4,4',6,6'-四甲基-2,2'-联吡啶 | 4444-27-3

• 物质功能分类: 有机原料 - 杂环化合物
• 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: 4,4',6,6'-四甲基-2,2'-联吡啶
• 中文别名: 4,4',6,6'-四甲基-2,2‘-联吡啶
• 英文名称: 4,4',6,6'-tetramethyl-2,2'-bipyridine
• 英文别名: 4,4′,6,6′-tetramethyl-2,2′-bipyridine；4,4’,6,6’-tetramethyl-2,2’-bipyridine；2-(4,6-dimethylpyridin-2-yl)-4,6-dimethylpyridine
• CAS: 4444-27-3
• 化学式: C₁₄H₁₆N₂
• 分子量: 212.294
• InChiKey: SMLORZJGJAWILX-UHFFFAOYSA-N

物化性质

• 熔点：
  142.5-143.0 °C(Solv: ligroine (8032-32-4))
• 沸点：
  307.4±37.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  4,4',6,6'-四甲基-2,2'-联吡啶 在 硝酸 作用下， 以 水 为溶剂， 生成 2,2'-联吡啶
  参考文献：
  名称：

  Acid directed in situ oxidation and decarboxylation of 4,4′,6,6′-tetra-methyl-2,2′-bipyridine: Synthesis and structural characterisation of 4,4′,6-tri-carboxy-2,2′-bipyridine and its copper(II) coordination polymer

  摘要：

  The reaction of either 4,4',6,6'-tetramethyl-2,2'-bipyridine, L, or 4,4',6,6'-tetracarboxy-2,2'-bipyridine, H4L, with Cu(OAc)(2)center dot H2O under acidic hydrothermal conditions (50:1 H2O/HNO3; 160 degrees C) led to the formation of crystalline {[Cu(HL')(H2O)]center dot H2O}, 1, which was structurally characterised to identify H3L' as 4,4',6-tricarboxy-2,2'-bipyridine. Clearly, in situ mono-decarboxylation of a tetracarboxylic acid ligand gave the tricarboxy-analogue, H3L'. The structure of 1 consists of a 1D coordination polymer that cross-links through hydrogen-bonding between adjacent carboxylic acid and carboxylate groups, as well as through an aqua ligand and lattice water molecule, to form a densely interconnected 3D network. Regioselective mono-decarboxylation of L or H4L at the 6'-carboxylic acid position may also be affected by heating L or H4L in acidic solution under hydrothermal conditions (2:1 H2O/HNO3; 160 degrees C) to yield crystalline 4,4',6'-tricarboxy-2,2'-bipyridinium nitrate hydrate {[H4L'][NO3]center dot H2O}, 2, which was also structural characterised. The structure of 2 features an array of hydrogen-bonding interactions that generate a 3D network. More forceful heating of the acidic solution at 180 degrees C led to double decarboxylation and the formation of 4,4'-dicarboxy-2,2'-bipyridine, whereas heating at 200 degrees C led to total decarboxylation and the formation of 2,2'-bipyridine. Details of the structures of 1 and 2 along with their synthesis are discussed. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.12.033
• 作为产物：
  描述：

  2,4-二甲基吡啶 在 palladium on activated charcoal 作用下， 生成 4,4',6,6'-四甲基-2,2'-联吡啶
  参考文献：
  名称：

  含甲基化联吡啶基型配体的Ru（II）同型和异型配合物的光化学和光生物学活性

  摘要：

  由于可以在空间和时间上控制生物效应，因此光活化化合物是用于医疗应用的强大工具和潜在试剂。钌多吡啶基配合物可以通过多种机制诱导细胞毒性作用，包括作为单线态氧的光敏剂（1 O 2）生产过程中，产生其他活性氧（ROS），释放生物活性配体，并形成与生物分子形成共价键的活性中间体。对一系列含有异构四甲基取代的联吡啶基型配体的Ru（II）配合物进行了结构-活性关系（SAR）研究。所研究的三个配体系统包含诱导应变的甲基基团，并创建了光不稳定的金属配合物，它们在光激活后可与生物分子形成共价键，而第四个不受约束并产生光稳定的配合物，可生成1 O 2。所研究的化合物包括含有两个联吡啶配体和第三个取代的配体的双杂配物和仅含有取代的配体的三均配体。评估了光物理，电化学，光化学和光生物学。发现应变杂合体复合物比三亲复合体具有更高的光活性和细胞毒性，并且联吡啶配体优于联嘧啶。然而，均检复合物表现出增强的抑制活细胞中蛋

  DOI：

  10.1021/acs.inorgchem.7b01642

文献信息

• Heteroleptic copper(<scp>i</scp>)–polypyridine complexes as efficient sensitizers for dye sensitized solar cells
  作者：Martina Sandroni、Ludovic Favereau、Aurelien Planchat、Huriye Akdas-Kilig、Nadine Szuwarski、Yann Pellegrin、Errol Blart、Hubert Le Bozec、Mohammed Boujtita、Fabrice Odobel

  DOI：10.1039/c4ta01755b

  日期：——

  Record photoconversion efficiency was achieved in DSC with stable heteroleptic bisdiimine complexes prepared by HETPHEN strategy.

  在采用HETPHEN策略制备的稳定杂环双二亚胺配合物的DSC中实现了记录的光电转换效率。
• Synthesis, Linear, and Quadratic-Nonlinear Optical Properties of Octupolar<i>D</i>₃and<i>D</i>_2<i>d</i>Bipyridyl Metal Complexes
  作者：Olivier Maury、Lydie Viau、Katell Sénéchal、Brigitte Corre、Jean-Paul Guégan、Thierry Renouard、Isabelle Ledoux、Joseph Zyss、Hubert Le Bozec

  DOI：10.1002/chem.200400012

  日期：2004.9.20

  A series of D3 (Fe(II), Ru(II), Zn(II), Hg(II)) and D2d (Cu(I), Ag(I), Zn(II)) octupolar metal complexes featuring different functionalized bipyridyl ligands has been synthesized, and their thermal, linear (absorption and emission), and nonlinear optical (NLO) properties were determined. Their quadratic NLO susceptibilities were determined by harmonic light scattering at 1.91 microm, and the molecular

  一系列具有不同官能化联吡啶的D3（Fe（II），Ru（II），Zn（II），Hg（II））和D2d（Cu（I），Ag（I），Zn（II））八极金属络合物已经合成了配体，并确定了它们的热，线性（吸收和发射）和非线性光学（NLO）性质。它们的二次NLO磁化率由1.91微米的谐波光散射确定，分子的超极化率（beta0）值在200-657 x 10（-30）esu范围内对于八面体络合物和70-157 x 10（-30） esu用于四面体配合物。八面体锌（II）配合物1 e包含4,4'-低聚亚苯基亚乙烯基官能化的2,2'-联吡啶，对于八极衍生物（lambdamax = 482 nm，beta1.91（1 e）= 870 x 10（-30）esu，beta0（1 e）= 657 x 10（-30）esu）。在本文中，我们证明了光学和非线性光学（NLO）特性受配合物的对称性，配体的性质（供体端基和pi连
• Spectrofluorometric method and compounds that are of value for the method
  申请人：Wallac Oy

  公开号：US05216134A1

  公开（公告）日：1993-06-01

  A chelate formed between Eu.sup.3+, Tb.sup.3+, Dy.sup.3+ and Sm.sup.3+ and a compound having the formula ##STR1## where A.sub.1-6 are single carbon or nitrogen atoms; n=1 or 2; R.sub.1-6 is nothing when A is a nitrogen, and hydrogen or an organic group when A is a carbon; Z and Z' are selected among --N(CH.sub.2 CH.sub.2 COO.sup.-).sub.2, --N(CH.sub.2 COO.sup.-).sub.2, --N(CH.sub.2 OPO.sub.3.sup.2-).sub.2 and --N(CH.sub.2 PO.sub.3.sup.2-).sub.2 ;--species that --X--Y is a substituent replacing a hydrogen anywhere in the parent compound; and --X--Y represents an organic group containing no chelating heteroatom closer than four atoms from a chelating heteroatom in the parent compound and X is a stable bridge containing certain groups and Y is selected from (a) specified relative groups allowing coupling to other compounds and (b) residues of compounds participating in biospecific affinity reactions.

  Eu.sup.3+、Tb.sup.3+、Dy.sup.3+和Sm.sup.3+之间形成的螯合物以及具有以下化学式的化合物：##STR1## 其中A.sub.1-6为单个碳或氮原子；n=1或2；当A为氮时，R.sub.1-6为无，当A为碳时为氢或有机基团；Z和Z'在--N(CH.sub.2 CH.sub.2 COO.sup.-).sub.2、--N(CH.sub.2 COO.sup.-).sub.2、--N(CH.sub.2 OPO.sub.3.sup.2-).sub.2和--N(CH.sub.2 PO.sub.3.sup.2-).sub.2中选择；--物种，其中--X--Y是替代父化合物中任何位置的氢的取代基；--X--Y代表含有没有比父化合物中的螯合异原子更近的螯合异原子的有机基团，X是包含特定基团的稳定桥，Y从(a)允许与其他化合物耦合的指定相对基团和(b)参与生物特异性亲和反应的化合物残基中选择。
• New 2,2?-Bipyridine Derivatives and Their Luminescence Properties with Europium(III) and Terbium(III) Ions
  作者：Veli-Matti Mukkala、Jouko J. Kankare

  DOI：10.1002/hlca.19920750512

  日期：1992.8.13

  Twenty differently substituted 2,2′,2″,2‴ -[(2,2′-bipyridine-6,6′-diyl)bis(methylenenitrilo)]tetrakis(acetc acids) 75–94 were synthesized with the purpose of developing new markers to be used in bioaffinity assays based on the unique luminescence properties of EuIII and TbIII ions. The relative luminescence yields, excitation maxima, and emission decay constants were determined for the corresponding

  合成了二十种不同取代的2,2'，2''，2‴-[（2,2'-联吡啶-6,6'-二基）双（亚甲基腈）]四（乙酸）75-94，用于开发基于Eu III和Tb III离子独特的发光特性，用于生物亲和力测定的新标记。确定了相应的Eu III和Tb III螯合物的相对发光产率，激发最大值和发射衰减常数。在联吡啶基的取代基对发光性能的效果显著：最好相对发光率ř用于与给电子取代基的配体，获得（例如Me，Ph），吸电子取代基（例如NO 2，COOH）具有相反的作用。然而，在相对发光产率和取代基参数之间没有发现明显的相关性。
• Reactions of substituted pyridines with electrophilic boranes
  作者：Christopher B. Caputo、Stephen J. Geier、Daniel Winkelhaus、Norbert W. Mitzel、V. Nicolas Vukotic、Stephen J. Loeb、Douglas W. Stephan

  DOI：10.1039/c1dt11820j

  日期：——

  The lutidine derivative (2,6-Me2)(4-Bpin)C5H2N when combined with B(C6F5)3 yields a frustrated Lewis pair (FLP) which reacts with H2 to give the salt [(2,6-Me2)(4-Bpin)C5H2NH][HB(C6F5)3] (1). Similarly 2,2′-(C5H2(4,6-Me2)N)2 and (4,4′-(C5H2(4,6-Me2)N)2 were also combined with B(C6F5)3 and exposed to H2 to give [(2,2′-HN(2,6-Me2)C5H2C5H2(4,6-Me2)N][HB(C6F5)3] (2) and [(4,4′-HN(2,6-Me2)C5H2C5H2(2,6-Me2)N]

  当与B（C 6 F 5）3结合时，二甲基吡啶衍生物（2,6-Me 2）（4-Bpin）C 5 H 2 N产生沮丧的Lewis对（FLP），其与H 2反应生成盐[ （2，6-Me 2）（4-Bpin）C 5 H 2 NH] [HB（C 6 F 5）3 ]（1）。类似地，2,2'-（C 5 H 2（4,6-Me 2）N）2和（4,4'-（C 5 H 2（4,6-Me 2）N）2也将其与B（C 6 F 5）3结合并暴露于H 2以获得[（2,2'-HN（2,6-Me 2）C 5 H 2 C 5 H 2（4,6-Me 2）N] [HB（C 6 F 5）3 ]（2）和[（4,4'-HN（2,6-Me 2）C 5 H 2 C 5 H 2（2,6-Me 2）N ] [HB（C 6 ˚F 5）3 ]（3），分别单-吡啶ñ-氧化物4,4'-N（2,6-Me 2）C 5 H 2 C 5 H 2（2,6-Me 2）NO形成加合物（4