(1S,2S,3aS,6aR)-2-Hydroxy-5-oxo-octahydro-pentalene-1-carboxylic acid methyl ester | 204515-17-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (1S,2S,3aS,6aR)-2-Hydroxy-5-oxo-octahydro-pentalene-1-carboxylic acid methyl ester
• 英文别名: methyl (1S,2S,3aS,6aR)-2-hydroxy-5-oxo-2,3,3a,4,6,6a-hexahydro-1H-pentalene-1-carboxylate
• CAS: 204515-17-3
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: YEEDMQFXOCMPFJ-ZLNHGNLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,3aS,6aR)-2-Hydroxy-5-oxo-octahydro-pentalene-1-carboxylic acid methyl ester 在 吡啶 、 咪唑 、 lithium aluminium tetrahydride 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 50.58h， 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
• 作为产物：
  描述：

  (3aR,6aR)-2,5-Dihydroxy-3,3a,6,6a-tetrahydro-pentalene-1,4-dicarboxylic acid dimethyl ester 在 盐酸 、 lithium hydroxide 、 sodium triethoxyborohydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 20.0h， 生成 (1S,2S,3aS,6aR)-2-Hydroxy-5-oxo-octahydro-pentalene-1-carboxylic acid methyl ester
  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.