2-cyano-6-(trifluoromethyl)-4-pyrone | 1374032-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-cyano-6-(trifluoromethyl)-4-pyrone
• 英文别名: 2-cyano-6-(trifluoromethyl)-4H-pyran-4-one；4-Oxo-6-(trifluoromethyl)-4H-pyran-2-carbonitrile；4-oxo-6-(trifluoromethyl)pyran-2-carbonitrile
• CAS: 1374032-25-3
• 化学式: C₇H₂F₃NO₂
• 分子量: 189.094
• InChiKey: NJNYVPDVXTVWGV-UHFFFAOYSA-N

物化性质

• 沸点：
  208.0±40.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-cyano-6-(trifluoromethyl)-4-pyrone 在 甲烷磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 24.5h， 生成 N,1-dibutyl-4-oxo-6-(trifluoromethyl)pyridine-3-carboxamide
  参考文献：
  名称：

  A novel, two-step synthesis of 4-pyridone-3-carboxamides from 2-cyano-4-pyrones

  摘要：

  Reactions of 2-cyano-6-(trifluoromethyl)-4-pyrone, 2-cyano-4-pyrone, and 2-cyano-6-methyl-4-pyrone with aliphatic and aromatic amines in ethanol at -20 degrees C for 2-21 days gave 5-amino-3-oxopent-4-enamides in 28-78% yields, which were cyclized with DMF-DMA in toluene under ambient conditions to afford 4-pyridone-3-carboxamides in 31-70% yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.132
• 作为产物：
  描述：

  4-oxo-6-(trifluoromethyl)-4H-pyran-2-carboxamide 在 吡啶 、 三氟乙酸酐 作用下， 以61%的产率得到2-cyano-6-(trifluoromethyl)-4-pyrone
  参考文献：
  名称：

  A novel, two-step synthesis of 4-pyridone-3-carboxamides from 2-cyano-4-pyrones

  摘要：

  Reactions of 2-cyano-6-(trifluoromethyl)-4-pyrone, 2-cyano-4-pyrone, and 2-cyano-6-methyl-4-pyrone with aliphatic and aromatic amines in ethanol at -20 degrees C for 2-21 days gave 5-amino-3-oxopent-4-enamides in 28-78% yields, which were cyclized with DMF-DMA in toluene under ambient conditions to afford 4-pyridone-3-carboxamides in 31-70% yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.132

文献信息

• 2-Cyano-6-(trifluoromethyl)-4H-pyran-4-one: A novel versatile CF3-containing building block
  作者：Boris I. Usachev、Dmitrii L. Obydennov、Gerd-Volker Röschenthaler、Vyacheslav Ya. Sosnovskikh

  DOI：10.1016/j.jfluchem.2012.01.006

  日期：2012.5

  A highly electrophilic pyrone, 2-cyano-6-(trifluoromethyl)-4H-pyran-4-one, was synthesized. The reactions of this cyanopyrone with N-nucleophiles can proceed with or without substitution of the cyano group to give a wide range of novel trifluoromethylated compounds. An oxindole derivative was synthesized from a phenylhydrazide using unusual (acidic) conditions. (c) 2012 Elsevier B.V. All rights reserved.
• A novel, two-step synthesis of 4-pyridone-3-carboxamides from 2-cyano-4-pyrones
  作者：Dmitrii L. Obydennov、Ekaterina S. Sidorova、Boris I. Usachev、Vyacheslav Ya. Sosnovskikh

  DOI：10.1016/j.tetlet.2013.03.132

  日期：2013.6

  Reactions of 2-cyano-6-(trifluoromethyl)-4-pyrone, 2-cyano-4-pyrone, and 2-cyano-6-methyl-4-pyrone with aliphatic and aromatic amines in ethanol at -20 degrees C for 2-21 days gave 5-amino-3-oxopent-4-enamides in 28-78% yields, which were cyclized with DMF-DMA in toluene under ambient conditions to afford 4-pyridone-3-carboxamides in 31-70% yields. (C) 2013 Elsevier Ltd. All rights reserved.