(1R,4S,4aR,8aS)-4-[(methylsulfonyl)oxy]-decahydronaphthalen-1-yl acetate | 821788-46-9

• 英文名称: (1R,4S,4aR,8aS)-4-[(methylsulfonyl)oxy]-decahydronaphthalen-1-yl acetate
• CAS: 821788-46-9
• 化学式: C₁₃H₂₂O₅S
• 分子量: 290.381
• InChiKey: MDCKLRRKTNUPMP-LOWDOPEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,4S,4aR,8aS)-4-[(methylsulfonyl)oxy]-decahydronaphthalen-1-yl acetate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 20.0 ℃ 、379.21 kPa 条件下， 反应 6.0h， 生成 (1R,4aS,8aS)-decahydronaphthalen-1-ol
  参考文献：
  名称：

  Enzymatic desymmetrization of meso-1α,4α-dihydroxy-cis-decalins

  摘要：

  The stereoselective acetylation of meso-decalindiols I and 2 by vinyl acetate in the presence of Candida antarctica lipase gave monoester (1R,4S,4aR,8aS)-5 and (1R,4S,4aR,8aS)-6 in high enantiomeric excess (ee greater than or equal to 98%). The hydrolysis of the corresponding meso-diacetates 3 and 4 in the presence of porcine liver esterase in phosphate buffer provided the opposite enantiomers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.004
• 作为产物：
  描述：

  1α,4α-dihydroxy-cis-1,2,3,4,4a,5,8,8a-octahydronaphthalene 在 palladium on activated charcoal 吡啶 、 phosphate buffer 、 pig liver esterase 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 38.0 ℃ 、275.79 kPa 条件下， 反应 4.0h， 生成 (1R,4S,4aR,8aS)-4-[(methylsulfonyl)oxy]-decahydronaphthalen-1-yl acetate
  参考文献：
  名称：

  Enzymatic desymmetrization of meso-1α,4α-dihydroxy-cis-decalins

  摘要：

  The stereoselective acetylation of meso-decalindiols I and 2 by vinyl acetate in the presence of Candida antarctica lipase gave monoester (1R,4S,4aR,8aS)-5 and (1R,4S,4aR,8aS)-6 in high enantiomeric excess (ee greater than or equal to 98%). The hydrolysis of the corresponding meso-diacetates 3 and 4 in the presence of porcine liver esterase in phosphate buffer provided the opposite enantiomers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.004