methyl 13-hydroxy-7-oxo-8,11,13-podocarpatrien-19-oate | 864060-45-7

• 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: methyl 13-hydroxy-7-oxo-8,11,13-podocarpatrien-19-oate
• 英文别名: methyl (1S,4aS,10aR)-7-hydroxy-1,4a-dimethyl-9-oxo-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylate
• CAS: 864060-45-7
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: RZAQYGXKTKKXNJ-NXHRZFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 8,13-dioxo-14,15,17-trinorlabdan-19-oate 在 air 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以80%的产率得到methyl 13-hydroxy-7-oxo-8,11,13-podocarpatrien-19-oate
  参考文献：
  名称：

  A New Route toward 7-Oxo-13-hydroxy-8,11,13-podocarpatrienes from Labdane Diterpenes

  摘要：

  Trinorlabdane 1,5-diketones (7, 10a, b, 13a,b), which are easily prepared from labdane diterpenes, are directly converted into the corresponding 7-oxo-13-hydroxy-8,11,13-podocarpatrienes, immediate precursors of bioactive compounds, under basic treatment. Utilizing this strategy, the first enantiospecific synthesis of 13-hydroxy-8,11,13-podocarpatriene (20), a constituent of Taiwania cryptomerioides, was achieved starting from (-)- sclareol ( 5) after a seven-step sequence in 55% overall yield.

  DOI：

  10.1021/np0502847

文献信息

• A New Route toward 7-Oxo-13-hydroxy-8,11,13-podocarpatrienes from Labdane Diterpenes
  作者：Enrique Alvarez-Manzaneda Roldán、Juan Luis Romera Santiago、Rachid Chahboun

  DOI：10.1021/np0502847

  日期：2006.4.1

  Trinorlabdane 1,5-diketones (7, 10a, b, 13a,b), which are easily prepared from labdane diterpenes, are directly converted into the corresponding 7-oxo-13-hydroxy-8,11,13-podocarpatrienes, immediate precursors of bioactive compounds, under basic treatment. Utilizing this strategy, the first enantiospecific synthesis of 13-hydroxy-8,11,13-podocarpatriene (20), a constituent of Taiwania cryptomerioides, was achieved starting from (-)- sclareol ( 5) after a seven-step sequence in 55% overall yield.