4-oxacycloundecyne-3,6-dione | 1613315-80-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-oxacycloundecyne-3,6-dione
• 英文别名: 1-Oxacycloundec-3-yne-2,10-dione；1-oxacycloundec-3-yne-2,10-dione
• CAS: 1613315-80-2
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: SDUXBXOKRWWWBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氧代-1-环庚烷甲酸甲酯 在 吡啶 、 2,5-二甲基吡啶 、 N,N′-双(对甲苯磺酰)肼 、 palladium 10% on activated carbon 、 氧气 、 四氯化锡 、 二异丁基氢化铝 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 cesium fluoride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 14.17h， 生成 4-oxacycloundecyne-3,6-dione
  参考文献：
  名称：

  Fragmentation of Bicyclic γ-Silyloxy-β-hydroxy-α-diazolactones as an Approach to Ynolides

  摘要：

  Medium-sized ynolides were prepared by the Lewis acid-mediated fragmentation of bicyclic gamma-silyloxy-beta-hydroxy-alpha-diazolactones in which the C beta-C gamma bond is the ring fusion bond. Although these lactone fragmentation substrates reacted somewhat less efficiently than their carbocyclic counterparts, the fragmentation provided 11-membered ynolides in up to 84% yield. Unlike prior fragmentations of similar substrates, elevated temperatures were required to obtain optimum yields of the ynolide products. The ynolides reported herein have ring sizes of 10 or 11, which are the smallest reported to date.

  DOI：

  10.1021/jo500634d

文献信息

• Fragmentation of Bicyclic γ-Silyloxy-β-hydroxy-α-diazolactones as an Approach to Ynolides
  作者：Ali Bayir、Matthias Brewer

  DOI：10.1021/jo500634d

  日期：2014.7.3

  Medium-sized ynolides were prepared by the Lewis acid-mediated fragmentation of bicyclic gamma-silyloxy-beta-hydroxy-alpha-diazolactones in which the C beta-C gamma bond is the ring fusion bond. Although these lactone fragmentation substrates reacted somewhat less efficiently than their carbocyclic counterparts, the fragmentation provided 11-membered ynolides in up to 84% yield. Unlike prior fragmentations of similar substrates, elevated temperatures were required to obtain optimum yields of the ynolide products. The ynolides reported herein have ring sizes of 10 or 11, which are the smallest reported to date.