1,1'-(2,2'-联吡啶-6,6'-二基)二乙酮 | 49669-27-4

• 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: 1,1'-(2,2'-联吡啶-6,6'-二基)二乙酮
• 英文名称: 6,6'-diacetyl-2,2'-bipyridine
• 英文别名: 6,6’-diacetyl-2,2’-bipyridine；1,1'-([2,2'-bipyridine]-6,6'-diyl)bis(ethan-1-one)；1-[6-(6-acetylpyridin-2-yl)pyridin-2-yl]ethanone
• CAS: 49669-27-4
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: KYXBCPWHTPLSPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1'-(2,2'-联吡啶-6,6'-二基)二乙酮 在 potassium tert-butylate 、 ammonium acetate 、 溶剂黄146 作用下， 反应 50.0h， 生成 4',4''''''-bis(methylthio)-4'',4'''''-bis(n-porpylthio)-2,2':6',2'':6'',2''':6''',2'''':6'''',2''''':6''''',2'''''':6'''''',2'''''''-octipyridine
  参考文献：
  名称：

  Metal ion-induced self-assembly of functionalized 2,6-oligopyridines. 1. Ligand design, synthesis, and characterization

  摘要：

  Synthetic sequences utilizing alpha-oxoketene dithioacetal and enolate chemistry have been developed for the preparation of new functionalized bipyridines, terpyridines, quaterpyridines, quinquepyridines, sexipyridines, septipyridines, octipyridines, novipyridines, and decipyridines. Obtained in moderate to good yields, these oligopyridines were characterized by analytical and spectral data and, for sexipyridine, by X-ray crystallography.

  DOI：

  10.1021/ja00060a029
• 作为产物：
  描述：

  2,6-二溴吡啶 在 四(三苯基膦)钯 正丁基锂 作用下， 以 乙二醇二甲醚 、 乙醚 、 正己烷 为溶剂， 反应 114.0h， 生成 1,1'-(2,2'-联吡啶-6,6'-二基)二乙酮
  参考文献：
  名称：

  Synthetic Approaches to Polypyridyl Bridging Ligands with Proximal Multidentate Binding Sites

  摘要：

  A series of 12 bridging ligands was prepared. These ligands include a central linker appended to two 1,8-naphthyrid-2-yl or two 1,10-phenanthrolin-2-yl units. The linkers include pyridazin-3.6-diyl, 1,8-naphthyrid-2,7-diyl, 2,2'-bipyrid-6,6'-diyl, 1, 10-phenanthrolin-2,9-diyl, 1,2-di(2'-pyrid-6'-yl)ethyne, and 3,6-di(2'-pyrid-6'-yl)pyridazine. The ligands were synthesized from the diacetyl derivative of the central linker by a Friedlander condensation with either 2-aminonicotinaldehyde or 8-amino-7-quinolinecarbaldehyde. The precursor diacetyl derivatives were, in turn, prepared by pathways involving Stille and Sonogashira couplings. Examination of the electronic absorption spectra of the bridging ligands shows the strongest correlation to be between pairs of ligands having the same central linker. Complexation studies will follow.

  DOI：

  10.1021/jo051937r

文献信息

• Manganese-Catalyzed Hydroboration of Terminal Olefins and Metal-Dependent Selectivity in Internal Olefin Isomerization–Hydroboration
  作者：Subhash Garhwal、Asja A. Kroeger、Ranjeesh Thenarukandiyil、Natalia Fridman、Amir Karton、Graham de Ruiter

  DOI：10.1021/acs.inorgchem.0c03451

  日期：2021.1.4

  In the past decade, the use of earth-abundant metals in homogeneous catalysis has flourished. In particular, metals such as cobalt and iron have been used extensively in reductive transformations including hydrogenation, hydroboration, and hydrosilylation. Manganese, on the other hand, has been considerably less explored in these reductive transformations. Here, we report a well-defined manganese complex

  在过去的十年中，在均相催化中使用了富含地球的金属。特别地，诸如钴和铁的金属已广泛用于包括氢化，硼氢化和氢化硅烷化的还原转化中。另一方面，在这些还原性转变中对锰的研究较少。在这里，我们报告了一种定义明确的锰络合物[Mn（i Pr BDI）（OTf）2 ]（2a; BDI =联吡啶二胺），是多种电子分化烯烃的硼氢化反应中的活性预催化剂（> 20个实例）。加氢硼化对末端烯烃具有特别的选择性，并且具有排他的反马尔科夫尼科夫选择性。相反，当使用类似的钴络合物[Co（i Pr BDI）（OTf）2 ]（3a）时，内部烯烃被高效硼氢化，其中一系列异构化步骤最终导致其硼氢化。通过计算研究了锰和钴的对比末端烯烃对内部烯烃的选择性，并在本文报告的研究中作了进一步讨论。
• HETEROCYCLIC COMPOUND, AND ORGANIC LIGHT-EMITTING DEVICE USING SAME
  申请人：HEESUNG MATERIAL LTD.

  公开号：US20190233398A1

  公开（公告）日：2019-08-01

  The present application provides a hetero-cyclic compound capable of significantly enhancing lifespan, efficiency, electrochemical stability and thermal stability of an organic light emitting device, and an organic light emitting device containing the hetero-cyclic compound in an organic compound layer.

  本申请提供了一种杂环化合物，能够显著提高有机发光器件的寿命、效率、电化学稳定性和热稳定性，并且包含该杂环化合物在有机化合物层中的有机发光器件。
• Solid and solution state flexibility of sterically congested bis(imino)bipyridine complexes of zinc(<scp>ii</scp>) and nickel(<scp>ii</scp>)
  作者：Gerry A. Griffith、Mohamed J. Al-Khatib、Kalpana Patel、Kuldip Singh、Gregory A. Solan

  DOI：10.1039/b811309b

  日期：——

  Two new sterically demanding bis(imino)bipyridine ligands, 6,6'-(2,6-i-Pr(2)C(6)H(3))N=R}(2)C(10)H(6)N(2) (R = H (L1), Me (L2)), have been prepared in high yield by the condensation reaction of 2,6-diisopropylaniline with 6,6'-(O=R)(2)C(10)H(6)N(2) (R = H, Me). Palladium(0)-mediated cross coupling of 2-(Bu(3)Sn)-6-C(Me)OCH(2)CH(2)O}C(5)H(3)N with 2-Br-6-C(Me)OCH(2)CH(2)O}C(5)H(3)N, followed by an

  两个新的空间要求的双（亚氨基）双吡啶配体，6,6'-（2,6-i-Pr（2）C（6）H（3））N = R}（2）C（10）H（通过2,6-二异丙基苯胺与6,6'-（O = R）（2）的缩合反应高产率地制备了6）N（2）（R = H（L1），Me（L2）） C（10）H（6）N（2）（R = H，Me）。2-（Bu（3）Sn）-6- C（Me）OCH（2）CH（2）O} C（5）H（3）N与2-Br-的钯（0）介导的交叉偶联6- C（Me）OCH（2）CH（2）O} C（5）H（3）N，然后进行酸介导的脱保护作用，已被用作制备前体6,6'-的有效途径双（乙酰基）-2,2'-联吡啶。Aldimino L1与两个当量的MX（2）[MX（2）= ZnCl（2），NiCl（2）或（DME）NiBr（2）]在n-BuOH中在高温下反应，得到五坐标的单核络合物[（L1）MX（2）]（M = Zn，X
• Vinylation of Aldehydes Using Mn/Cr Alloy and a N₄-Ligand/Ni^II-Catalyst
  作者：Wacharee Harnying、Albrecht Berkessel

  DOI：10.1002/chem.201500024

  日期：2015.4.13

  We report an efficient and practical protocol for the Cr/Ni‐catalyzed vinylation of aldehydes, based on the use of Mn/Cr alloy (ca. 10 % Cr) and TMSCl. No additional Cr salts need to be added. In the presence of NiCl2 (0.3 mol %) and a bis(ketimino)‐2,2′‐bipyridine as N4‐chelating ligand (1 mol %), the vinylations proceed smoothly at room temperature. The presence of catalytic amounts of MeOH and LiOAc

  我们报告了基于Mn / Cr合金（约10％Cr）和TMSCl的Cr / Ni催化醛的乙烯基化的有效且实用的协议。无需添加其他铬盐。在存在NiCl 2（0.3 mol％）和作为N 4螯合配体的双（ketimino）-2,2'-联吡啶（1 mol％）的情况下，室温下乙烯基化反应顺利进行。发现即使没有配位体，催化量的MeOH和LiOAc作为添加剂的存在也可进一步提高催化体系的效率。详细的反应监测表明，LiOAc会加速产物醇的甲硅烷基化，从而提高周转率。
• Triazolopyridines. 18. Nucleophilic substitution reactions on triazolopyridines; a new route to 2,2′-bipyridines
  作者：Gurnos Jones、Mark A. Pitman、Edward Lunt、David J. Lythgoe、Belén Abarca、Rafael Ballesteros、Mostafá Elmasnaouy

  DOI：10.1016/s0040-4020(97)00491-2

  日期：1997.6

  The synthesis of some 5-, 6-, and 7-halogenotriazolopyridines is described, and their reactions with nucleophiles. The formation of 7,7′-bitriazolopyridines provides a new synthesis of 2,2′-bipyridines.

  描述了一些5-，6-和7-卤代三唑并吡啶的合成，以及它们与亲核试剂的反应。7,7'-双氮杂吡啶吡啶的形成提供了2,2'-联吡啶的新合成。