2-[2-acetyl-1-(2-nitrophenyl)-3-oxobutyl]-acrylonitrile | 910456-62-1

• 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: 2-[2-acetyl-1-(2-nitrophenyl)-3-oxobutyl]-acrylonitrile
• 英文别名: 4-Acetyl-2-methylidene-3-(2-nitrophenyl)-5-oxohexanenitrile；4-acetyl-2-methylidene-3-(2-nitrophenyl)-5-oxohexanenitrile
• CAS: 910456-62-1
• 化学式: C₁₅H₁₄N₂O₄
• 分子量: 286.287
• InChiKey: MYPNSIOQSOSTSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[2-acetyl-1-(2-nitrophenyl)-3-oxobutyl]-acrylonitrile 在 硫酸 、 三氟乙酸 作用下， 反应 0.08h， 以35%的产率得到5-acetyl-4-(2-nitrophenyl)-6-methyl-3-methylene-3,4-dihydropyridin-2(1H)-one
  参考文献：
  名称：

  Synthesis of substituted 3-methylene-2-pyridones from Baylis–Hillman derivatives and its application for the generation of 2-pyridone substituted spiroisoxazolines

  摘要：

  The synthesis of substituted 3-methylene-2-pyridones via S(N)2 displacement reaction of nucleophiles bearing a keto group on the acetyl derivative of Baylis-Hillman adducts of acrylonitrile followed by TFA/H2SO4-mediated intramolecular cyclization is described. The utility of these pyridone derivatives for the synthesis of new spiroisoxazolines in highly regio- and stereo-selective fashion is also illustrated. The structure of the spiroisoxazolines has been secured via X-ray crystallographic analysis. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.074
• 作为产物：
  描述：

  乙酰丙酮 、 2-[acetyloxymethyl(2-nitrophenyl)]acrylonitrile 在 三乙烯二胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.25h， 以65%的产率得到2-[2-acetyl-1-(2-nitrophenyl)-3-oxobutyl]-acrylonitrile
  参考文献：
  名称：

  Synthesis of substituted 3-methylene-2-pyridones from Baylis–Hillman derivatives and its application for the generation of 2-pyridone substituted spiroisoxazolines

  摘要：

  The synthesis of substituted 3-methylene-2-pyridones via S(N)2 displacement reaction of nucleophiles bearing a keto group on the acetyl derivative of Baylis-Hillman adducts of acrylonitrile followed by TFA/H2SO4-mediated intramolecular cyclization is described. The utility of these pyridone derivatives for the synthesis of new spiroisoxazolines in highly regio- and stereo-selective fashion is also illustrated. The structure of the spiroisoxazolines has been secured via X-ray crystallographic analysis. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.074

文献信息

• Synthesis of substituted 3-methylene-2-pyridones from Baylis–Hillman derivatives and its application for the generation of 2-pyridone substituted spiroisoxazolines
  作者：Virender Singh、Gaya P. Yadav、Prakas R. Maulik、Sanjay Batra

  DOI：10.1016/j.tet.2008.01.074

  日期：2008.3

  The synthesis of substituted 3-methylene-2-pyridones via S(N)2 displacement reaction of nucleophiles bearing a keto group on the acetyl derivative of Baylis-Hillman adducts of acrylonitrile followed by TFA/H2SO4-mediated intramolecular cyclization is described. The utility of these pyridone derivatives for the synthesis of new spiroisoxazolines in highly regio- and stereo-selective fashion is also illustrated. The structure of the spiroisoxazolines has been secured via X-ray crystallographic analysis. (C) 2008 Elsevier Ltd. All rights reserved.