5-乙炔基-2-吡啶-2-基吡啶 | 162318-34-5

• 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: 5-乙炔基-2-吡啶-2-基吡啶
• 中文别名: 5-乙炔基-2,2'-联吡啶
• 英文名称: 5-ethynyl-2,2'-bipyridine
• 英文别名: 5-ethynyl-2,2’-bipyridine；5-ethynyl-2,2′-bipyridine；5-ethynyl-2-pyridin-2-ylpyridine
• CAS: 162318-34-5
• 化学式: C₁₂H₈N₂
• 分子量: 180.209
• InChiKey: RQXYJBJCQSECMR-UHFFFAOYSA-N

物化性质

• 熔点：
  87-89 °C
• 沸点：
  312.4±32.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  5-乙炔基-2-吡啶-2-基吡啶 在 NEt₃ 作用下， 以 二氯甲烷 为溶剂， 生成 [Au(CC-2,2'-bipyridine-5-yl)(PEt3)]
  参考文献：
  名称：

  Synthesis of Luminescent Alkynyl Gold Metalaligands Containing 2,2′-Bipyridine-5-yl and 2,2′:6′,2′′-Terpyridine-4-yl Donor Groups

  摘要：

  [AuCl(SMe2) reacts with HC CR (R = bpyl = 2,2'-bipyridine-5-yl (1), phtpyl phenyl-4-(2,2': 6',2 ''-terpyridine-4-yl) (2)) and NEt3 (1:1:3) to afford the polymers [Au(C CR)](n) (R bpyl (3), phtpyl (4)). The new alkyne HC Cphccbpyl (5, phccbpyl = 4-C6H4C Cbpyl) has been prepared by Sonogashira coupling of 4-Me3SiC CC6H4I and I followed by desilylation of the resulting alkyne 4-Me3SiC Cphccbpyl. The alkynyl Au(I) complexes [Au(C CR)L] (R = bpyl, L = PPh3 (6), PTol(3) (7, Tol = 4-MeC6H4), PEt3 (8); R = phtpyl, L = XyNC (9), PPh3 (10); R = phccbpyl, L = PPh3 (11)) have been prepared by reacting: (1) 3 or 4 with L or (2) the corresponding alkyne 1, 2, or 5 with [Au(acac)(PPh3)] (acac = acetylacetonato). The reaction of 3 or 4 with diphosphines ,gives [(Au(C CR)}(2)(mu-Ph2P(CH2)(x)PPh2)] (R = bpyl, x = 1 (12), 2 (13), 4 (14), 10 (15); R = phtpyl, x = 10 (16)). ESI mass spectrometric studies show that complexes 12-14 are in equilibrium with the salts [Au-3(C Cbpyl)(2)(mu-Ph2P(CH2)(x)PPh2)(2)][Au(C Cbpyl)(2)], although only when x = 1 (17) was a significant concentration of the salt detected by NMR spectroscopy and isolated. The anionic complexes PPN[Au(C CR)(2)] (R = bpyl (18), phtpyl (19), or phccbpyl (20)) have been prepared by reaction of the corresponding alkynes with PPN[Au(acac)(2)]. Complexes 6, 10, 13, 14, 17, and 18 have been characterized by sing e-crystal X-ray diffraction studies. The alkynyl complexes are luminescent at room temperature, displaying dual emissions.

  DOI：

  10.1021/om7009123
• 作为产物：
  描述：

  2-(三甲基甲锡烷基)吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 间二甲苯 为溶剂， 反应 40.0h， 生成 5-乙炔基-2-吡啶-2-基吡啶
  参考文献：
  名称：

  Electrochemiluminescent dinuclear Ru(II) complexes assembled with 1,1′-(1,2-ethynediyl)- or dimethlyene-bridged bis(bipyridine) ligands: Synthesis and photophysical and electrochemical properties

  摘要：

  1,2-Di(2,2'-bipyridin-5-yl) ethane (BL1) and 1,2-di(2,2'-bipyridin-5-yl)ethyne (BL2) were synthesized as new bridging ligands and coordinated to (RuL2(acetone)(2))(PF6)(2) for the preparation of various [Ru(L)(2) (BL) Ru(L)(2)](PF6)(4)-type dinuclear ruthenium complexes (where BL = BL1, BL2 and L = bpy, o-phen, DTDP). The electrochemical redox potentials, spectroscopic properties, and relative electrochemiluminescence intensity of BL1 and BL2 were characterized and compared to those of well-known tris(1,10-phenanthroline) rutheniun(II) [Ru(o-phen)(3)](PF6)(2)] complex as a reference. Dinuclear Ru(II) complexes containing the conjugated bridging ligand (BL2) showed much more intense electrochemiluminescent responses than dinuclear Ru(II) complexes with the non-conjugated bridging ligand (BL1). Among the complexes with conjugated bridging ligands, [(DTDP)(2)Ru(bpy-CC-bpy)Ru(DTDP)(2)](PF6)(4) exhibited enhanced ECL intensities as high as 3.6 times greater than that of the reference, [Ru(o-phen)(3)](PF6)(2). (C)2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.10.028

文献信息

• Heteromultimetallic Transition Metal Complexes Based on Unsymmetrical Platinum(II) Bis-Acetylides
  作者：Rico Packheiser、Petra Ecorchard、Tobias Rüffer、Heinrich Lang

  DOI：10.1021/om800232m

  日期：2008.7.1

  The synthesis of a unique series of heteromultinuclear transition metal complexes with up to seven different metal atoms is reported by using consecutive synthesis methodologies including metathesis, dehydrohalogenation, and carbon−carbon cross-coupling reactions. In these compounds the metals Ti, Fe, Ru, Os, Re, Pt, and Cu are connected via carbon-rich bridging units comprising 1,3,5-triethynylbenzene

  通过使用包括复分解，脱氢卤化和碳-碳交叉偶联反应在内的连续合成方法，报道了具有多达七个不同金属原子的一系列独特的杂多核过渡金属配合物的合成。在这些化合物中，金属Ti，Fe，Ru，Os，Re，Pt和Cu通过富含碳的桥接单元连接，该桥接单元包括1,3,5-三乙炔基苯和2,2'-联吡啶基-5-基。这些分子已通过元素分析，IR和NMR光谱以及ESI-TOF质谱进行了表征。这些化合物的主要结构特征是不对称的反式构型的铂（II）双乙炔化物单元。的1-（FcC≡C）的结构的-3 - [（吨卜2联吡啶）（CO）3 ReC≡C] -5- [反式- （PH 3 P）2（RcC≡C）PtC≡C]Ç 6 ħ 3（3）和1,3 - 〔（PH 3 P）2（η 5 -C 5 H ^ 5）OsC≡C] 2 - 5 - [（CO）3（Cl）的重（bpyC≡C）] c ^ 6 ħ 3（18）（FC =（η 5 -C 5 H ^
• Heterometallic Complexes with Gold(I) Metalloligands: Self-Assembly of Helical Dimers Stabilized by Weak Intermolecular Interactions and Solvophobic Effects
  作者：Verónica Cámara、Natalia Barquero、Delia Bautista、Juan Gil-Rubio、José Vicente

  DOI：10.1002/chem.201405487

  日期：2015.1.26

  New gold(I) alkynyl metalloligands bpylCCAuL, bpyl′CCAuPPh3, and PPN[Au(CCbpyl′)2] (bpyl or bpyl′=2,2′‐bipyridin‐5‐yl or −4‐yl, respectively; L=PMexPh3−x (x=1–3), P(C6H3Me2‐3,5)3, PCy3, XyNC) have been synthesized. Ligands bpylCCH and metalloligands bpylCCAuL (L=PPh3, PMePh2, PCy3, CNXy) react with MX2 (M=Fe, Zn, X=ClO4; M=Co, X=BF4) to give complexes [M(bpylCCZ)3]X2 (Z=H or AuL). In most cases

  新金（I）炔基metalloligandsbpylCCAuL，bpyl'CCAuPPh 3，和PPN [AU（CCbpyl'）2 ]（bpyl或bpyl'= 2,2'-联吡啶-5-基或-4-基，分别为：L = PME X博士3- X（X = 1〜3），P（C 6 H ^ 3我2 -3,5-）3，PCY 3，XyNC）已经被合成。配体bpylCCH和金属配体bpylCCAuL（L = PPh 3，PMePh 2，PCy 3，CNXy）与MX 2（M = Fe，Zn，X = ClO 4 ; M = Co，X = BF 4）反应生成配合物[M（bpylCCZ）3 ] X 2（Z = H或AuL）。在大多数情况下，这些络合物是CH 2 Cl 2和MeCN中呈统计分布的fac和mer异构体的混合物。但是，对于L = PPh 3，fac异构体在MeCN中占主导地位。NMR和ESI-MS研究
• Preparation and properties of thienyl and 2,2′-bithienyl substituted cobalt-bis(semiquinone) valence tautomers
  作者：Thomas J. O’Sullivan、Brandon Djukic、Paul A. Dube、Martin T. Lemaire

  DOI：10.1139/v09-012

  日期：2009.4

  The synthesis and characterization of two new 2,2′-bipyridine ligands containing 3-ethynylthiophene and 3,3′-diethynyl-2,2′-bithiophene substituents is presented, along with the preparation, electronic, and magnetic properties of mono- and bimetallic cobalt-semiquinone valence tautomers containing these ligands.

  本文介绍了含有 3- 乙炔基噻吩和 3,3′- 二乙炔基-2,2′-噻吩取代基的两种新的 2,2′- 联吡啶配体的合成和表征，以及含有这些配体的单金属和双金属钴-半醌价同系物的制备、电子和磁性能。
• Lowering Electrocatalytic CO₂ Reduction Overpotential Using N-Annulated Perylene Diimide Rhenium Bipyridine Dyads with Variable Tether Length
  作者：Josh D. B. Koenig、Zachary S. Dubrawski、Keerthan R. Rao、Janina Willkomm、Benjamin S. Gelfand、Chad Risko、Warren E. Piers、Gregory C. Welch

  DOI：10.1021/jacs.1c09481

  日期：2021.10.13

  CO2 reduction; only at Eappl = −2.1 V vs Fc+/0 could Re(dmbpy) achieve the same catalytic performance, representing a 300 mV lowering in overpotential for Re(bpy-C2/4/6-NPDI). At higher overpotentials, Re(bpy-C4/6-NPDI) both outperformed Re(bpy-C2-NPDI), indicating the possibility of coinciding electrocatalytic CO2 reduction mechanisms that are dictated by tether-length and overpotential. Using UV-vis-nearIR

  我们报告了四种 N 环化苝二亚胺 (NPDI) 功能化铼联吡啶 [Re(bpy)] 超分子二元组的设计、合成和表征。Re(bpy) 支架直接连接到 NPDI 发色团 [ Re(py-C0-NPDI) ] 或通过乙基 [ Re(bpy-C2-NPDI) ]、丁基 [ Re(bpy-C4-NPDI) ] ，或己基 [ Re(bpy-C6-NPDI) ] 烷基链间隔基。在CO 2和质子源存在下进行电化学还原时，Re(bpy-C2/4/6-NPDI)均表现出显着的电流增强效果，而Re(py-C0-NPDI) 则没有。在E appl = -1.8 V vs Fc 的受控电位电解 (CPE) 实验期间+/- 0、Re(bpy-C2/4/6-NPDI)都达到了相当的活性（TON co ∼ 25）和法拉第效率（FE co ∼ 94%）。在相同的 CPE 条件下，标准催化剂 Re(dmbpy) 对电催化 CO
• Selective Reduction of CO₂ to CO by a Molecular Re(ethynyl-bpy)(CO)₃Cl Catalyst and Attachment to Carbon Electrode Surfaces
  作者：Almagul Zhanaidarova、Andrew L. Ostericher、Christopher J. Miller、Simon C. Jones、Clifford P. Kubiak

  DOI：10.1021/acs.organomet.8b00547

  日期：2019.3.25

  preliminary studies, these electrodes show promise as heterogeneous electrocatalysts. Further optimization and understanding of deactivation pathways will be required to make these systems practical. The ethynyl functionalized Re(ethynyl-bpy)(CO)3Cl catalyst also can be attached to graphitic carbon electrodes through the “click” reaction. This represents the first example of attachment of a CO2 reduction

  研究了Re（乙炔基-bpy）（CO）3 Cl和Re（乙烯基-bpy）（CO）3 Cl的催化性能，并与以前报道的Re（tBu-bpy））CO）3 Cl进行了比较。作为分子催化剂，Re（乙炔基-bpy）（CO）3 Cl将CO 2还原为具有较低的过电势（η≈0.525 V），较高的CO选择性（FE 96％）和较高的反应速率（I cat / I p = 27）与迄今报道的类似催化剂相比。催化剂在干燥乙腈溶液中的玻璃碳电极表面进行电聚合，从而形成在CO 2下具有电活性的聚合物膜气氛。在三氟乙醇（TFE）（p K a 35.4，MeCN）存在下，这些薄膜显示出高的CO效率（FE CO 97％）。在初步研究的基础上，这些电极显示出有望用作非均相电催化剂。为了使这些系统实用，将需要进一步优化和了解失活途径。乙炔基官能化的Re（ethynyl-bpy）（CO）3 Cl催化剂也可以通过“点击”反应连接到石墨碳电极上。这代表了通过“滴答”化学将CO