(3aR,6aR)-2,5-Dihydroxy-3,3a,6,6a-tetrahydro-pentalene-1,4-dicarboxylic acid dimethyl ester | 163512-89-8

• 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: (3aR,6aR)-2,5-Dihydroxy-3,3a,6,6a-tetrahydro-pentalene-1,4-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl (3aR,6aR)-2,5-dihydroxy-3,3a,6,6a-tetrahydropentalene-1,4-dicarboxylate
• CAS: 163512-89-8
• 化学式: C₁₂H₁₄O₆
• 分子量: 254.24
• InChiKey: PYJGYFRREXXUPB-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  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 、 三氟甲磺酸三甲基硅酯 、 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 42.58h， 生成
  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：

  (1S,3R,3aR,4S,6R,6aR)-2,5-Dioxo-octahydro-pentalene-1,3,4,6-tetracarboxylic acid tetramethyl ester 在 phosphate buffer 、 lipase M Amano 作用下， 以 甲苯 为溶剂， 反应 168.0h， 生成 (3aR,6aR)-2,5-Dihydroxy-3,3a,6,6a-tetrahydro-pentalene-1,4-dicarboxylic acid dimethyl ester 、 dimethyl (3aS,6aS)-2,5-dihydroxy-3,3a,6,6a-tetrahydropentalene-1,4-dicarboxylate
  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

• An asymmetric synthesis of C2-symmetric dimethyl 3,7-dioxo-cis-bicyclo[3.3.0]octane-2,6-dicarboxylate by lipase-catalyzed demethoxycarbonylation
  作者：Manabu Node、Takehisa Inoue、Mamoru Araki、Daisaku Nakamura、Kiyoharu Nishide

  DOI：10.1016/0040-4039(95)00264-d

  日期：1995.3

  Both enantiomers of C2-symmetric dimethyl 3,7-dioxo-cis-bicyclo[3.3.0]-octane-2,6-dicarboxylate (3) were prepared in enantiomerically pure form by the lipase-catalyzed demethoxycarbonylation, respectively. An expeditious formal total synthesis of (+)-carbacyclin using this hybrid process was done.

  的两种对映体c ^ 2 -对称二甲基-3,7-二氧代-顺-二环[3.3.0] -辛烷-2,6-二羧酸二（3）在对映体纯形式制备分别由脂酶催化demethoxycarbonylation。使用此混合过程可快速完成（+）-碳环素的正式全合成。
• LANNOYE, G.;SAMBASIVARAO, KOTHA;WEHRLI, S.;COOK, J. M.;WEISS, U., J. ORG. CHEM., 53,(1988) N 10, 2327-2340
  作者：LANNOYE, G.、SAMBASIVARAO, KOTHA、WEHRLI, S.、COOK, J. M.、WEISS, U.

  DOI：——

  日期：——
• 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.