3-methyl-3-propargylcyclohex-5-en-1,2,4-trione | 1353094-21-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-3-propargylcyclohex-5-en-1,2,4-trione
• 英文别名: 3-Methyl-3-prop-2-ynylcyclohex-5-ene-1,2,4-trione
• CAS: 1353094-21-9
• 化学式: C₁₀H₈O₃
• 分子量: 176.172
• InChiKey: DCXZWLGQYNRFON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  1
• 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-methyl-3-propargylcyclohex-5-en-1,2,4-trione 、 环戊二烯 在 四氯化钛 作用下， 以 甲苯 为溶剂， 以54%的产率得到2,5,5-trimethyltricyclo[4.2.1.0(2,7)]undec-9-en-3,4,6-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
• 作为产物：
  描述：

  2-methyl-2-(1-propyn-3-yl)cyclohexane-1,3-dione 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35%的产率得到3-methyl-3-propargylcyclohex-5-en-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