<1-13C>-α-Tetralone | 85687-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: <1-13C>-α-Tetralone
• 英文别名: 3,4-dihydro-2H-naphthalen-1-one
• CAS: 85687-70-3
• 化学式: C₁₀H₁₀O
• 分子量: 147.178
• InChiKey: XHLHPRDBBAGVEG-DETAZLGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  <1-13C>-α-Tetralone 在 Rh/Al₂O₃ 氢气 作用下， 生成 <1-13C>-α-Decalol
  参考文献：
  名称：

  5-环癸酮的跨环重排

  摘要：

  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

  DOI：

  10.1016/s0040-4039(00)79277-x
• 作为产物：
  描述：

  <1-13C>-4-Phenylbutyric acid 在 PPA 作用下， 生成 <1-13C>-α-Tetralone
  参考文献：
  名称：

  5-环癸酮的跨环重排

  摘要：

  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

  DOI：

  10.1016/s0040-4039(00)79277-x

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
• 13C13C spin coupling constants in tetrahydronaphthylene, hexahydrobenzanthracene and benzo[a]pyrene derivatives
  作者：Richard H. Cox、Louis A. Levy

  DOI：10.1002/omr.1270210305

  日期：1983.3

  AbstractThe 13C13C spin coupling constants have been determined in substituted [1‐13C]tetrahydronaphthylenes, [5‐13C]hexahydrobenzanthracenes and [5‐13C]benzanthracene. In addition, the 13C13C spin coupling constants for 7‐hydroxy[7‐13C]benzopyrene, trans‐7,8‐dihydro[7‐13C]benzopyrene‐7,8‐diol and trans‐7,8‐dihydro[10‐13C]benzopyrene‐7,8‐diol are reported, together with the one‐bond carbon‐carbon coupling constants between C‐4 and C‐5 in selected 4,5‐disubstituted benzopyrenes. Values for the directly bonded coupling constants and long‐range coupling constants are similar to those reported previously for other aromatic and aliphatic systems. Substituent effects on carbon‐carbon coupling are compared for similarly substituted cyclic and acyclic systems.
• Wempe Michael F., Grunwell John R., J. Org. Chem, 60 (1995) N 9, S 2714-2720
  作者：Wempe Michael F., Grunwell John R.

  DOI：——

  日期：——
• PICKERING, R. E.;BYMASTER, D. L.;EISENBRAUN, E. J., J. LABELLED COMPOUNDS AND RADIOPHARM., 1985, 22, N 11, 1149-1154
  作者：PICKERING, R. E.、BYMASTER, D. L.、EISENBRAUN, E. J.

  DOI：——

  日期：——
• 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.