(2S,4aR,7R,8aR)-(+)-2-hydroxy-7-(methoxymethoxy)-4a-methyldecahydronaphthalene | 152089-97-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4aR,7R,8aR)-(+)-2-hydroxy-7-(methoxymethoxy)-4a-methyldecahydronaphthalene
• CAS: 152089-97-9
• 化学式: C₁₃H₂₄O₃
• 分子量: 228.332
• InChiKey: LONFYDCTWVMIKI-YVECIDJPSA-N

物化性质

• 沸点：
  306.2±22.0 °C(predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,4aR,7R,8aR)-(+)-2-hydroxy-7-(methoxymethoxy)-4a-methyldecahydronaphthalene 在 六甲基磷酰三胺 、 palladium diacetate 、 三甲基氯硅烷 、 pyridinium chlorochromate 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 22.83h， 生成 (1S,4aS,7R,8aS)-7-(methoxymethoxy)-1,4a-dimethyl-1,5,6,7,8,8a-hexahydronaphthalen-2-one
  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：

  ethyl (2S,4aR,7R,8aS)-(-)-2-acetoxy-7-hydroxydecahydronaphthalene-4a-carboxylate 在 咪唑 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 四丁基氟化铵 、 碘 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 63.5h， 生成 (2S,4aR,7R,8aR)-(+)-2-hydroxy-7-(methoxymethoxy)-4a-methyldecahydronaphthalene
  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

文献信息

• 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
  作者：Naoki Toyooka、Akira Nishino、Takefumi Momose

  DOI：10.1016/0040-4039(93)88079-x

  日期：1993.7

  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.