4-(pyrrolidin-1-yl)-2-(4-(pyrrolidin-1-yl)pyridin-2-yl)pyridine | 874758-86-8

• 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: 4-(pyrrolidin-1-yl)-2-(4-(pyrrolidin-1-yl)pyridin-2-yl)pyridine
• 英文别名: 4,4’-dipyrrolidino-2,2’-bipyridine；4,4'-bis-(N-pyrrolidino)-2,2'-bipyridyl；pyrrid2bpy；4,4'-Di-pyrrolidin-1-yl-[2,2']bipyridinyl；4-pyrrolidin-1-yl-2-(4-pyrrolidin-1-ylpyridin-2-yl)pyridine
• CAS: 874758-86-8
• 化学式: C₁₈H₂₂N₄
• 分子量: 294.399
• InChiKey: PMGICETZCRYDBB-UHFFFAOYSA-N

物化性质

• 熔点：
  210 °C
• 沸点：
  524.2±50.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  32.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(pyrrolidin-1-yl)-2-(4-(pyrrolidin-1-yl)pyridin-2-yl)pyridine 在 三乙胺 作用下， 以 乙醇 、 水 、 乙二醇 为溶剂， 反应 4.12h， 生成 {Ru[4,4’-dipyrrolidino-2,2’-bipyridine]2(4,4′-dicarboxylicacid-2,2′-bipyridine)}(PF6)2
  参考文献：
  名称：

  Zinc oxide nanocrystal quenching of emission from electron-rich ruthenium-bipyridine complexes

  摘要：

  异配三(联吡啶)钌配合物带有一个二羧基联吡啶配体，能够结合到分散的ZnO纳米晶体上。其余联吡啶上的电子释放性氨基取代基使得激发态能级高到足以允许激发态电子转移进入ZnO。

  DOI：

  10.1039/c4dt03272a
• 作为产物：
  描述：

  4-吡咯烷基吡啶 在 bis-triphenylphosphine-palladium(II) chloride 正丁基锂 、 N,N-二甲基乙醇胺 、 三苯基膦 作用下， 以 正己烷 、 xylene 为溶剂， 反应 23.0h， 生成 4-(pyrrolidin-1-yl)-2-(4-(pyrrolidin-1-yl)pyridin-2-yl)pyridine
  参考文献：
  名称：

  Pyrrolidine-Containing Polypyridines: New Ligands for Improved Visible Light Absorption by Ruthenium Complexes

  摘要：

  A range of new electron-releasing pyrrolidine-containing bipyridines and terpyridines has been prepared via selective metalation-cross-coupling sequences. The obtained ligands have been involved in microwave-assisted ruthenium complexation leading to homoleptic complexes in high yield. The electron-donor effect of the pyrrolidine nucleus led to a notable improvement of visible light absorption and strong changes in the electrochemical behavior, opening new opportunities for the design of photovoltaic devices.

  DOI：

  10.1021/jo051994k

文献信息

• Anticancer activity of ruthenium(II) polypyridine complexes bearing pyrrolidine substituents
  作者：Olga Mazuryk、Michał Łomzik、David Martineau、Marc Beley、Małgorzata Brindell、Grażyna Stochel、Philippe C. Gros

  DOI：10.1016/j.ica.2015.12.021

  日期：2016.3

  Abstract A set of homoleptic ruthenium polypyridine (bipyridine and terpyridine) complexes flanked with several electron-donating pyrrolidine moieties has been characterized and the anticancer activity was evaluated toward human lung adenocarcinoma epithelial (A549) and murine colon carcinoma (CT26). Good antiproliferative effects were observed with an IC 50 ranging from ca. 4 to 21 μM against both

  摘要表征了一组均化的钌多吡啶（联吡啶和三联吡啶）配合物，其侧翼带有多个供电子吡咯烷部分，并评估了其对人肺腺癌上皮细胞（A549）和鼠结肠癌（CT26）的抗癌活性。用约50的IC 50观察到良好的抗增殖作用。两种细胞系的抗氧化能力均为4至21μM。发现在细胞毒性，亲脂性和Ru II / Ru III氧化电位之间存在依赖性。所有研究的化合物与白蛋白的相互作用都很好，而与DNA的相互作用很小。生物学研究表明，钌络合物可诱导ROS过度生成，这可能是诱导细胞死亡的一种方法，但不是唯一的方法。
• An efficient Negishi cross-coupling reaction catalyzed by nickel(II) and diethyl phosphite
  作者：Andrei Gavryushin、Christiane Kofink、Georg Manolikakes、Paul Knochel

  DOI：10.1016/j.tet.2006.03.123

  日期：2006.8

  A combination of diethyl phosphite-DMAP and Ni(II) salts forms a very effective catalytic system for the cross-coupling reactions of arylzinc halides with aryl, heteroaryl, and alkenyl bromides. chlorides. triflates. and nonaflates. The choice of solvent is quite important and the mixture of THF-N-ethylpyrrolidinone (NEP) (8: 1) was found to be optimal. The reaction usually requires only 0.05 moll % of NiCl2 or Ni(acac)(2) as catalyst and proceeds at room temperature within 1-48 h. (c) 2006 Elsevier Ltd. All rights reserved.
• Tuning of Ruthenium Complex Properties Using Pyrrole- and Pyrrolidine-Containing Polypyridine Ligands
  作者：David Martineau、Marc Beley、Philippe C. Gros、Silvia Cazzanti、Stefano Caramori、Carlo A. Bignozzi

  DOI：10.1021/ic062042f

  日期：2007.3.1

  The effect of pyrrole- and pyrrolidine-containing ligands (L) on the properties of heteroleptic [RuL(2)dcbpy](2+) complexes has been investigated. TiO2 electrodes modified with the new complexes exhibited extended absorption domains and high absorbances. Providing that a cobalt-based mediator was used for regeneration of the Ru-II state, good incident photon-to-current efficiency (near 80%) values were obtained in the pyrrole series.
• Designing Ionic Ir(III) Cyclometalated Complexes as Photocatalysts for Light Assisted ATRP of MMA. A Combined Experimental and Mechanistic Study
  作者：Giulia Vigarani、Edoardo Marchini、Eleonora Previati、Loris Giorgini、Stefano Zacchini、Roberto Argazzi、Massimiliano Massi、Valentina Fiorini、Stefano Caramori、Stefano Stagni

  DOI：10.1002/chem.202400393

  日期：2024.5.8

  A new family of ionic Ir(III) cyclometalated complexes with general formula [Ir(CN)2(NN)][Br], was designed and prepared to be assessed as photocalysts for the visible light assisted ATRP polymerization of MMA. To this purpose, our design strategy involved both: i) the decoration of the cyclometalating (CN) and the ancillary (NN) ligands with various electron withdrawing and/or electron donor substituents and, ii) the use of Br− as the counter anion for these cationic Ir(III) species. After an extensive screening in which the [Ir(CN)2(NN)][Br]‐type compounds were compared to the model neutral complex fac‐[Ir(ppy)3], the “fully” amino‐substituted ion pairs abbreviated as [10][Br] and [11][Br], exhibited the best photocatalytic performances under irradiation with CFL lamps. It is worth noting that the outcomes of transient absorption spectroscopy (TAS) experiments combined with theoretical DFT calculations, enlightened the role played by the Ir(III) complexes in the mechanism of the photoATRP process, and suggested the rationalization of the different performances that were highlighted by our Ir(III) catalyst in the visible light assisted photopolymerization of MMA.
• CN115417809
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