2-methyl-6-oxo-4-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile | 27036-92-6

• 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-methyl-6-oxo-4-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile
• 英文别名: 5-cyano-6-methyl-4-phenyl-3,4-dihydropyridin-2(1H)-one；3,4-dihydro-5-cyano-6-methyl-4-phenyl-2(1H)-pyridone；2-methyl-6-oxo-4-phenyl-1,4,5,6-tetrahydro-pyridine-3-carbonitrile；5-Cyano-1,2,3,4-tetrahydro-6-methyl-2-oxo-4-phenylpyridine；6-methyl-2-oxo-4-phenyl-3,4-dihydro-1H-pyridine-5-carbonitrile
• CAS: 27036-92-6
• 化学式: C₁₃H₁₂N₂O
• 分子量: 212.251
• InChiKey: VOWWGPXZMYRPNS-UHFFFAOYSA-N

物化性质

• 沸点：
  441.0±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-6-oxo-4-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile 在 劳森试剂 作用下， 以 苯 为溶剂， 反应 8.0h， 以87%的产率得到2-methyl-4-phenyl-6-thioxo-1,4,5,6-tetrahydropyridine-3-carbonitrile
  参考文献：
  名称：

  KO^tBu-mediated annulation of acetonitrile with aldehyde: synthesis of substituted dihydropyridin-2(1H)-ones, pyridin-2(1H)-ones, and thiopyridin-2(1H)-ones

  摘要：

  KO^tBu介导的乙腈与醛的环化反应观察到发生了四个C(sp³)–H键的断裂，并形成了总共八个新键。

  DOI：

  10.1039/c5cc02964c
• 作为产物：
  描述：

  2-methyl-4-phenyl-6-thioxo-1,4,5,6-tetrahydropyridine-3-carbonitrile 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 以90%的产率得到2-methyl-6-oxo-4-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile
  参考文献：
  名称：

  Dutta Chowdhury; Sarkar, Mili; Chatterjee, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 10, p. 2563 - 2566

  摘要：

  DOI：

文献信息

• Enantioselective Synthesis of Dihydropyridinones via NHC-Catalyzed Aza-Claisen Reaction
  作者：Benedikt Wanner、Jessada Mahatthananchai、Jeffrey W. Bode

  DOI：10.1021/ol202272t

  日期：2011.10.7

  N-Heterocyclic carbene catalyzed aza-Claisen annulations of enals or their alpha'-hydrozyenone surrogates with vinylogous amides afford dihydropyridinones. The reaction proceeds with a broad range of substrates, and no nitrogen protecting group is required.
• Dutta Chowdhury; Sarkar, Mili; Roy Chowdhury, Synthetic Communications, 1996, vol. 26, # 22, p. 4233 - 4251
  作者：Dutta Chowdhury、Sarkar, Mili、Roy Chowdhury、Mahalanabis, Kumar K.

  DOI：——

  日期：——
• Mahalanabis, Kumar K.; Sarkar, Mili; Dutta Chowdhury, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 12, p. 1234 - 1238
  作者：Mahalanabis, Kumar K.、Sarkar, Mili、Dutta Chowdhury、Dutta-Bose, Sharmila

  DOI：——

  日期：——
• Mahalanabis, Kumar K.; Mukherjee, Attreyee, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2021, vol. 60, # 2, p. 291 - 302
  作者：Mahalanabis, Kumar K.、Mukherjee, Attreyee

  DOI：——

  日期：——
• KO^tBu-mediated annulation of acetonitrile with aldehyde: synthesis of substituted dihydropyridin-2(1<i>H</i>)-ones, pyridin-2(<i>1H</i>)-ones, and thiopyridin-2(1<i>H</i>)-ones
  作者：Abhimanyu Yadav、Ajay Verma、Saket Patel、Amit Kumar、Vandana Rathore、Meenakshi、Shailesh Kumar、Sangit Kumar

  DOI：10.1039/c5cc02964c

  日期：——

  KO^tBu-mediated annulation of acetonitrile with aldehyde was observed in which cleavage of four C(sp³)–H bonds occurred, and total eight new bonds formed.

  KO^tBu介导的乙腈与醛的环化反应观察到发生了四个C(sp³)–H键的断裂，并形成了总共八个新键。

表征谱图