ent-3α,8α,12-trihydroxy-13,14,15,16-tetranorlabdane | 245054-22-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ent-3α,8α,12-trihydroxy-13,14,15,16-tetranorlabdane
• 英文别名: (1S,2S,4aS,6S,8aR)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,6-diol
• CAS: 245054-22-2
• 化学式: C₁₆H₃₀O₃
• 分子量: 270.412
• InChiKey: LNIIQGGPYSTYTR-GADBESIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ent-3α,8α,12-trihydroxy-13,14,15,16-tetranorlabdane 在 对甲苯磺酰氯 作用下， 以 吡啶 为溶剂， 反应 12.0h， 以50%的产率得到ent-3α-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 lithium aluminium tetrahydride 、 jones reagent 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 144.5h， 生成 ent-3α,8α,12-trihydroxy-13,14,15,16-tetranorlabdane
  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