4-cyano-N-(pyridin-2-yl)benzamide | 1017049-81-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-cyano-N-(pyridin-2-yl)benzamide
• 英文别名: 4-cyano-N-pyridin-2-ylbenzamide
• CAS: 1017049-81-8
• 化学式: C₁₃H₉N₃O
• mdl: MFCD09948594
• 分子量: 223.234
• InChiKey: IPJCZELLWRWAJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  348.2±22.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 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：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  哌啶 、 4-cyano-N-(pyridin-2-yl)benzamide 在 四氯化钛 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Toward versatile methods leading to highly functionalized imidazo[1,2-a]pyridines

  摘要：

  A convenient and general method of preparation of polyfunctionalized imidazo[1,2-a]pyridines is reported. This methodology involves activation of secondary amides leading to the formation of the corresponding amidines 9. Different activating reagents have been evaluated and the efficiency of PCl5 was illustrated with alkyl functionalized groups. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.117
• 作为产物：
  描述：

  在 四羟基二硼 作用下， 反应 0.17h， 以89 mg的产率得到4-cyano-N-(pyridin-2-yl)benzamide
  参考文献：
  名称：

  Rapid and Selective in situ Reduction of Pyridine-N-oxides with Tetra­hydroxydiboron

  摘要：

  Pyridine-N-oxides are often used as reactive precursors in the syntheses of substituted pyridines. Isolation and subsequent reduction of the associated pyridine-N-oxide intermediates can be challenging. We have discovered that tetrahydroxydiboron functions as a mild, versatile, and remarkably selective reducing agent for pyridine-N-oxides and may be used in an in situ fashion, thus obviating the isolation of N-oxide-containing intermediates

  DOI：

  10.1055/s-0033-1340010

文献信息

• Metal-Free Synthesis of <i>N</i>-(Pyridine-2-yl)amides from Ketones via Selective Oxidative Cleavage of C(O)–C(Alkyl) Bond in Water
  作者：Yanpeng Liu、Honghao Sun、Zhangjian Huang、Cong Ma、Aijun Lin、Hequan Yao、Jinyi Xu、Shengtao Xu

  DOI：10.1021/acs.joc.8b01956

  日期：2018.12.7

  N-(pyridine-2-yl)amides in water from ketones and 2-aminopyridine via direct oxidative C–C bond cleavage has been developed. A series of ketones, including more challenging inactive aromatic ketones substituted with diverse long-chain alkyl groups, were selectively converted to N-(pyridine-2-yl)amides. Furthermore, the protocol can be applied to aryl alkyl carbinols to afford the corresponding amides in moderate

  已经开发了TBHP / TBAI介导的通过直接氧化CC键从酮和2-氨基吡啶合成水中N-（吡啶-2-基）酰胺的方法。一系列酮，包括被各种长链烷基取代的更具挑战性的惰性芳族酮，被选择性地转化为N-（吡啶-2-基）酰胺。此外，该方案可以应用于芳基烷基甲醇，以中等至良好的产率得到相应的酰胺。
• A One-Pot Copper Catalyzed Biomimetic Route to <i>N</i>-Heterocyclic Amides from Methyl Ketones via Oxidative C–C Bond Cleavage
  作者：Parthasarathi Subramanian、Satrajit Indu、Krishna P. Kaliappan

  DOI：10.1021/ol5031266

  日期：2014.12.5

  A direct one-pot Cu-catalyzed biomimetic oxidation of methyl ketones to pharmaceutically important N-heterocyclic amides is reported. The scope of the method is broad, scalable, and mild, and the reaction is tolerant with various acid, base sensitive functionalities with multiple heteroatoms and aryl halides. The extensive mechanistic studies suggest that this reaction follows the Luciferin-Luciferase-like

  据报道，直接一锅铜催化的甲基酮仿生氧化成药学上重要的N-杂环酰胺。该方法的范围广泛，可扩展且温和，并且该反应可耐受具有多种杂原子和芳基卤化物的各种酸，碱敏感性官能团。广泛的机理研究表明，该反应遵循荧光素-荧光素酶样途径。
• Direct Transformation of Alkylarenes into <i>N</i> ‐(Pyridine‐2‐yl)amides by C(sp ³ )–C(sp ³ ) Bond Cleavage
  作者：Haipin Zhou、Yanpeng Liu、Haidong Xia、Jinyi Xu、Tingfang Wang、Shengtao Xu

  DOI：10.1002/ejoc.202001137

  日期：2020.11.8

  A mild and green methodology for the construction of N‐(pyridine‐2‐yl)amides from alkylarenes and 2‐aminopyridine in one step was developed. Various alkylarenes were directly transformed into the corresponding N‐(pyridine‐2‐yl)amides through tandem C(sp3)–H bond activation/oxidative cyclization/C–C bond cleavage.

  开发了一种温和且绿色的方法，可一步一步从烷基芳烃和2-氨基吡啶构建N-（吡啶-2-基）酰胺。通过串联C（sp 3）-H键活化/氧化环化/ CC键断裂，各种烷基芳烃直接转化为相应的N-（吡啶-2-基）酰胺。
• Microwave-assisted heteropolyanion-based ionic liquid promoted sustainable protocol to N-heteroaryl amides via N-directing dual catalyzed oxidative amidation of aldehydes
  作者：Renzhong Fu、Yang Yang、Weihua Jin、Hui Gu、Xiaojun Zeng、Wen Chai、Yunsheng Ma、Quan Wang、Jun Yi、Rongxin Yuan

  DOI：10.1039/c6ra20961k

  日期：——

  A procedure for the synthesis of N-heteroaryl amides directly from oxidative amidation of aldehydes catalyzed by heteropolyanion-based ionic liquids has been reported. The proposed N-directing dual-catalysis mechanism was briefly investigated.

  报告了一种在杂多阴离子基离子液体催化下直接从醛的氧化酰胺化反应合成 N-杂芳基酰胺的方法。对所提出的 N-定向双催化机理进行了简要研究。
• A facile tandem decyanation/cyanation reaction of α-iminonitriles toward cyano-substituted amides
  作者：Zhengwang Chen、Pei Liang、Botao Liu、Haiqing Luo、Jing Zheng、Xiaowei Wen、Tanggao Liu、Min Ye

  DOI：10.1039/c8ob02186d

  日期：——

  A new tandem decyanation/cyanation reaction of α-iminonitriles has been developed. A variety of cyano-substituted aryl amides and heteroaryl amides are synthesized in good yields. Both electron-rich and electron-deficient groups are compatible with the standard conditions. This reaction features a nonmetallic cyano source, tandem decyanation and cyanation reaction, waste utilization of the HCN from

  已经开发了一种新的α-亚胺的串联脱氰/氰化反应。以高收率合成了多种氰基取代的芳基酰胺和杂芳基酰胺。富电子和缺电子基团均符合标准条件。该反应具有非金属氰基来源，串联脱氰和氰化反应，α-亚氨基水解产生的HCN废物利用，一步操作形成两个重要的官能团等特点。