5′-bromo-5-methyl-2,2′-bipyridine | 1187163-83-2

• 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: 5′-bromo-5-methyl-2,2′-bipyridine
• 英文别名: 5'-bromo-5-methyl-2,2'-bipyridine；5-bromo-5'-methyl-2,2'-bipyridine；5'-Bromo-5-methyl-[2,2']bipyridinyl；2-(5-bromopyridin-2-yl)-5-methylpyridine
• CAS: 1187163-83-2
• 化学式: C₁₁H₉BrN₂
• 分子量: 249.11
• InChiKey: LMIGNMKZAPNHIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5′-bromo-5-methyl-2,2′-bipyridine 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氯化碳 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 4,4′-bis[5″-(5‴-(2-formyl-4-tert-butylphenoxymethyl)-2″,2‴-bipyridinyl)]-1,1′-(2,2′,5,5′-tetramethoxy)biphenyl
  参考文献：
  名称：

  Post-Assembly Covalent Di- and Tetracapping of a Dinuclear [Fe₂L₃]⁴⁺ Triple Helicate and Two [Fe₄L₆]⁸⁺ Tetrahedra Using Sequential Reductive Aminations

  摘要：

  The use of a highly efficient reductive amination procedure for the postsynthetic end-capping of metal-templated helicate and tetrahedral supramolecular structures bearing terminal aldehyde groups is reported. Metal template formation of a [Fe2L3](4+) dinudear helicate and two [Fe4L6](8+) tetrahedra (where L is a linear ligand incorporating two bipyridine domains separated by one or two 1,4-(2,5-dimethoxyaryl) linkers and terminated by salicylaldehyde functions is described. Postassembly reaction of each of these "open" di- and tetranudear species with excess ammonium acetate (as a source of ammonia) and sodium cyanoborohydride results in a remarkable reaction sequence whereby the three aldehyde groups terminating each end of the helicate, or each of the four vertices of the respective tetrahedra, react with ammonia then undergo successive reductive amination to yield corresponding fully tertiary-amine capped cryptate and tetrahedral covalent cages.

  DOI：

  10.1021/acs.inorgchem.5b00940
• 作为产物：
  描述：

  5-METHYL-2-PYRIDYLZINC BROMIDE 、 5-溴-2-碘吡啶 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以63%的产率得到5′-bromo-5-methyl-2,2′-bipyridine
  参考文献：
  名称：

  2-吡啶基和3-吡啶基溴化锌：直接制备和偶联反应

  摘要：

  已证明使用Rieke锌分别与2-溴吡啶和3-溴吡啶直接合成2-吡啶基和3-吡啶基锌溴化物的简便合成方法。各种不同的亲电试剂已与所得的有机锌试剂偶联，以中等至良好的产率得到相应的交叉偶联产物。

  DOI：

  10.1016/j.tet.2010.02.061

文献信息

• 5-Ferrocenyl-2,2′-bipyridine ligands: synthesis, palladium(<scp>ii</scp>) and copper(<scp>i</scp>) complexes, optical and electrochemical properties
  作者：S. Ø. Scottwell、K. J. Shaffer、C. J. McAdam、J. D. Crowley

  DOI：10.1039/c4ra05333h

  日期：——

  Two 5-ferrocenyl-2,2′-bipyridine ligands were synthesised using the palladium(0) catalysed Suzuki–Miyaura cross-coupling reaction. Palladium(ii) and copper(i) complexes of these ligands were synthesised and the optical and electrochemical properties of the complexes were compared to those of the “free” ligands.

  两个5-二茂铁基-2,2′-联吡啶配体通过钯（0）催化的Suzuki–Miyaura交叉偶联反应合成。合成了这些配体的钯（ii）和铜（i）配合物，并将这些配合物的光学和电化学性质与“自由”配体进行了比较。
• New nickel(ii) and iron(ii) helicates and tetrahedra derived from expanded quaterpyridines
  作者：Christopher R. K. Glasson、George V. Meehan、Cherie A. Motti、Jack K. Clegg、Peter Turner、Paul Jensen、Leonard F. Lindoy

  DOI：10.1039/c1dt10667h

  日期：——

  of solvated [Ni2(2)3](PF6)4, [(PF6) ⊂ Fe4(2)6](PF6)7, [Fe4(3)6](PF6)8 and [Ni4(3)6](PF6)8 have been determined, while the structure of the parent Fe(II) cage in the series, [(PF6) ⊂ Fe4(1)6](PF6)7, was reported previously. The internal volumes of the Fe(II) tetrahedral cages have been calculated and increase from 102 Å3 for [Fe4(1)6]8+ to 227 Å3 for [Fe4(2)6]8+ to 417 Å3 for [Fe4(3)6]8+ and to an impressive

  作为涉及线性的先前研究的扩展 四吡啶配体，5,5''-二甲基-2,2'：5'，5'：2''，2'''-四吡啶1，相关的扩展四吡啶吡啶衍生物2和3的合成，并掺入了二甲氧基取代的成对的2,2'-联吡啶基之间的1,4-亚苯基和四甲氧基取代的4,4'-联亚苯基通过5-溴-5'-甲基-2'-联吡啶之间的双铃木偶联反应进行以及使用微波加热的适当的二频哪醇-二硼酸酯。的反应2和3与所选择的Fe（II）或Ni（II）盐产生既[M的混合物2大号3 ] 4+三螺旋体和[M 4 L 6 ] 8+四面体，在特定情况下，所形成的产物的比例取决于反应条件；各自的产品都具有足够的惰性，可以进行色谱分离和分离。发现更长的反应时间和更高的浓度有利于四面体的形成。[Ni 2（2）3 ]（PF 6）4，[（PF 6）⊂Fe 4（2）6 ]（PF 6）7，[Fe 4（3））6 ]（PF 6）8和[Ni 4（3）6 ]（PF 6）
• Cheap and Easy Synthesis of Highly Functionalized (Het)aryl Iodides via the Aromatic Finkelstein Reaction
  作者：Arne Lützen、Georg Meyer-Eppler、Lea Küchler、Christina Tenten、Christian Benkhäuser、Stefanie Brück

  DOI：10.1055/s-0033-1338598

  日期：——

  Aryl iodides are superior coupling partners in cross-coupling reactions compared to the corresponding chlorides or bromides. Unfortunately, the iodides are much more expensive, if commercially available at all, than the other halides. Thus, it is often mandatory to transform the available bromides into the corresponding iodides. The copper-catalyzed aromatic Finkelstein reaction turned out to be the method of choice to prepare a number of highly functionalized iodo(het)aryls, including pyridines, 2,2'-bipyridines, and chiral compounds.
• US9012344B2
  申请人：——

  公开号：US9012344B2

  公开（公告）日：2015-04-21
• 2-Pyridyl and 3-pyridylzinc bromides: direct preparation and coupling reaction
  作者：Seung-Hoi Kim、Reuben D. Rieke

  DOI：10.1016/j.tet.2010.02.061

  日期：2010.4

  A facile synthetic approach to the direct preparation of 2-pyridyl and 3-pyridylzinc bromides has been demonstrated using Rieke zinc with 2-bromopyridine and 3-bromopyridine, respectively. A variety of different electrophiles have been coupled with the resulting organozinc reagents to give the corresponding cross-coupling products in moderate to good yields.

  已证明使用Rieke锌分别与2-溴吡啶和3-溴吡啶直接合成2-吡啶基和3-吡啶基锌溴化物的简便合成方法。各种不同的亲电试剂已与所得的有机锌试剂偶联，以中等至良好的产率得到相应的交叉偶联产物。