3-(3-(allyloxy)-3-phenylprop-1-yn-1-yl)cyclohex-2-en-1-one | 1039747-35-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3-(allyloxy)-3-phenylprop-1-yn-1-yl)cyclohex-2-en-1-one
• CAS: 1039747-35-7
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: IHTHQRWSPVRCGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(3-(allyloxy)-3-phenylprop-1-yn-1-yl)cyclohex-2-en-1-one 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以82%的产率得到3a,4,7,8-tetrahydro-1-phenylnaphtho[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
• 作为产物：
  描述：

  3-Iodocyclohex-2-enone 、 (1-(allyloxy)prop-2-ynyl)benzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以19%的产率得到3a,4,7,8-tetrahydro-1-phenylnaphtho[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