(3aR,5R,6aS)-methyl 5,6,6,6a-tetrachloro-1-oxohexahydro-1H-cyclopenta[c]furan-5-carboxylate | 1414878-50-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3aR,5R,6aS)-methyl 5,6,6,6a-tetrachloro-1-oxohexahydro-1H-cyclopenta[c]furan-5-carboxylate
• 英文别名: methyl (3aS,5R,6aR)-3a,4,4,5-tetrachloro-3-oxo-6,6a-dihydro-1H-cyclopenta[c]furan-5-carboxylate
• CAS: 1414878-50-4
• 化学式: C₉H₈Cl₄O₄
• 分子量: 321.972
• InChiKey: RTFDNAKCYHTPJV-VXFFBNABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1S,2R,4R)-(-)-2-endo-acetoxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene 在 sodium periodate 、 ruthenium(III) chloride trihydrate 、 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成 (3aR,5R,6aS)-methyl 5,6,6,6a-tetrachloro-1-oxohexahydro-1H-cyclopenta[c]furan-5-carboxylate 、 (1R,3S,4R)-dimethyl 4-(acetoxymethyl)-1,2,2,3-tetrachlorocyclopentane-1,3-dicarboxylate
  参考文献：
  名称：

  Stereoselective synthesis of γ-lactone fused cyclopentanoids

  摘要：

  The stereoselective synthesis of gamma-lactone fused cyclopentanoids applying chemoenzymatic methods is described. rac-2-Hydroxymethyl-1,4,5,6-tetrachloro-7,7-dimethoxybicyclo[2.2.1]hept-5-ene and rac-2-hydroxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene were successfully resolved by Candida rugosa lipase (CRL), to afford enantiomerically enriched products with an ee of 94 and 97%, respectively. The enantiomerically enriched acetates were then subjected to ruthenium and/or cerium catalyzed oxidation to afford alpha-diketones and subsequent alkaline H2O2 mediated oxidative cleavage reaction of alpha-diketones, followed by CH2N2 esterification, gave enantiomerically enriched gamma-lactone fused cyclopentanoids with known absolute configurations. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.09.010

文献信息

• Stereoselective synthesis of γ-lactone fused cyclopentanoids
  作者：Ayşegül Gümüş、Cihangir Tanyeli

  DOI：10.1016/j.tetasy.2012.09.010

  日期：2012.10

  The stereoselective synthesis of gamma-lactone fused cyclopentanoids applying chemoenzymatic methods is described. rac-2-Hydroxymethyl-1,4,5,6-tetrachloro-7,7-dimethoxybicyclo[2.2.1]hept-5-ene and rac-2-hydroxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene were successfully resolved by Candida rugosa lipase (CRL), to afford enantiomerically enriched products with an ee of 94 and 97%, respectively. The enantiomerically enriched acetates were then subjected to ruthenium and/or cerium catalyzed oxidation to afford alpha-diketones and subsequent alkaline H2O2 mediated oxidative cleavage reaction of alpha-diketones, followed by CH2N2 esterification, gave enantiomerically enriched gamma-lactone fused cyclopentanoids with known absolute configurations. (C) 2012 Elsevier Ltd. All rights reserved.