3-allyl-3-methylcyclohex-5-ene-1,2,4-trione | 1353094-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-allyl-3-methylcyclohex-5-ene-1,2,4-trione
• 英文别名: 3-Methyl-3-prop-2-enylcyclohex-5-ene-1,2,4-trione
• CAS: 1353094-17-3
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: GLDYANDUZDTRQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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-allyl-3-methylcyclohex-5-ene-1,2,4-trione 、 环戊二烯 以 二氯甲烷 为溶剂， 反应 3.0h， 以58%的产率得到5-allyl-3-hydroxy-5-methyltricyclo[4.2.1.0(2,7)]undeca-2,7-diene-4,6-dione
  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
• 作为产物：
  描述：

  2-allyl-2-methyl-1,3-cyclohexanedione 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56%的产率得到3-allyl-3-methylcyclohex-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