ethyl (2S,4aS,7R,8aR)-(-)-2-acetoxy-7-<(1,1-dimethylethyl)dimethylsiloxy>decahydronaphthalene-4a-carboxylate | 190062-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: ethyl (2S,4aS,7R,8aR)-(-)-2-acetoxy-7-<(1,1-dimethylethyl)dimethylsiloxy>decahydronaphthalene-4a-carboxylate
• CAS: 190062-51-2
• 化学式: C₂₁H₃₈O₅Si
• 分子量: 398.615
• InChiKey: RGJMJDAKSNJRMX-IIMDRIAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl (2S,4aS,7R,8aR)-(-)-2-acetoxy-7-<(1,1-dimethylethyl)dimethylsiloxy>decahydronaphthalene-4a-carboxylate 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 ethyl (2S,4aS,7R,8aR)-(-)-2-<(1,1-dimethylethyl)dimethylsiloxy>-7-(methoxymethyl)decahydronaphthalene-4a-carboxylate
  参考文献：
  名称：

  Enantiodivergent synthesis of a decalin type of chiral building blocks and their application to terpenoid synthesis

  摘要：

  An enantiomeric pair of a decalin type of chiral building blocks bearing an oxygenated angular substituent has been synthesized by the lipase-mediated ring differentiation of a meso decahydronaphthalene glycol system Its synthetic utility has been demonstrated by the formal synthesis of (-)-polygodial, (-)-warburganal, (-)-drimenin, and (-)-elemol. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00315-3
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 ethyl (2S,4aR,7R,8aS)-(-)-2-acetoxy-7-hydroxydecahydronaphthalene-4a-carboxylate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 生成 ethyl (2S,4aS,7R,8aR)-(-)-2-acetoxy-7-<(1,1-dimethylethyl)dimethylsiloxy>decahydronaphthalene-4a-carboxylate
  参考文献：
  名称：

  Ring differentiation of the trans-decahydronaphthalene system via chemo-enzymatic dissymmetrization of its σ-symmetric glycol: Synthesis of a highly functionalized chiral building block for the terpene synthesis

  摘要：

  The asymmetric ring differentiation by lipase-catalyzed transesterification of a meso decahydronaphthalenediol (1) was accomplished in extremely high optical and chemical yield. The absolute stereochemistry of the corresponding mono-acetate(-)-2 was determined by its conversion into a decalone [(-)-31 and to an octalone [(+)-4], which were key intermediates for the synthesis of (-)-polygodial, (-)-warburganal, and (-)-drimenin.

  DOI：

  10.1016/0040-4039(93)88079-x