(1R,2R,5R,6R)-bicyclo[3.3.0]octane-2,6-diyl diacetate | 193810-58-1

• 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,2R,5R,6R)-bicyclo[3.3.0]octane-2,6-diyl diacetate
• 英文别名: [(1R,3aR,4R,6aR)-4-acetyloxy-1,2,3,3a,4,5,6,6a-octahydropentalen-1-yl] acetate
• CAS: 193810-58-1
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: HYVIARUUVHVLHF-DDHJBXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,5R,6R)-bicyclo[3.3.0]octane-2,6-diyl diacetate 在 Dowex 1x2-100 (OH^- form) 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以99%的产率得到(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：

  (1R,2S,5R,6S)-bicyclo[3.3.0]octane-2,6-diol 在 吡啶 、 18-冠醚-6 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.0h， 生成 (1R,2R,5R,6R)-bicyclo[3.3.0]octane-2,6-diyl diacetate
  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