ent-17,17'-d2-10β-Hydroxy-20-nor-9α,15α-cyclogibberell-16ene-7,19-dioic acid 7-(methyl ester) 19,10-lactone | 127472-86-0

• 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: ent-17,17'-d2-10β-Hydroxy-20-nor-9α,15α-cyclogibberell-16ene-7,19-dioic acid 7-(methyl ester) 19,10-lactone
• 英文别名: <17,17'-2H2>9,15-cyclo-GA₉-Me；[17,17'-2H2]9,15-cyclo-GA₉-Me
• CAS: 127472-86-0
• 化学式: C₂₀H₂₄O₄
• 分子量: 330.392
• InChiKey: GABCKUAZOCTIQC-SBXGHBIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ent-17,17'-d2-10β-Hydroxy-20-nor-9α,15α-cyclogibberell-16ene-7,19-dioic acid 7-(methyl ester) 19,10-lactone 在 lithium thiopropiolate 作用下， 生成 <17,17'-2H2>9,15-cyclo-GA₉
  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-2β-hydroxy-16-oxo-17,20-dinor-9α,15α-cyclogibberell-1(10)-ene-7,19-dioic acid 7-(methyl ester) 19,2-lactone 在 偶氮二异丁腈 、 bromodiphenylborane 、 三正丁基氢锡 、 四氯化钛 、 potassium carbonate 、 三乙胺 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 23.18h， 生成 ent-17,17'-d2-10β-Hydroxy-20-nor-9α,15α-cyclogibberell-16ene-7,19-dioic acid 7-(methyl ester) 19,10-lactone
  参考文献：
  名称：

  New synthetic pathways from gibberellins to antheridiogens isolated from the fern genus Anemia

  摘要：

  DOI：

  10.1021/jo00303a020