(3S,1'R)-4-chloro-3-hydroxy-N-(1-phenylethyl)butanamide | 222311-40-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3S,1'R)-4-chloro-3-hydroxy-N-(1-phenylethyl)butanamide
• 英文别名: (3S)-4-chloro-3-hydroxy-N-[(1R)-1-phenylethyl]butanamide
• CAS: 222311-40-2
• 化学式: C₁₂H₁₆ClNO₂
• 分子量: 241.718
• InChiKey: KCSBNNMAUBCVTK-KOLCDFICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,1'R)-4-chloro-3-hydroxy-N-(1-phenylethyl)butanamide 在 咪唑 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (4S,1'R)-4-(tert-butyldimethylsilyloxy)-N-(1-phenylethyl)-2-oxopyrrolidine
  参考文献：
  名称：

  Candida antarctica Lipase-Catalyzed Doubly Enantioselective Aminolysis Reactions. Chemoenzymatic Synthesis of 3-Hydroxypyrrolidines and 4-(Silyloxy)-2-oxopyrrolidines with Two Stereogenic Centers

  摘要：

  Aminolyses of racemic and prochiral 3-hydroxyesters with racemic amines are effectively catalyzed by Candida antarctica lipase. In these processes, the simultaneous resolution of the ester and the amine, or the corresponding asymmetrization-resolution, takes place. In all cases, the high enantioselectivity shown by the lipase toward all the reactants allows the preparation of enantiopure 3-hydroxyamides with very high diastereomeric ratios. These 3-hydroxyamides are used as starting materials in the synthesis of 3-hydroxy- and 2-oxopyrrolidines, both containing two stereogenic centers in their structures.

  DOI：

  10.1021/jo981630a
• 作为产物：
  描述：

  DL-4-氯-3-羟基丁酸乙酯 、 α-苯乙胺 在 Candida antarctica lipase 、 4 Angstroems MS 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 (S)-(-)- α-甲基苄胺 、 (R)-(+)-4-氯-3-羟基丁酸乙酯 、 (3S,1'R)-4-chloro-3-hydroxy-N-(1-phenylethyl)butanamide 、 (3R,1'R)-4-chloro-3-hydroxy-N-(1-phenylethyl)butanamide
  参考文献：
  名称：

  Candida antarctica Lipase-Catalyzed Doubly Enantioselective Aminolysis Reactions. Chemoenzymatic Synthesis of 3-Hydroxypyrrolidines and 4-(Silyloxy)-2-oxopyrrolidines with Two Stereogenic Centers

  摘要：

  Aminolyses of racemic and prochiral 3-hydroxyesters with racemic amines are effectively catalyzed by Candida antarctica lipase. In these processes, the simultaneous resolution of the ester and the amine, or the corresponding asymmetrization-resolution, takes place. In all cases, the high enantioselectivity shown by the lipase toward all the reactants allows the preparation of enantiopure 3-hydroxyamides with very high diastereomeric ratios. These 3-hydroxyamides are used as starting materials in the synthesis of 3-hydroxy- and 2-oxopyrrolidines, both containing two stereogenic centers in their structures.

  DOI：

  10.1021/jo981630a