(1R,4S,4aR,8aS)-4-hydroxy-1,2,3,4,4a,8,8a-octahydronaphthalen-1-yl acetate | 821788-44-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,4S,4aR,8aS)-4-hydroxy-1,2,3,4,4a,8,8a-octahydronaphthalen-1-yl acetate
• 英文别名: [(1R,4S,4aR,8aS)-4-hydroxy-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl] acetate
• CAS: 821788-44-7
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: SXQQWLOWHVHYLY-NOOOWODRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4S,4aR,8aS)-4-hydroxy-1,2,3,4,4a,8,8a-octahydronaphthalen-1-yl acetate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 生成 (1R,4S,4aR,8aS)-4-hydroxy-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
• 作为产物：
  描述：

  1α,4α-dihydroxy-cis-1,2,3,4,4a,5,8,8a-octahydronaphthalene 在 吡啶 、 phosphate buffer 、 pig liver esterase 作用下， 生成 (1R,4S,4aR,8aS)-4-hydroxy-1,2,3,4,4a,8,8a-octahydronaphthalen-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