ethyl 2-fluoro-3-oxononanoate | 1257085-30-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl 2-fluoro-3-oxononanoate
• CAS: 1257085-30-5
• 化学式: C₁₁H₁₉FO₃
• 分子量: 218.268
• InChiKey: OGRMXMUHIUJERK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 ethyl 2-fluoro-3-oxononanoate 在 三乙胺 作用下， 以 苯 为溶剂， 反应 48.0h， 以65%的产率得到ethyl 2-fluoro-3-trimethylsilyloxynon-2-enoate
  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
• 作为产物：
  描述：

  1-碘戊烷 、 2-氟乙酰乙酸乙酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以74%的产率得到ethyl 2-fluoro-3-oxononanoate
  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.