ent-15β-acetoxy-18-chloro-kaur-16-ene | 145224-53-9

• 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-15β-acetoxy-18-chloro-kaur-16-ene
• CAS: 145224-53-9
• 化学式: C₂₂H₃₃ClO₂
• 分子量: 364.956
• InChiKey: GAWMRDROXCRRLF-DUFLWGTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ent-15β-acetoxy-18-chloro-kaur-16-ene 在 氢氧化钾 、 偶氮二异丁腈 、 MAMO 1618 、 三正丁基氢锡 、 碳酸氢钠 作用下， 以 甲醇 、 苯 为溶剂， 反应 4.0h， 生成 ent-11α,13,15β-trihydroxy-kaur-16-ene
  参考文献：
  名称：

  Biotransformation of two ent-15β-hydroxy-kaur-16-ene derivatives by Gibberella fujikuroi

  摘要：

  Incubation of the fungus Gibberella fujikuroi with ent-15beta-hydroxy-kaur-16-ene gave ent-11alpha,15beta-dihydroxy-kaur-16-ene, ent-7beta,11alpha,15beta-trihydroxy-kaur-16-ene,ent-11alpha,13,15beta-trihydroxy-kaur-16-ene,ent-11alpha,15beta,19-trihydroxy-kaur-16-ene, and ent-11alpha,14alpha,15beta-trihydroxy-kaur-16-ene, and a mixture of products, which was resolved by acetylation to give ent-11alpha,14alpha,15beta-triacetoxy-kaur-16-ene and ent-7beta,15beta,17-triacetoxy-11alpha,16alpha-epoxy-kaur-16-ene. The addition of candidiol (ent-15beta,18-dihydroxy-kaur-16-ene)gave ent-11alpha,15beta,18-trihydroxy-kaur-16-ene, and a mixture of substances, which was resolved by acetylation to give ent-11beta,15beta,18-triacetoxy-kaur-16-ene, ent-7beta,11alpha,15beta,18-tetraacetoxy-kaur-16-ene and ent-15beta,17,18-triacetoxy-11alpha,16alpha-epoxykaurane. These results confirm that the presence in ent-kaur-16-ene derivatives of a 15alpha-hydroxyl group inhibits oxidation at C-19 to the acid level. The biotransformation of these compounds may be useful for the synthesis of natural 11beta-hydroxy-ent-kaurene analogues.

  DOI：

  10.1016/s0031-9422(00)97539-3
• 作为产物：
  描述：

  ent-15β-acetoxy-18-hydroxy-kaur-16-ene 在 吡啶 、 四氯化碳 、 三苯基膦 作用下， 反应 4.0h， 生成 ent-15β-acetoxy-18-chloro-kaur-16-ene
  参考文献：
  名称：

  Biotransformation of two ent-15β-hydroxy-kaur-16-ene derivatives by Gibberella fujikuroi

  摘要：

  Incubation of the fungus Gibberella fujikuroi with ent-15beta-hydroxy-kaur-16-ene gave ent-11alpha,15beta-dihydroxy-kaur-16-ene, ent-7beta,11alpha,15beta-trihydroxy-kaur-16-ene,ent-11alpha,13,15beta-trihydroxy-kaur-16-ene,ent-11alpha,15beta,19-trihydroxy-kaur-16-ene, and ent-11alpha,14alpha,15beta-trihydroxy-kaur-16-ene, and a mixture of products, which was resolved by acetylation to give ent-11alpha,14alpha,15beta-triacetoxy-kaur-16-ene and ent-7beta,15beta,17-triacetoxy-11alpha,16alpha-epoxy-kaur-16-ene. The addition of candidiol (ent-15beta,18-dihydroxy-kaur-16-ene)gave ent-11alpha,15beta,18-trihydroxy-kaur-16-ene, and a mixture of substances, which was resolved by acetylation to give ent-11beta,15beta,18-triacetoxy-kaur-16-ene, ent-7beta,11alpha,15beta,18-tetraacetoxy-kaur-16-ene and ent-15beta,17,18-triacetoxy-11alpha,16alpha-epoxykaurane. These results confirm that the presence in ent-kaur-16-ene derivatives of a 15alpha-hydroxyl group inhibits oxidation at C-19 to the acid level. The biotransformation of these compounds may be useful for the synthesis of natural 11beta-hydroxy-ent-kaurene analogues.

  DOI：

  10.1016/s0031-9422(00)97539-3