3β-acetoxy-9,15-cyclo-GA9-Me-17-norketone | 138213-39-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3β-acetoxy-9,15-cyclo-GA9-Me-17-norketone
• 英文别名: 3β-acetoxy-9,15-cyclo-GA₉-Me-17-norketone
• CAS: 138213-39-5
• 化学式: C₂₁H₂₄O₇
• 分子量: 388.417
• InChiKey: RUEJQGWTWBOROM-OMFKARKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.42
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  95.97
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-9,15-cyclo-GA9-Me-17-norketone 在 氢氧化钾 、 四氯化钛 、 potassium carbonate 、 锌 作用下， 以 甲醇 为溶剂， 反应 38.58h， 生成 3β-hydroxy-9,15-cyclo-GA₉-Me
  参考文献：
  名称：

  Biosynthesis of antheridic acid, the principal antheridiogen in Anemia phyllitidis

  摘要：

  [(H2)-H-2]9,15-Cyclo-GA9 and [(H2)-H-2]3-alpha-hydroxy-9,15-cyclo-GA9 were fed to prothallia of the fern, Anemia phyllitidis. The metabolites from these feeds were subjected to full-scan GC-MS to confirm the conversion of [(H2)-H-2]9,15-cyclo-GA9 into [(H2)-H-2]3-alpha-hydroxy-9,15-cyclo-GA9 and [(H2)-H-2]antheridic acid, and of [(H2)-H-2]3-alpha-hydroxy-9,15-cyclo-GA9 into [(H2)-H-2]antheridic acid. These results indicated that antheridic acid is biosynthesized from 9,15-cyclo-GA9 via 3-alpha-hydroxy-9,15-cyclo-GA9 in A. phyllitidis. It was also shown that 3-alpha-hydroxy-9,15-cyclo-GA9 is a native antheridiogen in A. phyllitidis. Biological activity of 9,15-cyclo-GA9 and 3-alpha-hydroxy-9,15-cyclo-GA9 are also reported.

  DOI：

  10.1016/0031-9422(91)83186-o
• 作为产物：
  描述：

  ent-3α-Acetoxy-10β-hydroxy-16-oxo-17,20-dinor-9α,15α-cyclogibberell-1(10)-ene-7,19-dioic acid 7-(methyl ester) 19,10-lactone 在 rhodium on alumina 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以36 mg的产率得到3β-acetoxy-9,15-cyclo-GA9-Me-17-norketone
  参考文献：
  名称：

  Biosynthesis of antheridic acid, the principal antheridiogen in Anemia phyllitidis

  摘要：

  [(H2)-H-2]9,15-Cyclo-GA9 and [(H2)-H-2]3-alpha-hydroxy-9,15-cyclo-GA9 were fed to prothallia of the fern, Anemia phyllitidis. The metabolites from these feeds were subjected to full-scan GC-MS to confirm the conversion of [(H2)-H-2]9,15-cyclo-GA9 into [(H2)-H-2]3-alpha-hydroxy-9,15-cyclo-GA9 and [(H2)-H-2]antheridic acid, and of [(H2)-H-2]3-alpha-hydroxy-9,15-cyclo-GA9 into [(H2)-H-2]antheridic acid. These results indicated that antheridic acid is biosynthesized from 9,15-cyclo-GA9 via 3-alpha-hydroxy-9,15-cyclo-GA9 in A. phyllitidis. It was also shown that 3-alpha-hydroxy-9,15-cyclo-GA9 is a native antheridiogen in A. phyllitidis. Biological activity of 9,15-cyclo-GA9 and 3-alpha-hydroxy-9,15-cyclo-GA9 are also reported.

  DOI：

  10.1016/0031-9422(91)83186-o