(2-吡啶基)吡咯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 24.0h， 生成 [(2,5-bis(α-pyridyl)-pyrrolate)Pd(OH₂)][OTf]
  参考文献：
  名称：

  Complexes of 2,5-Bis(α-pyridyl)pyrrolate with Pd(II) and Pt(II): A Monoanionic Iso-π-Electron Ligand Analog of Terpyridine

  摘要：

  Palladium and platinum metal complexes of 2,5-bis(alpha-pyridyl)-pyrrolate (PDP) are reported and characterized by spectroscopic methods, single-crystal X-ray diffraction, and elemental analysis. The single-crystal X-ray structures of these complexes exhibit structural features indicative of significant pi-backbonding. To illustrate the effect, bond lengths are statistically compared to unmetalated PDP and to a previously reported Zn(II) complex that exhibits no backbonding. Density functional theory calculations are used to aid understanding of the electronic structural basis of the observed phenomena.

  DOI：

  10.1021/ic300435t
• 作为产物：
  描述：

  diethyl 2,5-di(pyridin-2-yl)-1H-pyrrole-3,4-dicarboxylate 在 barium dihydroxide 作用下， 生成 2,5-(2-吡啶基)吡咯
  参考文献：
  名称：

  Hein; Melichar, Pharmazie, 1954, vol. 9, p. 455,460

  摘要：

  DOI：

文献信息

• Zinc complexes supported by pyridine-<i>N</i>-oxide ligands: synthesis, structures and catalytic Michael addition reactions
  作者：Xiu-Fang Mo、Chang-Feng Xiong、Ze-Wen Chen、Chao Liu、Piao He、Hai-Xia Tong、Xiao-Yi Yi

  DOI：10.1039/d0dt00185f

  日期：——

  New dipyridylpyrrole N-oxide ligands HL1 and HL2 are designed and synthesized via oxidation of 2-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)pyridine (Hdpp) by using 3-chloroperbenzoic acid (m-CPBA) in CH2Cl2. The treatment of ZnEt2 with two equiv. of HL1 and HL2 affords [Zn(L1)2] and [Zn(L2)2] in medium yield, respectively. These ligands and zinc complexes are fully characterized by NMR, IR, UV-vis and ESI-MS

  新dipyridylpyrrole Ñ氧化物配体和HL1 HL2是设计并合成通过2-（5-（吡啶-2-基）-1-氧化ħ通过使用3-氯过苯甲酸-吡咯-2-基）吡啶（HDPP）（米-CPBA）在CH 2 Cl 2中。ZnEt 2的处理具有两个当量。HL1和HL2分别以中等收率提供[Zn（L1）2 ]和[Zn（L2）2 ]。这些配体和锌络合物通过NMR，IR，UV-vis和ESI-MS光谱学和X射线衍射分析得到充分表征。HL1和HL2的结构显示为平面几何形状。亚氨基氢与氮之间的分子内氢键相互作用观察到-氧化氧原子。在[Zn（L1）2 ]和[Zn（L2）2 ]中，两个配体与垂直交叉的几何形状的锌金属螯合。锌络合物被用作在室温下在EtOH中将硫醇硫醇-迈克尔加成到α，β-不饱和酮上的高效催化剂。催化剂的负载降低到0.01摩尔％。基于NMR和ESI-MS实验提出了催化机理。
• Pyridazine and Pyrrole Compounds, Processes For Obtaining Them and Uses
  申请人：Dubreuil Didier Max

  公开号：US20100298562A1

  公开（公告）日：2010-11-25

  The present invention relates to nonlinear oligopyridazine compounds, to processes for obtaining them, to their uses, and also to their reduction to oligopyrroles and to the uses of the pyridazinylpyrrole and oligopyrrole compounds obtained. The invention relates in particular to the uses as medicaments, in particular for treating pathologies such as cancer, bacterial infections or parasitic infections, and also the uses in the materials, environmental, electronics and optics field.

  本发明涉及非线性寡吡啶化合物，以及获得它们的方法，它们的用途，以及将它们还原为寡吡咯和所获得的吡啶基吡咯和寡吡咯化合物的用途。该发明特别涉及用作药物的用途，特别是用于治疗癌症、细菌感染或寄生虫感染等病理的用途，以及在材料、环境、电子和光学领域的用途。
• Mono- and Dinuclear Binding Modes of the 2,5-Bis(α-pyridyl)pyrrolate Ligand in Platinum(II) Complexes
  作者：Drew C. Newman、Michael R. Gau、Patrick J. Carroll、Karen I. Goldberg

  DOI：10.1021/acs.organomet.1c00152

  日期：2021.6.28

  A series of platinum(II) complexes with the 2,5-bis(α-pyridyl)pyrrolate (PDP) ligand were synthesized. The ligand (X) trans to the central pyrrole nitrogen of PDP was found to play a key role in whether tridentate monomeric or bidentate clamshell dimer complexes were formed. When X = CH3 or C6H5, strong σ-donor ligands, only dimeric clamshell structures were observed. In contrast, when X = Cl or I

  合成了一系列具有 2,5-双(α-吡啶基)吡咯酸酯 (PDP) 配体的铂 (II) 配合物。发现与 PDP 的中心吡咯氮反式的配体 (X) 在三齿单体或双齿蛤壳二聚体复合物的形成中起关键作用。当 X = CH 3或 C 6 H 5 时，强σ-供体配体，仅观察到二聚蛤壳结构。相反，当 X = Cl 或 I，具有 π 供体特性的配体时，可以制备二聚体和单体复合物。配体框架支持与 π 供体 X 型配体形成单体复合物的能力归因于 PDP 配体在单体构象中充当有效 π 酸的能力。
• The syntheses, characterization and photophysical properties of phosphine copper(I) and silver(I) complexes with the bispyridylpyrrolide ligand
  作者：Ya-Ping Wang、Xiao-Hui Hu、Yi-Fan Wang、Jun Pan、Xiao-Yi Yi

  DOI：10.1016/j.poly.2015.10.057

  日期：2015.12

  Abstract Five mononuclear copper(I) complexes and one dinuclear silver(I) phosphine complex containing the bispyridylpyrrole ligand were synthesized and structurally characterized. Treatment of CuCl and the deprotonated bispyridylpyrrole ligand with bis(phosphine) ligands afforded the copper(I) complexes [(PDPH)Cu(XANTPhos)] (1), [(PDPH)Cu(DPEPhos)] (2), [(PDPBr)Cu(XANTPhos)] (3) and [(PDPBr)Cu(DPEPhos)]

  摘要合成了五种单核铜（I）配合物和一种含双吡啶基吡咯配体的双核银（I）膦配合物，并对其结构进行了表征。用双（膦）配体处理CuCl和去质子化的双吡啶基吡咯配体得到铜（I）配合物[（PDPH）Cu（XANTPhos）]（1），[（PDPH）Cu（DPEPhos）]（2），[（PDPBr ）Cu（XANTPhos）]（3）和[（PDPBr）Cu（DPEPhos）]（4），而同时添加两个等价的PPh3则得到[（PDPBr）Cu（PPh3）2]（5），其中PDPH− = 2 ，5-双（2-吡啶基）吡咯，PDPBr- = 2,5-双（6'-溴-2'-吡啶基）-吡咯，XANTPhos = 9,9-二甲基-4,5-双（二苯基膦基） x吨，DPEPhos =氧二-2,1-亚苯基）双-二苯基膦。PDPBr-与AgOTf和DPEPhos的反应产生了双核银（I）络合物[（PDPBr）Ag2（DPEPhos）]（O
• Neutral Complexes of First Row Transition Metals Bearing Unbound Thiocyanates and Their Assembly on Metallic Surfaces
  作者：Jacob W. Ciszek、Zachary K. Keane、Long Cheng、Michael P. Stewart、Lam H. Yu、Douglas Natelson、James M. Tour

  DOI：10.1021/ja055459d

  日期：2006.3.1

  coordination complexes designed to assemble on gold surfaces was synthesized, their electronic structure and transitions analyzed, and their magnetic properties studied. By taking advantage of recently developed thiocyanate assembly protocols, these molecules were then assembled onto a gold surface, without the need for an inert atmosphere, to give a loosely packed monolayer. The assembled molecules exhibit properties

  合成了一系列设计用于在金表面组装的过渡金属配位配合物，分析了它们的电子结构和跃迁，并研究了它们的磁性。通过利用最近开发的硫氰酸盐组装协议，这些分子被组装到金表面上，不需要惰性气氛，得到松散堆积的单层。组装的分子表现出与本体分子相似的特性，表明除化学吸附外分子结构几乎没有变化。