ent-3β-acetoxy-12β-hydroxy-13-epi-manoyl oxide | 159812-13-2

• 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-3β-acetoxy-12β-hydroxy-13-epi-manoyl oxide
• 英文别名: [(2S,3S,4aS,6aS,8R,10aR,10bS)-3-ethenyl-2-hydroxy-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromen-8-yl] acetate
• CAS: 159812-13-2
• 化学式: C₂₂H₃₆O₄
• 分子量: 364.525
• InChiKey: RQAKPAGNCKWNAV-QKYFFWMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ent-3β-acetoxy-12β-hydroxy-13-epi-manoyl oxide 在 Curvularia lunata 作用下， 以 乙醇 为溶剂， 反应 192.0h， 以9%的产率得到ent-3β,6β,12β-trihydroxy-13-epi-manoyl oxide
  参考文献：
  名称：

  Chemical-microbiological synthesis of ent-13-epi-manoyl oxides with biological activities

  摘要：

  The biotransformation of ent-13-epi-3-keto manoyl oxide, which possesses antileishmania activity, with Curvularia lunata produced ent-6 beta-hydroxy, ent-1 alpha-hydroxy, ent-11 beta-hydroxy and Delta(1)-derivatives, as well as a reduction product at C-3 (S-alcohol) with another hydroxyl group at C-6 (ent-6 beta) or C-11 tent-11 beta). The ent-6 beta-hydroxy and Delta(1)-derivatives inhibited growth of the pathogenic protozoa, Leishmania donovani. The biotransformation of ent-12 alpha-acetoxy-3 beta-hydroxy-13-epi-manoyl oxide and ent-3 beta-acetoxy-12-oxo-13-epi-manoyl oxide gave the ent-6 beta-hydroxyl derivatives. The incubation of ent-3 beta-acetoxy-12 beta-dihydroxy-13-epi-manoyl oxide gave ent-3 beta,12 beta-dihydroxy-13-epi-manoyl oxide and ent-3 beta,6 beta,12 beta-trihydroxy-13-epi-manoyl oxide (trimanoyl). Both products increased the activity of adenylatecyclase.

  DOI：

  10.1016/s0031-9422(00)90350-9
• 作为产物：
  描述：

  ent-3β,12α-dihydroxy-13-epi-manoyl oxide 在 sodium tetrahydroborate 、 jones reagent 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 48.5h， 生成 ent-3β-acetoxy-12β-hydroxy-13-epi-manoyl oxide
  参考文献：
  名称：

  Chemical-microbiological semisynthesis of enantio-Ambrox® derivatives

  摘要：

  enantio-3-Hydroxyambrox derivatives were obtained through combined chemical and microbiological methods from ent-12-oxo-13-epi-manoyl oxides. Regioselective and stereoselective reduction of the carbonyl group at C-3 of ent-3,12-dioxo-13-epi-manoyl oxide was carried out with Baker's yeast. Regioselective acetylation of ent-3,12-dihydroxy-13-epi-manoyl oxide was accomplished with Candida cylindracea lipase or Novozym 435 and vinyl acetate. Microbial biotransformation of enr-3 beta-acetoxy-12-oxo-13-epi-manoyl oxide with Nectria ochroleuca yielded new ent-1 beta-hydroxy- and ent-7 beta-hydroxy derivatives. Baeyer-Villiger oxidation at C-12 was observed in the biotransformation with baker's yeast and G. roseun to obtain norambreinolide lactones which were converted in to enantio-Ambrox((R)) derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00474-3

文献信息

• Chemical-microbiological semisynthesis of enantio-Ambrox® derivatives
  作者：Andrés García-Granados、Antonio Martínez、Raquel Quirós、Antonio Luis Extremera

  DOI：10.1016/s0040-4020(99)00474-3

  日期：1999.7

  enantio-3-Hydroxyambrox derivatives were obtained through combined chemical and microbiological methods from ent-12-oxo-13-epi-manoyl oxides. Regioselective and stereoselective reduction of the carbonyl group at C-3 of ent-3,12-dioxo-13-epi-manoyl oxide was carried out with Baker's yeast. Regioselective acetylation of ent-3,12-dihydroxy-13-epi-manoyl oxide was accomplished with Candida cylindracea lipase or Novozym 435 and vinyl acetate. Microbial biotransformation of enr-3 beta-acetoxy-12-oxo-13-epi-manoyl oxide with Nectria ochroleuca yielded new ent-1 beta-hydroxy- and ent-7 beta-hydroxy derivatives. Baeyer-Villiger oxidation at C-12 was observed in the biotransformation with baker's yeast and G. roseun to obtain norambreinolide lactones which were converted in to enantio-Ambrox((R)) derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Chemical-microbiological synthesis of ent-13-epi-manoyl oxides with biological activities
  作者：Andrés García-Granados、M Belinda Jiménez、Antonio Martínez、Andrés Parra、Francisco Rivas、José María Arias

  DOI：10.1016/s0031-9422(00)90350-9

  日期：1994.11

  The biotransformation of ent-13-epi-3-keto manoyl oxide, which possesses antileishmania activity, with Curvularia lunata produced ent-6 beta-hydroxy, ent-1 alpha-hydroxy, ent-11 beta-hydroxy and Delta(1)-derivatives, as well as a reduction product at C-3 (S-alcohol) with another hydroxyl group at C-6 (ent-6 beta) or C-11 tent-11 beta). The ent-6 beta-hydroxy and Delta(1)-derivatives inhibited growth of the pathogenic protozoa, Leishmania donovani. The biotransformation of ent-12 alpha-acetoxy-3 beta-hydroxy-13-epi-manoyl oxide and ent-3 beta-acetoxy-12-oxo-13-epi-manoyl oxide gave the ent-6 beta-hydroxyl derivatives. The incubation of ent-3 beta-acetoxy-12 beta-dihydroxy-13-epi-manoyl oxide gave ent-3 beta,12 beta-dihydroxy-13-epi-manoyl oxide and ent-3 beta,6 beta,12 beta-trihydroxy-13-epi-manoyl oxide (trimanoyl). Both products increased the activity of adenylatecyclase.