1-(4-fluorophenyl)-3a,4,7,8-tetrahydro-3a,7,7-trimethylnaphtho[2,3-c]furan-5(3H,6H,9H)-one | 1039747-55-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 1-(4-fluorophenyl)-3a,4,7,8-tetrahydro-3a,7,7-trimethylnaphtho[2,3-c]furan-5(3H,6H,9H)-one
• 英文别名: 3-(4-fluorophenyl)-6,6,9a-trimethyl-4,5,7,9-tetrahydro-1H-benzo[f][2]benzofuran-8-one
• CAS: 1039747-55-1
• 化学式: C₂₁H₂₃FO₂
• 分子量: 326.411
• InChiKey: OONNRHAWTWFWSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-Fluoro-4-[1-(2-methylprop-2-enoxy)prop-2-ynyl]benzene 、 3-碘-5,5-二甲基环己-2-烯-1-酮 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到1-(4-fluorophenyl)-3a,4,7,8-tetrahydro-3a,7,7-trimethylnaphtho[2,3-c]furan-5(3H,6H,9H)-one
  参考文献：
  名称：

  Pd-Catalyzed Sequential Reactions via Allene Intermediate for the Synthesis of Polycyclic Frameworks Containing 2,3-Dihydrofuran Units

  摘要：

  A stepwise process involving Sonogashira coupling, propargyl allenyl isomerization, and consecutive [4 + 2] cyclization has been realized, leading to an efficient synthesis of polycyclic compounds containing a 2,3-dihydrofuran unit. Most attractive for synthetic interest is the finding that up to four stereogenic centers could be generated in one step with high stereoselectivity.

  DOI：

  10.1021/ol801139b

文献信息

• Pd-Catalyzed Sequential Reactions via Allene Intermediate for the Synthesis of Polycyclic Frameworks Containing 2,3-Dihydrofuran Units
  作者：Ruwei Shen、Xian Huang

  DOI：10.1021/ol801139b

  日期：2008.8.7

  A stepwise process involving Sonogashira coupling, propargyl allenyl isomerization, and consecutive [4 + 2] cyclization has been realized, leading to an efficient synthesis of polycyclic compounds containing a 2,3-dihydrofuran unit. Most attractive for synthetic interest is the finding that up to four stereogenic centers could be generated in one step with high stereoselectivity.