5-acetyl-6-methyl-3-methylene-4-(4-methylphenyl)-3,4-dihydropyridin-2(1H)-one | 1020666-89-0

• 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: 5-acetyl-6-methyl-3-methylene-4-(4-methylphenyl)-3,4-dihydropyridin-2(1H)-one
• 英文别名: 5-Acetyl-6-methyl-3-methylidene-4-(4-methylphenyl)-1,4-dihydropyridin-2-one；5-acetyl-6-methyl-3-methylidene-4-(4-methylphenyl)-1,4-dihydropyridin-2-one
• CAS: 1020666-89-0
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: RTOHIIJJTBUFOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯甲腈 N-氧化物 、 5-acetyl-6-methyl-3-methylene-4-(4-methylphenyl)-3,4-dihydropyridin-2(1H)-one 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以82%的产率得到9-acetyl-8-methyl-10-(4-methylphenyl)-3-phenyl-1-oxa-2,7-diazaspiro[4.5]deca-2,8-dien-6-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：

  2-[2-acetyl-1-(4-methylphenyl)-3-oxobutyl]acrylonitrile 在 硫酸 、 三氟乙酸 作用下， 反应 0.08h， 以70%的产率得到5-acetyl-6-methyl-3-methylene-4-(4-methylphenyl)-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

文献信息

• Straightforward Strategy for the Stereoselective Synthesis of Spiro-Fused (C-5)Isoxazolino- or (C-3)Pyrazolino-(C-3)quinolin-2-ones from Baylis-Hillman Adducts by 1,3-Dipolar Cycloaddition and Reductive Cyclization
  作者：Virender Singh、Vijay Singh、Sanjay Batra

  DOI：10.1002/ejoc.200800746

  日期：2008.11

  A straightforward and general approach for the stereoselective synthesis of spiro-fused (C-5)isoxazolino- or (C-3)pyrazolino-(C-3)quinolin-2-ones from the adducts offorded from the Baylis–Hillman reaction of 2-nitrobenzaldehyde and ethyl acrylate by sequential 1,3-dipolar cycloaddition and reductive cyclization is presented. It was found that the reductive cyclization of the isoxazoline derivatives

  从 2 的 Baylis-Hillman 反应提供的加合物立体选择性合成螺稠合 (C-5)isoxazolino- 或 (C-3)pyrazolino-(C-3)quinolin-2-ones 的直接和通用方法-硝基苯甲醛和丙烯酸乙酯通过顺序 1,3-偶极环加成和还原环化反应。发现异恶唑啉衍生物的还原环化在 In/HCl 存在下有效进行，而吡唑啉的类似还原在 Fe/AcOH 混合物存在下进行时产生更好的产率。然而，使用 2-硝基苯甲醛和甲基乙烯基酮的 Baylis-Hillman 加合物的类似尝试没有产生所需的化合物。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2008 年）
• 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.