ethyl (2E)-4,4,4-trifluoro-3-oxo-2-(pyridin-2-ylaminomethylidene)butanoate

• 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: ethyl (2E)-4,4,4-trifluoro-3-oxo-2-(pyridin-2-ylaminomethylidene)butanoate
• 英文别名: ethyl (2E)-4,4,4-trifluoro-3-oxo-2-[(pyridin-2-ylamino)methylidene]butanoate
• 化学式: C₁₂H₁₁F₃N₂O₃
• 分子量: 288.226
• InChiKey: ASWSIIVABQISPT-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  68.29
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 乙氧基-2-亚甲基三氟乙酰乙酸乙酯 以 乙醚 为溶剂， 反应 4.0h， 以56%的产率得到ethyl (2E)-4,4,4-trifluoro-3-oxo-2-(pyridin-2-ylaminomethylidene)butanoate
  参考文献：
  名称：

  Synthesis and structure of 2-ethoxy- and 2-aminomethylidene-3-fluoroalkyl-3-oxopropionates

  摘要：

  Condensation of ethyl 3-polyfluoroalkyl-3-oxopropionates with excess triethyl orthoformate gave ethyl 3-polyfluoroalkyl-2-ethoxymethylidene-3-oxopropionates which reacted with primary aliphatic, aromatic, and heterocyclic amines to form ethyl 2-alkyl(aryl, hetaryl)aminomethylidene-3-polyfluoroalkyl-3-oxopropionates. According to the X-ray diffraction and IR data, the latter exist in the crystalline state as the corresponding E isomers, while in solution (NMR data), as mixtures of Z and E isomers. Condensation of ethyl 2-ethoxymethylidene-3-oxopropionates with secondary heterocyclic amines (morpholine and pyrrolidine) led to the formation of 2-morpholino(pyrrolidin-1-yl)methylidene-3-fluoroalkyl-3-oxopropionates which were shown to exist as Z isomers both in the crystalline state and in solution.

  DOI：

  10.1134/s1070428007070019

文献信息

• Synthesis and structure of 2-ethoxy- and 2-aminomethylidene-3-fluoroalkyl-3-oxopropionates
  作者：M. V. Pryadeina、Ya. V. Burgart、V. I. Saloutin、P. A. Slepukhin、O. N. Kazheva、G. V. Shilov、O. A. D’yachenko、O. N. Chupakhin

  DOI：10.1134/s1070428007070019

  日期：2007.7

  Condensation of ethyl 3-polyfluoroalkyl-3-oxopropionates with excess triethyl orthoformate gave ethyl 3-polyfluoroalkyl-2-ethoxymethylidene-3-oxopropionates which reacted with primary aliphatic, aromatic, and heterocyclic amines to form ethyl 2-alkyl(aryl, hetaryl)aminomethylidene-3-polyfluoroalkyl-3-oxopropionates. According to the X-ray diffraction and IR data, the latter exist in the crystalline state as the corresponding E isomers, while in solution (NMR data), as mixtures of Z and E isomers. Condensation of ethyl 2-ethoxymethylidene-3-oxopropionates with secondary heterocyclic amines (morpholine and pyrrolidine) led to the formation of 2-morpholino(pyrrolidin-1-yl)methylidene-3-fluoroalkyl-3-oxopropionates which were shown to exist as Z isomers both in the crystalline state and in solution.