2-(6-Pyridin-2-ylpyridin-2-yl)acetonitrile | 203573-77-7

• 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: 2-(6-Pyridin-2-ylpyridin-2-yl)acetonitrile
• CAS: 203573-77-7
• 化学式: C₁₂H₉N₃
• mdl: MFCD09923965
• 分子量: 195.224
• InChiKey: PIZCBJAYZRYJJE-UHFFFAOYSA-N

物化性质

• 沸点：
  364.4±32.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(6-Pyridin-2-ylpyridin-2-yl)acetonitrile 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以86%的产率得到2-([2,2'-Bipyridin]-6-yl)acetic acid
  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：

  6-氰基-2,2'-联吡啶 在 盐酸 、 sodium tetrahydroborate 、 氯化亚砜 、 硫酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 58.0h， 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

文献信息

• Regioselective Functionalization of 2,2'-Bipyridine and Transformations into Unsymmetric Ligands for Coordination Chemistry.
  作者：Thomas Norrby、Anna Börje、Lian Zhang、Björn Åkermark、John H. Wagenknecht、George W. Francis、József Szúnyog、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0077

  日期：——

  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.