5-hydroxy-8,8-dimethyl-2-propan-2-yl-6,7-dihydro-5H-phenanthrene-3,4-dione

• 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
• 英文名称: 5-hydroxy-8,8-dimethyl-2-propan-2-yl-6,7-dihydro-5H-phenanthrene-3,4-dione
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: PGMGYRXQLKELLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-hydroxy-8,8-dimethyl-2-propan-2-yl-6,7-dihydro-5H-phenanthrene-3,4-dione 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以100%的产率得到1-oxomiltirone
  参考文献：
  名称：

  Semisynthesis of miltirone, 1,2-dehydromiltirone, saligerone from carnosic acid and cytotoxities of their derivatives

  摘要：

  Miltirone, 1,2-dehydromiltirone, saligerone have been synthesized form carnosic acid. Among them, one step transformation of carnosic acid into miltirone was realized when decarboxylation/aromatization was promoted by Lewis acid. Moreover, 4 derivatives exhibited potent cytotoxic activities against three human cancer lines in vitro. (C) 2018 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2018.05.073
• 作为产物：
  描述：

  鼠尾草酸 在 aluminum oxide 、 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 为溶剂， 反应 26.0h， 生成 5-hydroxy-8,8-dimethyl-2-propan-2-yl-6,7-dihydro-5H-phenanthrene-3,4-dione
  参考文献：
  名称：

  Semisynthesis of miltirone, 1,2-dehydromiltirone, saligerone from carnosic acid and cytotoxities of their derivatives

  摘要：

  Miltirone, 1,2-dehydromiltirone, saligerone have been synthesized form carnosic acid. Among them, one step transformation of carnosic acid into miltirone was realized when decarboxylation/aromatization was promoted by Lewis acid. Moreover, 4 derivatives exhibited potent cytotoxic activities against three human cancer lines in vitro. (C) 2018 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2018.05.073