ethyl 2-[(1S,8R,9S,11R)-12-oxatetracyclo[6.3.1.02,7.09,11]dodeca-2,4,6-trien-10-ylidene]acetate | 1476769-33-1

• 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-[(1S,8R,9S,11R)-12-oxatetracyclo[6.3.1.02,7.09,11]dodeca-2,4,6-trien-10-ylidene]acetate
• CAS: 1476769-33-1
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: GBBYUDVQDSANJX-PYHGIMPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(1S,8R,9S,11R)-12-oxatetracyclo[6.3.1.02,7.09,11]dodeca-2,4,6-trien-10-ylidene]acetate 在 copper(ll) bromide 作用下， 以 水 、 乙腈 为溶剂， 反应 10.0h， 以53%的产率得到ethyl 2-[(1S,8R,9S,11R)-9,11-dibromo-12-oxatricyclo[6.3.1.02,7]dodeca-2,4,6-trien-10-ylidene]acetate
  参考文献：
  名称：

  Palladacycle-Catalyzed Methylenecyclopropanation of Bicyclic Alkenes with Propiolates

  摘要：

  An efficient way to access functionalized methylenecyclopropanes has been developed by palladacycle-catalyzed cyclopropanation of bicyclic alkenes with propiolates in high yields. The structure of the palladacycle was kept intact in the reaction, shown by P-31 NMR spectrum studies. A rational mechanism has been proposed with a deuterium-labeled experiment. The usefulness of the functionalized methylenecyclopropanes has also been demonstrated.

  DOI：

  10.1021/jo402024v
• 作为产物：
  描述：

  1,4-epoxy-1,4-dihydronaphthalene 、 丙炔酸乙酯 在 C₆₈H₅₀O₄P₂Pd₂ 、 大茴香酸 作用下， 以 1,2-二氯乙烷 为溶剂， 以84%的产率得到ethyl 2-[(1S,8R,9S,11R)-12-oxatetracyclo[6.3.1.02,7.09,11]dodeca-2,4,6-trien-10-ylidene]acetate
  参考文献：
  名称：

  Palladacycle-Catalyzed Methylenecyclopropanation of Bicyclic Alkenes with Propiolates

  摘要：

  An efficient way to access functionalized methylenecyclopropanes has been developed by palladacycle-catalyzed cyclopropanation of bicyclic alkenes with propiolates in high yields. The structure of the palladacycle was kept intact in the reaction, shown by P-31 NMR spectrum studies. A rational mechanism has been proposed with a deuterium-labeled experiment. The usefulness of the functionalized methylenecyclopropanes has also been demonstrated.

  DOI：

  10.1021/jo402024v