ent-3-oxosclareolide | 245054-21-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: ent-3-oxosclareolide
• 英文别名: (3aS,5aS,9aR,9bS)-3a,6,6,9a-tetramethyl-4,5,5a,8,9,9b-hexahydro-1H-benzo[e][1]benzofuran-2,7-dione
• CAS: 245054-21-1
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: JQBCYOREBVVBBP-CJTUPEFNSA-N

物化性质

• 沸点：
  389.3±42.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 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-oxosclareolide 在 lithium aluminium tetrahydride 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 73.0h， 生成 ent-3β-hydroxyambrox
  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,12α-dihydroxy-13-epi-manoyl oxide 在 jones reagent 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 288.0h， 生成 ent-3-oxosclareolide
  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.