(1R,2S,3S,5S)-7,7-ethylenedioxy-3-hydroxy-2-methylbicyclo[3.3.0]octane | 204515-14-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,3S,5S)-7,7-ethylenedioxy-3-hydroxy-2-methylbicyclo[3.3.0]octane
• 英文别名: (1'S,2'S,3'aS,6'aR)-1'-methylspiro[1,3-dioxolane-2,5'-2,3,3a,4,6,6a-hexahydro-1H-pentalene]-2'-ol
• CAS: 204515-14-0
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: ICBFNEWCWKQFMZ-XKNYDFJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,5S)-7,7-ethylenedioxy-3-hydroxy-2-methylbicyclo[3.3.0]octane 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以70%的产率得到(1R,2S,5S)-7,7-ethylenedioxy-2-methylbicyclo[3.3.0]octan-3-one
  参考文献：
  名称：

  Lipase-catalyzed asymmetric demethoxycarbonylation: Formal syntheses of (+)-carbacyclin, (−)-ajmalicine, and (−)-tetrahydroalstonine

  摘要：

  Both enantiomers of C-2-symmetric dimethyl 3,7-dihydroxybicyclo[3.3.0]-octa-2,6-dicarboxylate 3 were prepared in enantiomerically pure form from symmetric tetraester 1 by the lipase-catalyzed demethoxycarbonylation, respectively. Double asymmetric differentiation with lipase in the above demethoxycarbonylation was observed. Their applications to formal total syntheses of (+)-carbacyclin and (-)-ajmalicine including (-)-tetrahydroalstonine are also described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00616-2
• 作为产物：
  描述：

  (3aR,6aR)-2,5-Dihydroxy-3,3a,6,6a-tetrahydro-pentalene-1,4-dicarboxylic acid dimethyl ester 在 吡啶 、 咪唑 、 盐酸 、 lithium hydroxide 、 lithium aluminium tetrahydride 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 sodium triethoxyborohydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 70.58h， 生成 (1R,2S,3S,5S)-7,7-ethylenedioxy-3-hydroxy-2-methylbicyclo[3.3.0]octane
  参考文献：
  名称：

  Lipase-catalyzed asymmetric demethoxycarbonylation: Formal syntheses of (+)-carbacyclin, (−)-ajmalicine, and (−)-tetrahydroalstonine

  摘要：

  Both enantiomers of C-2-symmetric dimethyl 3,7-dihydroxybicyclo[3.3.0]-octa-2,6-dicarboxylate 3 were prepared in enantiomerically pure form from symmetric tetraester 1 by the lipase-catalyzed demethoxycarbonylation, respectively. Double asymmetric differentiation with lipase in the above demethoxycarbonylation was observed. Their applications to formal total syntheses of (+)-carbacyclin and (-)-ajmalicine including (-)-tetrahydroalstonine are also described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00616-2

文献信息

• Lipase-catalyzed asymmetric demethoxycarbonylation: Formal syntheses of (+)-carbacyclin, (−)-ajmalicine, and (−)-tetrahydroalstonine
  作者：Manabu Node、Takehisa Inoue、Mamoru Araki、Daisaku Nakamura、Kiyoharu Nishide

  DOI：10.1016/s0957-4166(97)00616-2

  日期：1998.1

  Both enantiomers of C-2-symmetric dimethyl 3,7-dihydroxybicyclo[3.3.0]-octa-2,6-dicarboxylate 3 were prepared in enantiomerically pure form from symmetric tetraester 1 by the lipase-catalyzed demethoxycarbonylation, respectively. Double asymmetric differentiation with lipase in the above demethoxycarbonylation was observed. Their applications to formal total syntheses of (+)-carbacyclin and (-)-ajmalicine including (-)-tetrahydroalstonine are also described. (C) 1998 Elsevier Science Ltd. All rights reserved.