2-异丙基-8-甲基-5,6,7,8-四氢-3,4-菲二酮 | 127791-76-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 2-异丙基-8-甲基-5,6,7,8-四氢-3,4-菲二酮
• 中文别名: 4-[2-[二[2-(1-乙基吡啶-4-基)乙基]磷基]乙基]-1-乙基-吡啶并英三碘化
• 英文名称: 2-Isopropyl-5,6,7,8-tetrahydro-8-methyl-3,4-phenanthrenedione
• 英文别名: 8-methyl-2-propan-2-yl-5,6,7,8-tetrahydrophenanthrene-3,4-dione
• CAS: 127791-76-8
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: RVDHNMHKKQZVSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-异丙基邻苯二酚 、 6-methyl-1-vinyl-cyclohexene 在 silver(l) oxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以80%的产率得到2-异丙基-8-甲基-5,6,7,8-四氢-3,4-菲二酮
  参考文献：
  名称：

  Synthesis and Antioxidant Activity of Rosmariquinone and Several Analogues

  摘要：

  Rosmariquinone (1) and six analogues were chemically synthesized using an ultrasound-promoted Diels-Alder cycloaddition in yields of 35-90%. The analogues included substitution of the isopropyl at carbon 13 (C-13) with a hydrogen (5), methyl (6), or tert-butyl (4) substituent. The hydrogen-substituted analogue had the lowest yield at 35%, due in part to the instability of the compound to air, while the highest yields were achieved for the methyl (85%) and tert-butyl (90%) analogues. The 60% yield obtained for the C-14 methyl analogue (7; no C-13 isopropyl) may have been caused by the meta-substituted catechol inhibiting the cycloaddition. The final two analogues were ring A modifications and included the removal of one C-4 methyl (3; 80% yield) or both C-4 methyl (2; 85% yield) groups. The analogues were tested against rosmariquinone in light-sensitized oxidation of stripped soybean oil. Analogues 5 and 6 were significantly (P < 0.05) better antioxidants than rosmariquinone and all other analogues. The antioxidant properties of compounds 2-7 were not significantly different (P < 0.05) from each other while compounds 2 and 4 had significantly (P < 0.05) lower antioxidant activity than rosmariquinone. This study demonstrated the importance of structural characteristics of antioxidants and that natural antioxidants, such as rosmariquinone, can be improved through chemical modification.

  DOI：

  10.1021/jf970742k

文献信息

• Synthesis of miltirone by an ultrasound-promoted cycloaddition
  作者：Junning Lee、Hsiao Shan Mei、John K. Snyder

  DOI：10.1021/jo00304a010

  日期：1990.8
• LEE, JUNNING;SHAN, MEI HSIAO;SNYDER, JOHN K., J. ORG. CHEM., 55,(1990) N7, C. 5013-5016
  作者：LEE, JUNNING、SHAN, MEI HSIAO、SNYDER, JOHN K.

  DOI：——

  日期：——
• Synthesis and Antioxidant Activity of Rosmariquinone and Several Analogues
  作者：Clifford A. Hall、Susan L. Cuppett、Pat Dussault

  DOI：10.1021/jf970742k

  日期：1998.4.1

  Rosmariquinone (1) and six analogues were chemically synthesized using an ultrasound-promoted Diels-Alder cycloaddition in yields of 35-90%. The analogues included substitution of the isopropyl at carbon 13 (C-13) with a hydrogen (5), methyl (6), or tert-butyl (4) substituent. The hydrogen-substituted analogue had the lowest yield at 35%, due in part to the instability of the compound to air, while the highest yields were achieved for the methyl (85%) and tert-butyl (90%) analogues. The 60% yield obtained for the C-14 methyl analogue (7; no C-13 isopropyl) may have been caused by the meta-substituted catechol inhibiting the cycloaddition. The final two analogues were ring A modifications and included the removal of one C-4 methyl (3; 80% yield) or both C-4 methyl (2; 85% yield) groups. The analogues were tested against rosmariquinone in light-sensitized oxidation of stripped soybean oil. Analogues 5 and 6 were significantly (P < 0.05) better antioxidants than rosmariquinone and all other analogues. The antioxidant properties of compounds 2-7 were not significantly different (P < 0.05) from each other while compounds 2 and 4 had significantly (P < 0.05) lower antioxidant activity than rosmariquinone. This study demonstrated the importance of structural characteristics of antioxidants and that natural antioxidants, such as rosmariquinone, can be improved through chemical modification.