2-benzoylisonicotinonitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzoylisonicotinonitrile
• 英文别名: 2-benzoyl-4-cyanopyridine；2-Benzoylpyridine-4-carbonitrile
• 化学式: C₁₃H₈N₂O
• 分子量: 208.219
• InChiKey: MJAYULYNGFUDNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氰基吡啶 、 苯甲酰甲酸 在 NH₄S₂O₈ 、 硫酸 、 silver nitrate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.5h， 以100%的产率得到2-benzoylisonicotinonitrile
  参考文献：
  名称：

  Homolytic acylation of protonated pyridines and pyrazines with .alpha.-keto acids: the problem of monoacylation

  摘要：

  The silver-catalyzed decarboxylation of alpha-keto acids by persulfate leads to acyl radicals, which can effect the selective homolytic acylation of pyridine and pyrazine derivatives. Compared with the previously developed source of acyl radicals by hydrogen abstraction from aldehydes, this procedure is more effective in monoacylation when multiple positions of high nucleophilic reactivity are available in the heterocyclic ring. Although the introduction of an acyl group strongly activates the heterocyclic ring toward further substitution, monoacylation can be achieved by taking advantage of the difference in basicity and lipophilicity between the starting base and the monoacylation products in a two-phase system.

  DOI：

  10.1021/jo00008a050

文献信息

• Room Temperature Metal-Catalyzed Oxidative Acylation of Electron-Deficient Heteroarenes with Alkynes, Its Mechanism, and Application Studies
  作者：Shweta Sharma、Mukesh Kumar、Ram A. Vishwakarma、Mahendra K. Verma、Parvinder Pal Singh

  DOI：10.1021/acs.joc.8b01475

  日期：2018.10.19

  room-temperature, regioselective Minisci reaction for the acylation of electron-deficient heteroarenes with alkynes. The method has broad functional group compatibility and gives exclusively monoacylated products in good to excellent yields. The mechanistic pathway was analyzed based on a series of experiments confirming the involvement of a radical pathway. The 18O-labeling experiment suggested that water

  在这里，我们报告原始的一步式，简单的，室温，区域选择性Minisci反应，用于炔烃与缺电子的杂芳烃的酰化反应。该方法具有广泛的官能团相容性，并以良好至极佳的收率提供仅单酰化的产物。基于一系列实验证实了自由基途径的参与，对机械途径进行了分析。的18 O型标记实验表明，水是氧在酰化产物的源极，和头部空间GC-MS实验表明通过释放发生的C-C切割为CO 2。
• Visible-Light-Mediated Direct Decarboxylative Acylation of Electron-Deficient Heteroarenes Using α-Ketoacids
  作者：Sabyasachi Manna、Kandikere Ramaiah Prabhu

  DOI：10.1021/acs.joc.9b00004

  日期：2019.5.3

  Acylation of electron-deficient heteroaromatic compounds has been developed using visible light. α-Ketoacids have been used as an efficient source of acyl radicals under photoredox conditions. The in situ generated acyl radicals from α-ketoacids have been coupled to a wide variety of electron-deficient heteroaromatic compounds in a Minisci type reaction. This method would be attractive to access biologically

  利用可见光已经开发出了缺电子的杂芳族化合物的酰化剂。在光氧化还原条件下，α-酮酸已被用作酰基的有效来源。在Minisci型反应中，由α-酮酸原位生成的酰基已与多种电子不足的杂芳族化合物偶联。该方法对于获得生物学上有吸引力的分子将是有吸引力的。
• Polar effects in free-radical reactions. A novel homolytic acylation of heteroaromatic bases by aerobic oxidation of aldehydes, catalysed by<i>N</i>-hydroxyphthalimide and Co salts
  作者：Francesco Minisci、Francesco Recupero、Andrea Cecchetto、Carlo Punta、Cristian Gambarotti、Francesca Fontana、Gian Franco Pedulli

  DOI：10.1002/jhet.5570400220

  日期：2003.3

  A new process for the homolytic acylation of protonated heteroaromatic bases is described; an N-oxyl radical (PINO) generated from N-hydroxyphthalimide by air oxygen and Co(II) abstracts a hydrogen atom from an aldehyde. The resulting nucleophilic acyl radical adds to a heteroaromatic base, which is then rearo-matised in a chain process. Quinazoline has an anomalous behaviour, giving 3H-quinazolin-4-one

  描述了质子化杂芳族碱均质酰化的新方法。N-羟基邻苯二甲酰亚胺通过空气氧和Co（II）生成的N-氧基自由基（PINO）从醛中提取氢原子。所得的亲核酰基基团加到杂芳族碱基上，然后在链状过程中重新构型。喹唑啉具有异常行为，给出3 H-喹唑啉-4- 1是唯一的反应产物。
• Photoinduced Divergent Alkylation/Acylation of Pyridine <i>N</i>-Oxides with Alkynes under Anaerobic and Aerobic Conditions
  作者：Jin-hui Xu、Wen-bin Wu、Jie Wu

  DOI：10.1021/acs.orglett.9b01940

  日期：2019.7.5

  Ortho-alkylated and ortho-acylated pyridines have been conveniently synthesized from pyridine N-oxides and alkynes under visible-light-mediation in a metal-free manner. The alkynes served as both alkylating and acylating agents via switching between anaerobic and aerobic conditions. The overall strategy accommodates a broad scope of substituted pyridine N-oxides and alkynes, with excellent regioselectivity

  已经在可见光-介导下以无金属的方式方便地由吡啶N-氧化物和炔烃合成了邻烷基化和邻酰基化的吡啶。炔通过在厌氧和需氧条件之间切换而同时充当烷基化剂和酰化剂。总体策略适用于广泛范围的取代吡啶N-氧化物和炔烃，在许多情况下具有出色的区域选择性。
• FONTANA, FRANCESCA;MINISCI, FRANCESCO;BARBOSA, MARIA CLAUDIA NOGUEIRA;VIS+, J. ORG. CHEM., 56,(1991) N, C. 2866-2869
  作者：FONTANA, FRANCESCA、MINISCI, FRANCESCO、BARBOSA, MARIA CLAUDIA NOGUEIRA、VIS+

  DOI：——

  日期：——