3-cycloheptylcyclopentanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-cycloheptylcyclopentanone
• 英文别名: 3-Cycloheptylcyclopentan-1-one；3-cycloheptylcyclopentan-1-one
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: HLMNSRUUUXFYKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-环戊烯酮 、 环庚烷 在 二苯甲酮 作用下， 以 叔丁醇 为溶剂， 反应 18.0h， 以66%的产率得到3-cycloheptylcyclopentanone
  参考文献：
  名称：

  Photomediated synthesis of β-alkylketones from cycloalkanes

  摘要：

  beta-Cycloalkyl ketones are prepared through a photomediated radical addition reaction onto enones starting from the corresponding alkanes (i.e., cyclopentane, -hexane, -heptane, -dodecane and adamantane). The alkyl radicals are generated via hydrogen abstraction by either an organic (benzophenone) or an inorganic (tetrabutyl ammonium decatungstate, TBADT) photomediator. Isolated yields vary in the range 30-80%. Benzophenone has to be considered as a reagent, since it is used in an equimolar amount with respect to enone and is completely consumed in the reaction. On the contrary, TBADT is shown to behave as a photocatalyst, which is active for at least 50 cycles. The potential of photomediated reactions for the generation of radicals from unusual precursors and the synthetic significance of this method are discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.028

文献信息

• Photomediated synthesis of β-alkylketones from cycloalkanes
  作者：Daniele Dondi、Anna Maria Cardarelli、Maurizio Fagnoni、Angelo Albini

  DOI：10.1016/j.tet.2006.03.028

  日期：2006.6

  beta-Cycloalkyl ketones are prepared through a photomediated radical addition reaction onto enones starting from the corresponding alkanes (i.e., cyclopentane, -hexane, -heptane, -dodecane and adamantane). The alkyl radicals are generated via hydrogen abstraction by either an organic (benzophenone) or an inorganic (tetrabutyl ammonium decatungstate, TBADT) photomediator. Isolated yields vary in the range 30-80%. Benzophenone has to be considered as a reagent, since it is used in an equimolar amount with respect to enone and is completely consumed in the reaction. On the contrary, TBADT is shown to behave as a photocatalyst, which is active for at least 50 cycles. The potential of photomediated reactions for the generation of radicals from unusual precursors and the synthetic significance of this method are discussed. (c) 2006 Elsevier Ltd. All rights reserved.