5-methyl-2-(pyridin-2-yl)isophthalonitrile | 1389329-43-4

• 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
• 英文名称: 5-methyl-2-(pyridin-2-yl)isophthalonitrile
• 英文别名: 5-Methyl-2-pyridin-2-ylbenzene-1,3-dicarbonitrile；5-methyl-2-pyridin-2-ylbenzene-1,3-dicarbonitrile
• CAS: 1389329-43-4
• 化学式: C₁₄H₉N₃
• 分子量: 219.246
• InChiKey: CLAKUIMJLIQAHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-甲基苯基)吡啶 、 N-氰基-4-甲基-N-苯基苯磺酰胺 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以74%的产率得到5-methyl-2-(pyridin-2-yl)benzonitrile
  参考文献：
  名称：

  Rhodium Catalyzed Cyanation of Chelation Assisted C–H Bonds

  摘要：

  A rhodium-catalyzed cyanation of chelation assisted C-H bonds is described employing N-cyano-N-phenyl-p-methylbenzenesulfonamide as an efficient cyanating reagent. The present method allowed the synthesis of various benzonitirle derivatives in good to excellent yield. A number of chelating groups are also effective in the present cyanation of C-H bonds. In addition, the developed methodology was applied in the formal synthesis of the isoquinoline alkaloid, menisporphine.

  DOI：

  10.1021/ol402201c

文献信息

• Copper-Catalyzed Aromatic CH Bond Cyanation by CCN Bond Cleavage of Inert Acetonitrile
  作者：Xuezhen Kou、Mengdi Zhao、Xixue Qiao、Yamin Zhu、Xiaofeng Tong、Zengming Shen

  DOI：10.1002/chem.201303637

  日期：2013.12.9

  Cut and paste! A Cu‐catalyzed aromatic CH cyanation with acetonitrile as the nitrile source by CCN cleavage has been developed (see scheme; TMEDA=N,N,N′,N′‐tetramethylethylenediamine). The reaction is catalytic in copper, and it is found that using (Me3Si)2 as an additive plays a critical role in promoting CCN cleavage and enhancing the reaction rate.

  剪切和粘贴！已开发出一种通过CCN裂解的乙腈为腈源的Cu催化的芳族CH氰化反应（参见方案； TMEDA = N，N，N ′，N′-四甲基乙二胺）。该反应在铜中是催化的，发现使用（Me 3 Si）2作为添加剂在促进CCN裂解和提高反应速率方面起着关键作用。
• Copper-Mediated Selective Cyanation of Indoles and 2-Phenylpyridines with Ammonium Iodide and DMF
  作者：Jinho Kim、Hyunwoo Kim、Sukbok Chang

  DOI：10.1021/ol301674m

  日期：2012.8.3

  Copper-mediated regioselective cyanation of indoles and 2-phenylpyridines was developed by using ammonium iodide and DMF as the combined source of a cyano unit under "Pd-free" conditions. Mechanistic studies indicate that the reaction of indoles proceeds through a two-step sequence: electrophilic initial iodination and then cyanation. The cyanation has a broad substrate scope, high functional group tolerance, and excellent regloselectivity.
• Rhodium Catalyzed Cyanation of Chelation Assisted C–H Bonds
  作者：Manthena Chaitanya、Dongari Yadagiri、Pazhamalai Anbarasan

  DOI：10.1021/ol402201c

  日期：2013.10.4

  A rhodium-catalyzed cyanation of chelation assisted C-H bonds is described employing N-cyano-N-phenyl-p-methylbenzenesulfonamide as an efficient cyanating reagent. The present method allowed the synthesis of various benzonitirle derivatives in good to excellent yield. A number of chelating groups are also effective in the present cyanation of C-H bonds. In addition, the developed methodology was applied in the formal synthesis of the isoquinoline alkaloid, menisporphine.