ethyl 1-[2-cyano-1-(4-methylphenyl)allyl]-2-oxocyclopentanecarboxylate | 1020667-34-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethyl 1-[2-cyano-1-(4-methylphenyl)allyl]-2-oxocyclopentanecarboxylate
• CAS: 1020667-34-8
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: NIFNOJOGNAQINR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  67.16
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 1-[2-cyano-1-(4-methylphenyl)allyl]-2-oxocyclopentanecarboxylate 在 硫酸 、 三氟乙酸 作用下， 反应 0.12h， 生成 cis-ethyl 3-methylene-2-oxo-4-(4-methylphenyl)-1,2,3,4,5,6-hexahydro-4aH-cyclopenta[b]pyridine-4a-carboxylate 、 cis-ethyl 3-methylene-2-oxo-4-(4-methylphenyl)-1,2,3,4,5,6-hexahydro-4aH-cyclopenta[b]pyridine-4a-carboxylate
  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-氧代环戊羧酸乙酯 、 Acetic acid 2-cyano-1-p-tolyl-allyl ester 在 三乙烯二胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.25h， 以78%的产率得到ethyl 1-[2-cyano-1-(4-methylphenyl)allyl]-2-oxocyclopentanecarboxylate
  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