Methanesulfonic acid (1S,3aR,4S,6aR)-4-methanesulfonyloxy-octahydro-pentalen-1-yl ester | 193674-48-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Methanesulfonic acid (1S,3aR,4S,6aR)-4-methanesulfonyloxy-octahydro-pentalen-1-yl ester
• CAS: 193674-48-5
• 化学式: C₁₀H₁₈O₆S₂
• 分子量: 298.381
• InChiKey: XEIZNCDJXUWKFW-IMSYWVGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (1S,3aR,4S,6aR)-4-methanesulfonyloxy-octahydro-pentalen-1-yl ester 在 18-冠醚-6 、 Dowex 1x2-100 (OH^- form) 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 38.0h， 生成 (1R,2R,5R,6R)-bicyclo[3.3.0]octane-2,6-diol
  参考文献：
  名称：

  An improved procedure for the lipase-catalysed kinetic resolution of endo-endo-cis-bicyclo[3.3.0]octane-2,6-diol—synthesis of potential C2-symmetric enantiomerically pure bidentate auxiliaries

  摘要：

  An improved procedure for the kinetic resolution of endo-endo-cis-bicyclo[3.3.0]octane-2,6-diol rac-1 by transesterification with vinyl acetate catalysed by lipase from Pseudomonas cepacia in an organic solvent which yields both enantiomers with an enantiomeric excess of > 95% is described. The configuration at both stereogenic centres bearing hydroxy groups has been inverted by treatment of the corresponding mesylates with caesium acetate in the presence of 18-crown-6 to afford, after deacetylation, the corresponding enantiomerically pure diastereoisomeric exo-exo-cis-diols. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00213-9
• 作为产物：
  描述：

  endo,endo-cis-bicyclo[3.3.0]octane-2,6-diol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 Methanesulfonic acid (1S,3aR,4S,6aR)-4-methanesulfonyloxy-octahydro-pentalen-1-yl ester
  参考文献：
  名称：

  An improved procedure for the lipase-catalysed kinetic resolution of endo-endo-cis-bicyclo[3.3.0]octane-2,6-diol—synthesis of potential C2-symmetric enantiomerically pure bidentate auxiliaries

  摘要：

  An improved procedure for the kinetic resolution of endo-endo-cis-bicyclo[3.3.0]octane-2,6-diol rac-1 by transesterification with vinyl acetate catalysed by lipase from Pseudomonas cepacia in an organic solvent which yields both enantiomers with an enantiomeric excess of > 95% is described. The configuration at both stereogenic centres bearing hydroxy groups has been inverted by treatment of the corresponding mesylates with caesium acetate in the presence of 18-crown-6 to afford, after deacetylation, the corresponding enantiomerically pure diastereoisomeric exo-exo-cis-diols. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00213-9