4-(2,4-dichlorobenzyloxy)-3-hydroxybutanenitrile | 922735-22-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2,4-dichlorobenzyloxy)-3-hydroxybutanenitrile
• 英文别名: 4-[(2,4-Dichlorophenyl)methoxy]-3-hydroxybutanenitrile；4-[(2,4-dichlorophenyl)methoxy]-3-hydroxybutanenitrile
• CAS: 922735-22-6
• 化学式: C₁₁H₁₁Cl₂NO₂
• 分子量: 260.12
• InChiKey: IYKHAWKQQZGKKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,4-dichlorobenzyloxy)-3-hydroxybutanenitrile 、 乙酸乙烯酯 在 Arthrobacter sp. lipase 作用下， 以 正庚烷 、 乙腈 为溶剂， 反应 70.0h， 以45%的产率得到(S)-4-(2,4-dichlorobenzyloxy)-3-hydroxybutanenitrile
  参考文献：
  名称：

  Efficient lipase-catalyzed kinetic resolution of 4-arylmethoxy-3-hydroxybutanenitriles: application to an expedient synthesis of a statin intermediate

  摘要：

  The kinetic resolution of 4-arylmethoxy-3-hydroxybutanenitriles was investigated by lipase-catalyzed transesterification in organic solvents. A high enantio selectivity was obtained via reaction with vinyl acetate in a mixed solvent (n-heptane/acetonitrile 1:1), which was catalyzed by the lipase from Artgribacter sp. A better selectivity was demonstrated when the number of substituents on the aryl ring increased. (S)-4-Arylmethoxy-3-hydroxybutanenitriles can be obtained with enantiomeric excesses of up to 98.0% by this method. Furthermore we have developed a novel route to synthesize tert-butyl (S)-6-benzyloxy-5-hydroxy-3-oxohexanoate, a key intermediate for the preparation of HMG-CoA reductase inhibitors (statins). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.037

文献信息

• Efficient lipase-catalyzed kinetic resolution of 4-arylmethoxy-3-hydroxybutanenitriles: application to an expedient synthesis of a statin intermediate
  作者：Fenglai Sun、Gang Xu、Jianping Wu、Lirong Yang

  DOI：10.1016/j.tetasy.2006.10.037

  日期：2006.11

  The kinetic resolution of 4-arylmethoxy-3-hydroxybutanenitriles was investigated by lipase-catalyzed transesterification in organic solvents. A high enantio selectivity was obtained via reaction with vinyl acetate in a mixed solvent (n-heptane/acetonitrile 1:1), which was catalyzed by the lipase from Artgribacter sp. A better selectivity was demonstrated when the number of substituents on the aryl ring increased. (S)-4-Arylmethoxy-3-hydroxybutanenitriles can be obtained with enantiomeric excesses of up to 98.0% by this method. Furthermore we have developed a novel route to synthesize tert-butyl (S)-6-benzyloxy-5-hydroxy-3-oxohexanoate, a key intermediate for the preparation of HMG-CoA reductase inhibitors (statins). (c) 2006 Elsevier Ltd. All rights reserved.