ethyl 2-fluoro-2-(5-oxo-3-pentyl-5H-chromeno[2,3-b]pyridin-2-yl)acetate | 1257084-70-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: ethyl 2-fluoro-2-(5-oxo-3-pentyl-5H-chromeno[2,3-b]pyridin-2-yl)acetate
• 英文别名: Ethyl 2-fluoro-2-(5-oxo-3-pentylchromeno[2,3-b]pyridin-2-yl)acetate
• CAS: 1257084-70-0
• 化学式: C₂₁H₂₂FNO₄
• 分子量: 371.408
• InChiKey: KYHIJORURISNPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  色酮-3-甲腈 、 (1-ethoxy-2-fluoro-3-trimethylsilyloxynona-1,3-dienoxy)-trimethylsilane 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 以13%的产率得到ethyl 2-fluoro-2-(5-oxo-3-pentyl-5H-chromeno[2,3-b]pyridin-2-yl)acetate
  参考文献：
  名称：

  Synthesis of Highly Functionalized Biaryls by Condensation of 2-Fluoro-1,3-bis(silyloxy) 1,3-Dienes with 3-Cyanochromones and Subsequent Domino “Retro-Michael/Aldol/Fragmentation”

  摘要：

  The Me3SiOTf-mediated condensation of 1-ethoxy-2-fluoro-1,3-bis(trimethylsilyloxy) 1,3-dienes with 3-cyanochromones afforded 3-cyano-2-(4-ethoxy-3-fluoro-2,4-dioxobutyl)-chroman-4-ones. Their reaction with triethylamine afforded fluorinated azaxanthones or biaryls. The product distribution depends on the structure of the diene. The formation of the biaryls can be explained by an unprecedented domino "retro-Michael/aldol/fragmentation" reaction.

  DOI：

  10.1021/jo1018443

文献信息

• Synthesis of Highly Functionalized Biaryls by Condensation of 2-Fluoro-1,3-bis(silyloxy) 1,3-Dienes with 3-Cyanochromones and Subsequent Domino “Retro-Michael/Aldol/Fragmentation”
  作者：Muhammad Farooq Ibad、Obaid-ur-Rahman Abid、Muhammad Adeel、Muhammad Nawaz、Verena Wolf、Alexander Villinger、Peter Langer

  DOI：10.1021/jo1018443

  日期：2010.12.3

  The Me3SiOTf-mediated condensation of 1-ethoxy-2-fluoro-1,3-bis(trimethylsilyloxy) 1,3-dienes with 3-cyanochromones afforded 3-cyano-2-(4-ethoxy-3-fluoro-2,4-dioxobutyl)-chroman-4-ones. Their reaction with triethylamine afforded fluorinated azaxanthones or biaryls. The product distribution depends on the structure of the diene. The formation of the biaryls can be explained by an unprecedented domino "retro-Michael/aldol/fragmentation" reaction.