((1S,2R,4R)-1,4,7,7-tetrachloro-5,6-dioxobicyclo[2.2.1]heptan-2-yl)methyl acetate | 1414878-57-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((1S,2R,4R)-1,4,7,7-tetrachloro-5,6-dioxobicyclo[2.2.1]heptan-2-yl)methyl acetate
• 英文别名: [(1S,2R,4R)-1,4,7,7-tetrachloro-5,6-dioxo-2-bicyclo[2.2.1]heptanyl]methyl acetate
• CAS: 1414878-57-1
• 化学式: C₁₀H₈Cl₄O₄
• 分子量: 333.983
• InChiKey: XJRCAFAJSYSAPB-CGMLFGJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((1S,2R,4R)-1,4,7,7-tetrachloro-5,6-dioxobicyclo[2.2.1]heptan-2-yl)methyl acetate 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 、
  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
• 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 作用下， 以 水 、 乙腈 为溶剂， 以90%的产率得到((1S,2R,4R)-1,4,7,7-tetrachloro-5,6-dioxobicyclo[2.2.1]heptan-2-yl)methyl acetate
  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