(1S,2R,4R)-(-)-2-endo-acetoxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene | 863642-00-6

• 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: (1S,2R,4R)-(-)-2-endo-acetoxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene
• 英文别名: ((1S,2R,4R)-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-en-2-yl)methyl acetate；[(1S,2R,4R)-1,4,5,6,7,7-hexachloro-2-bicyclo[2.2.1]hept-5-enyl]methyl acetate
• CAS: 863642-00-6
• 化学式: C₁₀H₈Cl₆O₂
• 分子量: 372.89
• InChiKey: NDRFJTDXRVUIET-CGMLFGJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  二环[2.2.1]庚-5-烯-2-甲醇,1,4,5,6,7,7-六氯-,内- 在 吡啶 、 horse liver acetone 作用下， 以 phosphate buffer 、 二氯甲烷 为溶剂， 反应 37.0h， 生成 (1S,2R,4R)-(-)-2-endo-acetoxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene
  参考文献：
  名称：

  Enzymatic resolution of (±)-2-endo-hydroxymethyl and acetoxymethyl substituted hexachloronorbornene derivatives

  摘要：

  (±)-2-endo-羟甲基-1,4,5,6,7,7-六氯双环[2.2.1]庚-5-烯及其(±)-2-endo-乙酰氧甲基衍生物通过使用各种水解酶进行分解，得到光学纯度高达94%-98%的对映体富集产物。绝对构型通过将2-endo-乙酰氧甲基-1,4,5,6,7,7-六氯双环[2.2.1]庚-5-烯转化为已知绝对构型的2-endo-羟甲基双环[2.2.1]庚-5-烯来确定。© 2005 Elsevier Ltd. 保留所有权利。

  DOI：

  10.1016/j.tetasy.2005.06.014