ent-7α-acetoxy-16β,17-epoxykaurane | 159691-95-9

• 英文名称: ent-7α-acetoxy-16β,17-epoxykaurane
• 英文别名: [(1'R,2R,2'S,4'R,9'R,10'S,13'R)-5',5',9'-trimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.01,10.04,9]hexadecane]-2'-yl] acetate
• CAS: 159691-95-9
• 化学式: C₂₂H₃₄O₃
• 分子量: 346.51
• InChiKey: TYQNKSZWZVKFCX-BJWFUVPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ent-7α-acetoxy-16β,17-epoxykaurane 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以10 mg的产率得到ent-16β,17-epoxy-7α-hydroxykaurane
  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：

  candol A acetate 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 7.0h， 以12 mg的产率得到ent-7α-acetoxy-16β,17-epoxykaurane
  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