3-Acetyl-2-hydroxy-9-methoxy-5-(trifluoromethyl)-5H-chromeno[3,4-b]pyridine | 1437305-29-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-Acetyl-2-hydroxy-9-methoxy-5-(trifluoromethyl)-5H-chromeno[3,4-b]pyridine
• 英文别名: 1-[2-hydroxy-9-methoxy-5-(trifluoromethyl)-5H-chromeno[3,4-b]pyridin-3-yl]ethanone
• CAS: 1437305-29-7
• 化学式: C₁₆H₁₂F₃NO₄
• 分子量: 339.271
• InChiKey: FWNUKFWGBLCHDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  68.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (E)-5-[(2R,3S,4R)-6-methoxy-3-nitro-2-(trifluoromethyl)-3,4-dihydro-2H-chromen-4-yl]-4-morpholin-4-ylpent-3-en-2-one 在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以34%的产率得到3-Acetyl-2-hydroxy-9-methoxy-5-(trifluoromethyl)-5H-chromeno[3,4-b]pyridine
  参考文献：
  名称：

  Synthesis of 5-(trifluoromethyl)-5H-chromeno[3,4-b]pyridines from 3-nitro-2-(trifluoromethyl)-2H-chromenes and aminoenones derived from acetylacetone and cyclic amines

  摘要：

  Reactions of 3-nitro-2H-chromenes with aminoenones derived from acetylacetone and cyclic amines proceed diastereoselectively to give functionalized 2,3,4-trisubstituted chromanes as a result of nucleophilic addition of the vinylogous beta-methyl group at the C-4 atom of the chromene system. From these compounds, under acidic conditions, 5-(trifluoromethyl)-5H-chromeno[3,4-b]pyridines and 4-acetoacetonyl-3-nitro-2-(trichloromethyl/phenyl)chromanes, depending on the substituent at the 2-position, were obtained in moderate to good yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.137