3,3-dimethylcyclohex-5-ene-1,2,4-trione | 1353094-16-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3-dimethylcyclohex-5-ene-1,2,4-trione
• 英文别名: 3,3-Dimethylcyclohex-5-ene-1,2,4-trione
• CAS: 1353094-16-2
• 化学式: C₈H₈O₃
• 分子量: 152.15
• InChiKey: XULHHJPUPLNPJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  241.1±33.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3-dimethylcyclohex-5-ene-1,2,4-trione 、 环戊二烯 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 5,5-Dimethyltricyclo[6.2.1.02,7]undec-9-ene-3,4,6-trione
  参考文献：
  名称：

  路易斯酸对 3,3,6-Trimethylcyclohex-5-ene-1,2,4-trione 环加成反应的影响：氢转移与环戊二烯环加成反应

  摘要：

  将 3,3,6-trimethylcyclohex-5-ene-1,2,4-trione 暴露于催化量的路易斯酸中，在环戊二烯存在下发生了两种不同的反应。发现预期的环加成对于标题化合物是可逆的，并且转移氢化是长时间的优选途径。其他测试的底物能够以相当大的产率进行轻松的环加成反应，并且没有平行还原。

  DOI：

  10.1002/ejoc.201300706
• 作为产物：
  描述：

  2,2-二甲基-1,3-环己烷二酮 在 N-(2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-yl)acetamide tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以65%的产率得到3,3-dimethylcyclohex-5-ene-1,2,4-trione
  参考文献：
  名称：

  Access to Dienophilic Ene-Triketone Synthons by Oxidation of Diketones with an Oxoammonium Salt

  摘要：

  Here we describe the oxidation of 1,3-cyclohexanediones with 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (Bobbitt's salt) to generate 5-ene-1,2,4-triones in moderate-to-good (40-80%) yields. This inexpensive oxidant facilitated an unprecedented cascade of oxidation and elimination to yield novel ene-triketones. The reactivity of these products was explored in the Diets-Alder reaction and provided moderate-to-good yields of cycloaddition products. The products described in this study represent unique, densely functionalized, and versatile building blocks for the synthesis of more complex molecules.

  DOI：

  10.1021/ol2030873

文献信息

• The Effect of Lewis Acids on the Cycloaddition of 3,3,6-Trimethylcyclohex-5-ene-1,2,4-trione: Hydrogen Transfer versus Cycloaddition with Cyclopentadiene
  作者：Nicholas A. Eddy、Jay J. Richardson、Gabriel Fenteany

  DOI：10.1002/ejoc.201300706

  日期：2013.8

  Exposure of 3,3,6-trimethylcyclohex-5-ene-1,2,4-trione to catalytic amounts of Lewis acids revealed two disparate reactions in the presence of cyclopentadiene. The expected cycloaddition was found to be reversible for the title compound, and transfer hydrogenation was the preferred pathway over long periods of time. Other tested substrates were able to undergo facile cycloaddition with considerable

  将 3,3,6-trimethylcyclohex-5-ene-1,2,4-trione 暴露于催化量的路易斯酸中，在环戊二烯存在下发生了两种不同的反应。发现预期的环加成对于标题化合物是可逆的，并且转移氢化是长时间的优选途径。其他测试的底物能够以相当大的产率进行轻松的环加成反应，并且没有平行还原。
• Access to Dienophilic Ene-Triketone Synthons by Oxidation of Diketones with an Oxoammonium Salt
  作者：Nicholas A. Eddy、Christopher B. Kelly、Michael A. Mercadante、Nicholas E. Leadbeater、Gabriel Fenteany

  DOI：10.1021/ol2030873

  日期：2012.1.20

  Here we describe the oxidation of 1,3-cyclohexanediones with 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (Bobbitt's salt) to generate 5-ene-1,2,4-triones in moderate-to-good (40-80%) yields. This inexpensive oxidant facilitated an unprecedented cascade of oxidation and elimination to yield novel ene-triketones. The reactivity of these products was explored in the Diets-Alder reaction and provided moderate-to-good yields of cycloaddition products. The products described in this study represent unique, densely functionalized, and versatile building blocks for the synthesis of more complex molecules.