ethyl 6-amino-5-cyano-2-ethoxy-4-(furan-2-yl)-2-(trifluoromethyl)-3,4-dihydro-2H-pyran-3-carboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 6-amino-5-cyano-2-ethoxy-4-(furan-2-yl)-2-(trifluoromethyl)-3,4-dihydro-2H-pyran-3-carboxylate
• 英文别名: Ethyl 6-amino-5-cyano-2-ethoxy-4-(furan-2-yl)-2-(trifluoromethyl)-3,4-dihydropyran-3-carboxylate；ethyl 6-amino-5-cyano-2-ethoxy-4-(furan-2-yl)-2-(trifluoromethyl)-3,4-dihydropyran-3-carboxylate
• 化学式: C₁₆H₁₇F₃N₂O₅
• 分子量: 374.317
• InChiKey: HTSPUEPPYBIBOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  乙醇 、 (2-呋喃亚甲基)丙二腈 、 三氟乙酰乙酸乙酯 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 50.0h， 以70%的产率得到ethyl 6-amino-5-cyano-2-ethoxy-4-(furan-2-yl)-2-(trifluoromethyl)-3,4-dihydro-2H-pyran-3-carboxylate
  参考文献：
  名称：

  Study on the reactions of ethyl 4,4,4-trifluoro-3-oxobutanoate with arylidenemalononitriles

  摘要：

  In the presence of a catalytic amount of NEt3, ethyl 4,4,4-trifluoro-3-oxobutanoate 1 reacted readily with arylidenemalononitriles 2 in ethanol at room temperature. It gave two products 2-trifluoromethyl-3,4-dihydro-2H-pyran derivatives 3 and 2-(trifluoromethyl)piperidine derivatives 4, the ratio of 3 and 4 was depended on the substrates 2 and reaction solvents. Reflux of the ethanol solution of 4 with a catalytic amount of NEt3 afforded 2-trifluoromethyl-1,4,5,6-tetrahydropyridine derivatives 5 in moderate to good yields. The structures of new compounds 3, 4 and 5 were determined by spectral methods, microanalysis and X-ray diffraction analysis. A possible reaction mechanism for the formation of 3, 4 and 5 was presented. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.039

文献信息

• Study on the reactions of ethyl 4,4,4-trifluoro-3-oxobutanoate with arylidenemalononitriles
  作者：Xianfu Li、Liping Song、Chunhui Xing、Jingwei Zhao、Shizheng Zhu

  DOI：10.1016/j.tet.2005.12.039

  日期：2006.3

  In the presence of a catalytic amount of NEt3, ethyl 4,4,4-trifluoro-3-oxobutanoate 1 reacted readily with arylidenemalononitriles 2 in ethanol at room temperature. It gave two products 2-trifluoromethyl-3,4-dihydro-2H-pyran derivatives 3 and 2-(trifluoromethyl)piperidine derivatives 4, the ratio of 3 and 4 was depended on the substrates 2 and reaction solvents. Reflux of the ethanol solution of 4 with a catalytic amount of NEt3 afforded 2-trifluoromethyl-1,4,5,6-tetrahydropyridine derivatives 5 in moderate to good yields. The structures of new compounds 3, 4 and 5 were determined by spectral methods, microanalysis and X-ray diffraction analysis. A possible reaction mechanism for the formation of 3, 4 and 5 was presented. (c) 2005 Elsevier Ltd. All rights reserved.