4-氰基-N-(6-甲基吡啶-2-基)苯甲酰胺 | 1019385-85-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氰基-N-(6-甲基吡啶-2-基)苯甲酰胺
• 英文名称: 4-cyano-N-(6-methylpyridin-2-yl)benzamide
• CAS: 1019385-85-3
• 化学式: C₁₄H₁₁N₃O
• mdl: MFCD10663417
• 分子量: 237.261
• InChiKey: AXSOUIICIQVSBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  132-134 °C
• 沸点：
  351.0±37.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基-6-甲基吡啶 在 四(三苯基膦)钯 、 potassium carbonate 、 cerium triflate 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 12.17h， 生成 4-氰基-N-(6-甲基吡啶-2-基)苯甲酰胺
  参考文献：
  名称：

  α-亚胺向氰基取代的酰胺的简便串联脱氰/氰化反应

  摘要：

  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。

  DOI：

  10.1039/c8ob02186d

文献信息

• Structure−Activity Relationships Comparing <i>N</i>-(6-Methylpyridin-yl)-Substituted Aryl Amides to 2-Methyl-6-(substituted-arylethynyl)pyridines or 2-Methyl-4-(substituted-arylethynyl)thiazoles as Novel Metabotropic Glutamate Receptor Subtype 5 Antagonists
  作者：Santosh S. Kulkarni、Mu-Fa Zou、Jianjing Cao、Jeffrey R. Deschamps、Alice L. Rodriguez、P. Jeffrey Conn、Amy Hauck Newman

  DOI：10.1021/jm900172f

  日期：2009.6.11

  The metabotropic glutamate receptor subtype 5 (mGluR5) has been implicated in anxiety, depression, pain, mental retardation, and addiction. The potent and selective noncompetitive mGluR5 antagonist 2-methyl-6-(phenylethynyl)pyridine (MPEP, 1) has been a critically important tool used to further elucidate the role of mGluR5 in these CNS disorders. In an effort to provide novel and structurally diverse selective mGluR5 antagonists, we previously described a set of analogues with moderate activity wherein the alkyne bond was replaced with an amide group. In the present report, extended series of both amide and alkyne-based ligands were synthesized. MGluR5 binding and functional data were obtained that identified (1) several novel alkynes with comparable affinities to 1 at mGluR5 (e.g., 10 and 20-23), but (2) most structural variations to the amide template were not well tolerated, although a few potent amides were discovered (e.g., 55 and 56). Several of these novel analogues show drug-like physical properties (e.g., cLogP range = 2-5) that support their use for in vivo investigation into the role of mGluR5 in CNS disorders.
• 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。