ent-7α,16β,17-trihydroxykaurane | 145700-97-6

• 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-7α,16β,17-trihydroxykaurane
• 英文别名: (1R,2S,4R,9R,10S,13R,14R)-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-2,14-diol
• CAS: 145700-97-6
• 化学式: C₂₀H₃₄O₃
• 分子量: 322.488
• InChiKey: PVLZQLBPEVSLOY-XKBPDVHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 ent-7α,16β,17-trihydroxykaurane 以 吡啶 为溶剂， 反应 2.0h， 生成 [(1R,2S,4R,9R,10S,13R,14R)-2-acetyloxy-14-hydroxy-5,5,9-trimethyl-14-tetracyclo[11.2.1.01,10.04,9]hexadecanyl]methyl acetate
  参考文献：
  名称：

  The microbiological transformation of two ent-16β,17-epoxykaurane derivatives by Gibberella fujikuroi

  摘要：

  The biotransformation of ent-16 beta,17-epoxy-7 alpha-hydroxykaurane by Gibberella fujikuroi affords ent-7 alpha,11 alpha,16 beta,17-tetrahydroxykaurane and ent-7 alpha,9 alpha,16 beta,17-tetrahydroxykaurane. These results indicated that the presence of the 16 alpha,17-diol group, into which the 16 alpha,17-epoxy is transformed in the medium, inhibits oxidation at C-19 and favours hydroxylation at C-11(beta). Incubation of ent-16 beta,17-epoxykauran-19-oic acid, via the 16 alpha,17-diol, gave the 7-aldehyde of 16 alpha,17-dihydroxy-GA(12).

  DOI：

  10.1016/s0031-9422(00)90345-5
• 作为产物：
  描述：

  ent-16,17-epoxy-7α-hydroxykaurane 在 Gibberella fujikuroi 作用下， 以 乙醇 为溶剂， 反应 144.0h， 以8 mg的产率得到ent-7α,9α,16β,17-tetrahydroxykaurane
  参考文献：
  名称：

  The microbiological transformation of two ent-16β,17-epoxykaurane derivatives by Gibberella fujikuroi

  摘要：

  The biotransformation of ent-16 beta,17-epoxy-7 alpha-hydroxykaurane by Gibberella fujikuroi affords ent-7 alpha,11 alpha,16 beta,17-tetrahydroxykaurane and ent-7 alpha,9 alpha,16 beta,17-tetrahydroxykaurane. These results indicated that the presence of the 16 alpha,17-diol group, into which the 16 alpha,17-epoxy is transformed in the medium, inhibits oxidation at C-19 and favours hydroxylation at C-11(beta). Incubation of ent-16 beta,17-epoxykauran-19-oic acid, via the 16 alpha,17-diol, gave the 7-aldehyde of 16 alpha,17-dihydroxy-GA(12).

  DOI：

  10.1016/s0031-9422(00)90345-5