N-甲基-2,2'-联吡啶-6-酮 | 154928-15-1

• 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: N-甲基-2,2'-联吡啶-6-酮
• 英文名称: 1-methyl-2,2'-bipyridine-6-one
• 英文别名: 1-methyl-1H-[2,2']bipyridinyl-6-one；1-methyl-[2,2'-bipyridin]-6(1H)-one；1-methyl-6-pyridin-2-ylpyridin-2-one
• CAS: 154928-15-1
• 化学式: C₁₁H₁₀N₂O
• mdl: MFCD26407592
• 分子量: 186.213
• InChiKey: IXPQFGHJFIWQLE-UHFFFAOYSA-N

物化性质

• 沸点：
  415.6±38.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 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：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-甲基-2,2'-联吡啶-6-酮 在 溴 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 29.0h， 生成 2-(6-Pyridin-2-ylpyridin-2-yl)acetonitrile
  参考文献：
  名称：

  Regioselective Functionalization of 2,2'-Bipyridine and Transformations into Unsymmetric Ligands for Coordination Chemistry.

  摘要：

  Novel synthetic strategies for a series of unsymmetrically substituted 2,2'-bipyridines have been developed. These bipyridines have found use in some novel homoleptic and heteroleptic ruthenium(II) complexes. Two methods for regiochemical control of nucleophilic addition to bpy have been explored: (i) mono N-oxidation followed by cyanation and subsequent hydrolysis gave 6-carboxy-2,2'-bipyridine (4); (ii) mono N-methylation followed by the conversion into 6-bromo-2,2'-bipyridine (12) and subsequent nucleophilic addition of lithio-acetonitrile followed by hydrolysis of 6-cyanomethyl-2,2'-bipyridine (8) gave the homologous 2,2'-bipyridine-6-acetic acid (9). An established method of regioselective mono-ring alkylation of bpy using methyllithium yielded 6-methyl-2,2'-bipyridine (14), and the generation of the anion of 14 and subsequent addition to a chloromethyl oxazoline was applied to synthesize a second homologue, methyl 2,2'-bipyridine-6-propanoate (16). Structural determinations using H-1, C-13 and 2D NMR spectroscopy permitted complete assignments of all signals in the H-1 NMR spectra.

  DOI：

  10.3891/acta.chem.scand.52-0077
• 作为产物：
  描述：

  1-甲基-2-(2-吡啶基)吡啶碘化物 在 potassium hexacyanoferrate(III) 、 sodium hydroxide 作用下， 以 水 为溶剂， 以77%的产率得到N-甲基-2,2'-联吡啶-6-酮
  参考文献：
  名称：

  Synthesis of new pyrrole–pyridine-based ligands using an in situ Suzuki coupling method

  摘要：

  化合物6-(吡咯-2-基)-2,2'-联吡啉，2-(吡咯-2-基)-1,10-邻菲啰啉和2-(2-(N-甲基苯并[d,e]咪唑)-6-(吡咯-2-基)-吡啉是通过使用原位生成的硼酸进行铃木偶联合成的。通过X射线分析可以生长出产物的晶体，并展示出有趣的结构，其中之一显示出链状网络，相邻分子通过分子间N–H^…N氢键相互连接。

  DOI：

  10.3762/bjoc.8.116

文献信息

• Synthesis of new pyrrole–pyridine-based ligands using an in situ Suzuki coupling method
  作者：Matthias Böttger、Björn Wiegmann、Steffen Schaumburg、Peter G Jones、Wolfgang Kowalsky、Hans-Hermann Johannes

  DOI：10.3762/bjoc.8.116

  日期：——

  The compounds 6-(pyrrol-2-yl)-2,2‘-bipyridine, 2-(pyrrol-2-yl)-1,10-phenanthroline and 2-(2-(N-methylbenz[d,e]imidazole)-6-(pyrrol-2-yl)-pyridine were synthesized by using an in situ generated boronic acid for the Suzuki coupling. Crystals of the products could be grown and exhibited interesting structures by X-ray analysis, one of them showing a chain-like network with the adjacent molecules linked to each other via intermolecular N–H^…N hydrogen bonds.

  化合物6-(吡咯-2-基)-2,2'-联吡啉，2-(吡咯-2-基)-1,10-邻菲啰啉和2-(2-(N-甲基苯并[d,e]咪唑)-6-(吡咯-2-基)-吡啉是通过使用原位生成的硼酸进行铃木偶联合成的。通过X射线分析可以生长出产物的晶体，并展示出有趣的结构，其中之一显示出链状网络，相邻分子通过分子间N–H^…N氢键相互连接。
• Syntheses and crystal structures of two self-assembled dizinc(II) helicates with novel hydrazone linked polypyridyl ligands
  作者：Hsien-Chang Kao、Yi-Chun Wang、Wen-Jwu Wang

  DOI：10.1007/s11164-016-2426-x

  日期：2017.6

  The rationally designed polydentate ligands, L 1 and L 2, based on the pyridinyl moiety and the hydrazone fragment have been synthesized to coordinate zinc(II) ions. We utilize pyridine as a rigid core connecting two bipyridines as ligand building blocks with a hydrozone linker for the L 1. The L 2 has a reversed design in which a bipyridine was used as a hinging-available building block of the ligand

  合成了基于吡啶基部分和the片段的合理设计的多齿配体L 1和L 2以配位锌（II）离子。我们利用吡啶作为刚性核心，将两个联吡啶作为配体构件与L 1的氢键连接。在大号 2具有相反的设计，其中一个联吡啶作为配体芯的铰接可用积木，具有腙连接体连接两个哒嗪臂。通过L 1和L 2的反应获得了两种新型的螺旋二锌（II）配合物用乙腈中的高氯酸锌（II）。两个螺旋结构的结构通过X射线衍射法确认。单链螺旋状Zn 2 L 1包含两个被氧原子桥接的锌离子。除了L 2配体，在双链螺旋状Zn 2 L 2 2中的两个锌离子之间没有发现其他桥联物质。通过紫外可见光谱滴定实验研究了溶液状态下螺旋状Zn 2 L 1的自组装过程。逐步形成常数暗示了螺旋产物的形成具有正性的协同行为。
• Field, John S.; Haines, Raymond J.; Parry, Campbell J., South African Journal of Chemistry, 1993, vol. 46, # 3/4, p. 70 - 74
  作者：Field, John S.、Haines, Raymond J.、Parry, Campbell J.、Sookraj, Sadesh H.

  DOI：——

  日期：——
• Field John S., Haines Raymond J., Parry Campbell J., Sookraj Sadesh H., S. Afr. J. Chem, 46 (1993) N 3-4, S 70-74
  作者：Field John S., Haines Raymond J., Parry Campbell J., Sookraj Sadesh H.

  DOI：——

  日期：——
• Synthesis and structures of two mononuclear iron(ii) complexes derived from polypyridine ligands
  作者：Hongqiao Wang、Nan Wu、Jing Zheng、Chunyang Zheng、Dunjia Wang

  DOI：10.1016/j.mencom.2020.01.033

  日期：2020.1

  Three polypyridine ligands such as tri(2-pyridyl)methane, (2,2’-bipyridin-6-yl)di(2-pyridyl)methane and 2,6-bis[di(2-pyridyl)methyl] pyridine as well as their new iron(II) mononuclear complexes have been obtained in a one-pot synthesis. Detailed structural analyses and magnetic susceptibility measurements confirm the expected six-coordinate octahedral geometry and the metric parameters are consistent

  三个聚吡啶配体，例如三（2-吡啶基）甲烷，（2,2'-联吡啶-6-基）二（2-吡啶基）甲烷和2,6-双[二（2-吡啶基）甲基]吡啶因为它们的新铁（II）单核络合物是通过一锅法合成获得的。详细的结构分析和磁化率测量结果证实了预期的六坐标八面体几何形状，并且度量参数与配合物中的低旋铁（II）一致。