(4aS,7R,8aR)-(-)-7-(methoxymethoxy)-1,1,4a-trimethyldecahydronaphthalen-2-one | 153313-20-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aS,7R,8aR)-(-)-7-(methoxymethoxy)-1,1,4a-trimethyldecahydronaphthalen-2-one
• 英文别名: (4aS,7R,8aR)-7-(methoxymethoxy)-1,1,4a-trimethyl-4,5,6,7,8,8a-hexahydro-3H-naphthalen-2-one
• CAS: 153313-20-3
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: QUGAJYLGMUJYSD-XUJVJEKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4aS,7R,8aR)-(-)-7-(methoxymethoxy)-1,1,4a-trimethyldecahydronaphthalen-2-one 在 palladium on activated charcoal 盐酸 、 三氟化硼乙醚 、 甲基锂 、 氢气 、 pyridinium chlorochromate 作用下， 以 甲醇 为溶剂， 生成 (-)-(4aR,8aR)-3,4,4a,5,6,7,8,8a-octahydro-4a,8,8-trimethylnaphthalene-2(1H)-one
  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
• 作为产物：
  描述：

  (4aS,7R,8aR)-(-)-7-(methoxymethoxy)-1,1,4a-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one 在 Rh on carbon 氢气 作用下， 以98%的产率得到(4aS,7R,8aR)-(-)-7-(methoxymethoxy)-1,1,4a-trimethyldecahydronaphthalen-2-one
  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

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.
• Enantiodivergent synthesis of a decalin type of chiral building blocks and their application to terpenoid synthesis
  作者：Naoki Toyooka、Akira Nishino、Takefumi Momose

  DOI：10.1016/s0040-4020(97)00315-3

  日期：1997.5

  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.