4'-methyl-(2,2'-bipyridine)-4-carboxylic acid propargyl amide | 220715-46-8

• 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'-methyl-(2,2'-bipyridine)-4-carboxylic acid propargyl amide
• 英文别名: 4'-methyl-2,2'-bipyridine-4-propargylamide；4'-methyl-2,2'-bipyridine-4-carbonyl-N-propargyl amine；4'-Methyl-2,2'-bipyridine-4-carbonyl propargyl amine；2-(4-methylpyridin-2-yl)-N-prop-2-ynylpyridine-4-carboxamide
• CAS: 220715-46-8
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: ITVXBXVLKRKYPC-UHFFFAOYSA-N

物化性质

• 沸点：
  459.6±45.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4'-methyl-(2,2'-bipyridine)-4-carboxylic acid propargyl amide 、 三氯化钌 以 ethanol 、 acetic acid 为溶剂， 以39%的产率得到
  参考文献：
  名称：

  通过点击化学轻松合成尺寸依赖性Ru（II）-碳水化合物树状聚合物。

  摘要：

  描述了一种基于Cu（II）催化的Huisgen- [3 + 2]环加成反应制备包含不同碳水化合物的Ru（II）配合物的简便灵活的方法。

  DOI：

  10.1039/b925113h
• 作为产物：
  描述：

  4,4'-二甲基-2,2'-联吡啶 在 selenium(IV) oxide 、 1-羟基苯并三唑 、 silver nitrate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 4'-methyl-(2,2'-bipyridine)-4-carboxylic acid propargyl amide
  参考文献：
  名称：

  Synthesis and Electrocatalytic Water Oxidation by Electrode-Bound Helical Peptide Chromophore–Catalyst Assemblies

  摘要：

  Artificial photosynthesis based on dye-sensitized photoelectrosynthesis cells requires the assembly of a chromophore and catalyst in close proximity on the surface of a transparent, high band gap oxide semiconductor for integrated light absorption and catalysis. While there are a number of approaches to assemble mixtures of chromophores and catalysts on a surface for use in artificial photosynthesis based on dye-sensitized photoelectrosynthesis cells, the synthesis of discrete surface-bound chromophore catalyst conjugates is a challenging task with few examples to date. Herein, a versatile synthetic approach and electrochemical characterization of a series of oligoproline-based light-harvesting chromophore water-oxidation catalyst assemblies is described. This approach combines solid-phase peptide synthesis for systematic variation of the backbone, copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) as an orthogonal approach to install the chromophore, and assembly of the water-oxidation catalyst in the final step. Importantly, the catalyst was found to be incompatible with the conditions both for amide bond formation and for the CuAAC reaction. The modular nature of the synthesis with late-stage assembly of the catalyst allows for systematic variation in the spatial arrangement of light-harvesting chromophore and water-oxidation catalyst and the role of intrastrand distance on chromophore catalyst assembly properties. Controlled potential electrolysis experiments verified that the surface-bound assemblies function as water-oxidation electrocatalysts, and electrochemical kinetics data demonstrate that the assemblies exhibit greater than 10-fold rate enhancements compared to the homogeneous catalyst alone.

  DOI：

  10.1021/ic5011488

文献信息

• Tunable Energy Transfer Rates via Control of Primary, Secondary, and Tertiary Structure of a Coiled Coil Peptide Scaffold
  作者：Dale J. Wilger、Stephanie E. Bettis、Christopher K. Materese、Maria Minakova、Garegin A. Papoian、John M. Papanikolas、Marcey L. Waters

  DOI：10.1021/ic300669t

  日期：2012.11.5

  we report energy transfer studies in a series of Ru(II) and Os(II) linked coiled-coil peptides in which the supramolecular scaffold controls the functional properties of the assembly. A general and convergent method for the site-specific incorporation of bipyridyl Ru(II) and Os(II) complexes using solid-phase peptide synthesis and the copper-catalyzed azide–alkyne cycloaddition is reported. Supramolecular

  本文中，我们报告了一系列Ru（II）和Os（II）连接的卷曲螺旋肽中的能量转移研究，其中超分子支架控制装配的功能特性。据报道，使用固相肽合成法和铜催化的叠氮化物-炔烃环加成反应，可将位点特异性掺入联吡啶Ru（II）和Os（II）配合物的通用方法。超分子组装定位发色团以进行能量转移。使用时间分辨发射光谱，我们测量了位置依赖性能量传递，该能量传递可通过肽支架序列的变化而变化。高水平的分子动力学模拟与光谱技术结合使用，可以从分子水平上洞悉所观察到的能量转移趋势。k EnT = 2.3×10 7 s –1（42 ns））。另外，Ru（II）和Os（II）肽的发射猝灭可以适合于结合模型，该模型与通过化学变性为肽确定的解离常数相符。
• Light‐Activated Carbon Monoxide Prodrugs Based on Bipyridyl Dicarbonyl Ruthenium(II) Complexes
  作者：Stepan Geri、Tereza Krunclova、Olga Janouskova、Jiri Panek、Martin Hruby、Daniel Hernández‐Valdés、Benjamin Probst、Roger A. Alberto、Constantin Mamat、Manja Kubeil、Holger Stephan

  DOI：10.1002/chem.202002139

  日期：2020.8.26

  Two photoactivatable dicarbonyl ruthenium(II) complexes based on an amide‐functionalised bipyridine scaffold (4‐position) equipped with an alkyne functionality or a green‐fluorescent BODIPY (boron‐dipyrromethene) dye have been prepared and used to investigate their light‐induced decarbonylation. UV/Vis, FTIR and 13C NMR spectroscopies as well as gas chromatography and multivariate curve resolution

  制备了两种基于配备炔官能团或绿色荧光 BODIPY（硼-二吡咯亚甲基）染料的酰胺官能化联吡啶支架（4 位）的光活化二羰基钌（II）配合物，并用于研究其光诱导脱羰作用。UV/Vis、FTIR 和13 C NMR 光谱以及气相色谱和多元曲线分辨率交替最小二乘分析 (MCR-ALS) 用于阐明脱羰过程的机制。第一个 CO 分子的释放发生得非常快，而第二个 CO 分子的释放则进行得更慢。为了表征抗增殖和抗凋亡活性，已经使用两种细胞系 A431（人鳞状细胞癌）和 HEK293（人胚胎肾细胞）进行了体外研究。BODIPY 标记的化合物可以监测细胞的摄取，显示出快速的内化动力学以及在内质网和线粒体处的积累。
• Nucleic acid probes and methods
  申请人：Duke University

  公开号：US20020177695A1

  公开（公告）日：2002-11-28

  The present invention provides metal-containing purines, pyrimidines, nucleosides, nucleotides and oligonucleotides; including phosphoramidite and photolabile derivatives thereof, including methods of making and method of using same. The present invention provides a method for detection of nucleic acid sequences via electrochemical or photochemical means.

  本发明提供了含金属的嘌呤、嘧啶、核苷、核苷酸和寡核苷酸，包括其磷酰胺酰基和光致裂解衍生物，以及制备和使用它们的方法。本发明还提供了一种通过电化学或光化学手段检测核酸序列的方法。
• Methods of synthesis of halogen base-modified oligonucleotides and subsequent labeling with a metal-catalyzed reaction
  申请人：Duke University

  公开号：US06288221B1

  公开（公告）日：2001-09-11

  The present invention provides metal-containing purines, pyrimidines, nucleosides, nucleotides and oligonucleotides; including phosphoramidite and photolabile derivatives thereof, including methods of making and method of using same. The present invention provides a method for detection of nucleic acid sequences via electrochemical or photochemical means.

  本发明提供了含金属的嘌呤、嘧啶、核苷、核苷酸和寡核苷酸，包括其磷酰胺酯和光致裂解衍生物，以及制备和使用它们的方法。本发明提供了一种通过电化学或光化学手段检测核酸序列的方法。
• Interfacial Energy Conversion in Ru^II Polypyridyl-Derivatized Oligoproline Assemblies on TiO₂
  作者：Da Ma、Stephanie E. Bettis、Kenneth Hanson、Maria Minakova、Leila Alibabaei、William Fondrie、Derek M. Ryan、Garegin A. Papoian、Thomas J. Meyer、Marcey L. Waters、John M. Papanikolas

  DOI：10.1021/ja312143h

  日期：2013.4.10

  Solid-phase peptide synthesis has been applied to the preparation of phosphonate-derivatized oligoproline assemblies containing two different Ru-II polypyridyl chromophores coupled via "click" chemistry. In water or methanol the assembly adopts the polyproline II (PPII) helical structure, which brings the chromophores into close contact. Excitation of the assembly on ZrO2 at the outer Ru-II in 0.1 M HClO4 at 25 degrees C is followed by rapid, efficient intra-assembly energy transfer to the inner Ru-II (k(EnT) = 3.0 x 10(7) s(-1), implying 96% relative efficiency). The comparable energy transfer rate constants in solution and on nanocrystalline ZrO2 suggest that the PPII structure is retained when bound to ZrO2. On nano crystalline films of TiO2, excitation at the inner Ru-II is followed by rapid, efficient injection into TiO2. Excitation of the outer Ru-II is followed by rapid intra-assembly energy transfer and then by electron injection. The oligoproline/click chemistry approach holds great promise for the preparation of interfacial assemblies for energy conversion based on a family of assemblies having controlled compositions and distances between key functional groups.