(1R,2S,4S)-(+)-2-endo-hydroxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (1R,2S,4S)-(+)-2-endo-hydroxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene
• 英文别名: ((1R,2S,4S)-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-en-2-yl)methanol；[(1R,2S,4S)-1,4,5,6,7,7-hexachloro-2-bicyclo[2.2.1]hept-5-enyl]methanol
• 化学式: C₈H₆Cl₆O
• 分子量: 330.853
• InChiKey: JFSYHGUBAXUJEV-DKPVMLCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  六氯环戊二烯 在 candidapepsin 、 对苯二酚 作用下， 反应 172.0h， 生成 (1R,2S,4S)-(+)-2-endo-hydroxymethyl-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

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.
• Enzymatic resolution of (±)-2-endo-hydroxymethyl and acetoxymethyl substituted hexachloronorbornene derivatives
  作者：Yunus Emre Türkmen、İdris Mecidoğlu Akhmedov、Cihangir Tanyeli

  DOI：10.1016/j.tetasy.2005.06.014

  日期：2005.7

  (+/-)-2-endo-Hydroxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene and (+/-)-2-endo-acetoxymethyl-1,4,5,6,7,7hexachlorobicyclo[2.2.1]hept-5-ene were resolved by using various hydrolases to afford enantiomerically enriched products with ees of 94-98%. The absolute configuration was determined by transforming 2-endo-acetoxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene into 2-endo-hydroxymetliyl-bicyclo[2.2.1]hept-5-ene with known absolute configuration. (c) 2005 Elsevier Ltd. All rights reserved.

  (±)-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。