ent-3,12-dioxo-13-epi-manoyl oxide | 159692-16-7

• 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-3,12-dioxo-13-epi-manoyl oxide
• 英文别名: varodione；(3S,4aS,6aS,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-5,6,6a,9,10,10b-hexahydro-1H-benzo[f]chromene-2,8-dione
• CAS: 159692-16-7
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: BGQJYLXYKHRJEI-URYUKNHISA-N

物化性质

• 沸点：
  405.5±45.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ent-3,12-dioxo-13-epi-manoyl oxide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以85%的产率得到ent-3β,12β-dihydroxy-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
• 作为产物：
  描述：

  ent-3β-acetoxy-12α-hydroxy-13-epi-manoyl oxide 在 jones' reagent 、 Curvularia lunata 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 240.0h， 生成 ent-3,12-dioxo-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

文献信息

• Biotransformation of ent -13- epi -manoyl oxides difunctionalized at C-3 and C-12 by filamentous fungi
  作者：Andrés Garcı́a-Granados、Antonia Fernández、Marı́a C. Gutiérrez、Antonio Martı́nez、Raquel Quirós、Francisco Rivas、José M. Arias

  DOI：10.1016/j.phytochem.2003.09.017

  日期：2004.1

  Biotransformation of ent-3beta,12alpha-dihydroxy-13-epi-manoyl oxide with Fusarium moniliforme gave the regioselective oxidation of the hydroxyl group at C-3 and the ent-7beta-hydroxylation. The action of Gliocladium roseum in the 3,12-diketoderivative originated monohydroxylations at C-1 and C-7, both by the ent-beta face, while Rhizopus nigricans produced hydroxylation at C-7 or C-18, epoxidation

  ent-3beta，12alpha-dihydroxy-13-epi-manoyloxide 与 Fusarium moniliforme 的生物转化使区域选择性氧化在 C-3 和 ent-7beta-羟基化的羟基。Gliocladium roseum 在 3,12-二酮衍生物中的作用源自 C-1 和 C-7 的单羟基化，均通过 ent-beta 面，而黑根霉在 C-7 或 C-18 处产生羟基化，双键环氧化，C-3 处酮基的还原，以及 C-2 处生物羟基化/双键环氧化和 C-7 处羟基化/C-3 处酮基还原的组合作用。在 ent-3-hydroxy-12-keto 差向异构体中，G.roseum 起源于 C-1 和 C-7 处的单羟基化，而 R. nigricans 起源于 C-3 处的氧化作为主要转化，双键的环氧化和 C 处的羟基化-2. 最后，