<5-13C>-5-Cyclodecynone | 154276-52-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <5-13C>-5-Cyclodecynone
• 英文别名: 5-<13C>-bicyclo<4.4.0>-1(6)-decen-2-one；(513C)cyclodec-5-yn-1-one
• CAS: 154276-52-5
• 化学式: C₁₀H₁₄O
• 分子量: 151.21
• InChiKey: UXJBMXUARWYMJT-LBPDFUHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  <5-13C>-5-Cyclodecynone 以69%的产率得到
  参考文献：
  名称：

  Wempe Michael F., Grunwell John R., J. Org. Chem, 60 (1995) N 9, S 2714-2720

  摘要：

  DOI：
• 作为产物：
  描述：

  11-oxatricyclo[4.4.1.01,5]undecan-10-one 以58%的产率得到
  参考文献：
  名称：

  Wempe Michael F., Grunwell John R., J. Org. Chem, 60 (1995) N 9, S 2714-2720

  摘要：

  DOI：

文献信息

• The transannular rearrangement of 5-cyclodecynone
  作者：John R. Grunwell、Michael F. Wempe、Judith Mitchell、Jocelyn R. Grunwell

  DOI：10.1016/s0040-4039(00)79277-x

  日期：1993.11

  The acid catalyzed rearrangement of 5-cyclodecynone to bicyclo[4.4.0]-1(6)-decen-2-one has been shown by carbon thirteen labeling experiments to proceed by a mechanism that does not involve an enol of 5-cyclodecynone

  十三碳标记实验表明，酸催化的5-环癸酮重排为双环[4.4.0] -1（6）-癸烯-2-酮的反应机理与5-环癸酮的烯醇无关
• The Transannular Rearrangement of 5-Cyclodecynone
  作者：Michael F. Wempe、John R. Grunwell

  DOI：10.1021/jo00114a018

  日期：1995.5

  The acid-catalyzed rearrangement of 5-cyclodecynone (1) to bicyclo[4.4.0]-1(6)-decen-2-one (5) has been investigated via C-13 and deuterium labeling experiments, which showed that the transannular rearrangement proceeds by a mechanism not involving an enol of 5-cyclodecynone. Subjecting 5-cyclodecynone to NBS in ethyl ether resulted in the formation of a dibromooxetane 21 which arose from a bromo allylic alcohol 20 formed from 5-cyclodecynone and HBr. The chloro allylic alcohol 28 was formed from HCl and was subsequently converted to enone 5. Pathways were investigated using AM1 calculations. As a result, a modified mechanism consistent with all the experimental data is proposed for the acid-catalyzed rearrangement of 1 to 5.