fujenoic acid | 6750-12-5

• 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: fujenoic acid
• 英文别名: (1R,2S,5R)-2-[(3aS,4S,7aR)-4,7a-dimethyl-1,3-dioxo-3a,5,6,7-tetrahydro-2-benzofuran-4-yl]-6-methylidenebicyclo[3.2.1]octane-1-carboxylic acid
• CAS: 6750-12-5
• 化学式: C₂₀H₂₆O₅
• 分子量: 346.423
• InChiKey: VANVHXWMIRKGSW-CQVYYPFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  fujenoic acid 、 重氮甲烷 在 甲醇 作用下， 以 乙醚 为溶剂， 反应 40.0h， 以5 mg的产率得到(1R,2S,3S)-3-((1R,2S,5R)-1-Methoxycarbonyl-6-methylene-bicyclo[3.2.1]oct-2-yl)-1,3-dimethyl-cyclohexane-1,2-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Biotransformation of 7-oxo-ent-kaur-16-ene derivatives by Gibberella fujikuroi

  摘要：

  The microbiological transformation of 7-oxo-ent-kaur-16-ene by the fungus Gibberella fujikuroi gave fujenoic acid as the main compound, whilst the incubation of 18-hydroxy-7-oxo-ent-kaur-16-ene and 3 alpha,18-dihydroxy-7-oxo-ent-kaur-16-ene afforded the corresponding 6 beta-hydroxy-derivatives. These facts indicate that the formation of fujenoic acid in this biotransformation should occur via a 7-oxo-6 beta-hydroxy derivative. In the three biotransformations. an 11 beta-hydroxylation was also produced. in low yield, indicating that a 7-oxo-group also directs hydroxylation at C-11. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.089
• 作为产物：
  描述：

  7-oxo-ent-kaur-16-ene 在 AMO 1618 、 Gibberella fujikuroi IMI 58289 作用下， 以 乙醇 为溶剂， 反应 144.0h， 以11 mg的产率得到fujenoic acid
  参考文献：
  名称：

  Biotransformation of 7-oxo-ent-kaur-16-ene derivatives by Gibberella fujikuroi

  摘要：

  The microbiological transformation of 7-oxo-ent-kaur-16-ene by the fungus Gibberella fujikuroi gave fujenoic acid as the main compound, whilst the incubation of 18-hydroxy-7-oxo-ent-kaur-16-ene and 3 alpha,18-dihydroxy-7-oxo-ent-kaur-16-ene afforded the corresponding 6 beta-hydroxy-derivatives. These facts indicate that the formation of fujenoic acid in this biotransformation should occur via a 7-oxo-6 beta-hydroxy derivative. In the three biotransformations. an 11 beta-hydroxylation was also produced. in low yield, indicating that a 7-oxo-group also directs hydroxylation at C-11. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.089