3-Oxabicyclo[8.4.0]tetradeca-1(14),10,12-trien-8-yn-2-one | 1620513-30-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Oxabicyclo[8.4.0]tetradeca-1(14),10,12-trien-8-yn-2-one
• CAS: 1620513-30-5
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: YXGCFYZSQDZHMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Boc-3-氮杂环丁酮 、 3-Oxabicyclo[8.4.0]tetradeca-1(14),10,12-trien-8-yn-2-one 在 bis(triphenylphosphine)nickel(II) chloride 、 锌 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以55%的产率得到tert-butyl 4,10-dioxo-4,5,6,7,8,10-hexahydro-1H-benzo[3,4]-oxecino[5,6-c]pyridine-2(3H)-carboxylate
  参考文献：
  名称：

  An in Situ Approach to Nickel-Catalyzed Cycloaddition of Alkynes and 3-Azetidinones

  摘要：

  An efficient and convenient procedure that generates the active Ni(0) catalyst in situ from cheap, air stable Ni(II) precursors is developed for the [4 + 2]-cycloaddition of alkynes and 3-azetidinones. The reaction affords useful 3-dehydropiperidinones in comparable yields to the reported Ni(0) procedure. Additionally, the cycloaddition with 3-oxetanone afforded the 3-dehydropyranone product. Chiral 2-substituted azetidinones were also tolerated to form substituted dehydropiperidinones in high yield and enantiomeric excess.

  DOI：

  10.1021/acs.joc.5b01458
• 作为产物：
  描述：

  hex-5-yn-1-yl 2-iodobenzoate 在 1,10-菲罗啉 、 caesium carbonate 、 copper(l) chloride 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以46%的产率得到3-Oxabicyclo[8.4.0]tetradeca-1(14),10,12-trien-8-yn-2-one
  参考文献：
  名称：

  Cu(I)-Catalyzed Macrocyclic Sonogashira-Type Cross-Coupling

  摘要：

  A macrocyclic Cu-catalyzed Sonogashira-type cross-coupling reaction has been developed that employs an operationally simple CuCl/phen/Cs2CO3 catalyst system. Macrocyclizations can be performed at relatively high concentrations without the need for slow addition techniques and form macrocycles with various ring sizes and functional groups. The optimized protocol was employed in the synthesis of (S)-zearalane, demonstrating applicability toward the synthesis of a macrocycle with known biological activity.

  DOI：

  10.1021/ol501898b