(3S,1'R)-4-chloro-N-<1-(2-furyl)ethyl>3-hydroxybutanamide | 222311-41-3

• 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-N-<1-(2-furyl)ethyl>3-hydroxybutanamide
• 英文别名: (3S)-4-chloro-N-[(1R)-1-(furan-2-yl)ethyl]-3-hydroxybutanamide
• CAS: 222311-41-3
• 化学式: C₁₀H₁₄ClNO₃
• 分子量: 231.679
• InChiKey: RGYPIYJDIGFORB-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,1'R)-4-chloro-N-<1-(2-furyl)ethyl>3-hydroxybutanamide 在 咪唑 、 4-二甲氨基吡啶 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (4S,1'R)-4-(tert-butyldimethylsilyloxy)-N-<1-(2-furyl)ethyl>-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：

  [1,2,4]三唑-1-基乙酸 、 DL-4-氯-3-羟基丁酸乙酯 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 (R)-(+)-4-氯-3-羟基丁酸乙酯 、 (S)-1-(furan-2-yl)ethanamine 、 (3S,1'R)-4-chloro-N-<1-(2-furyl)ethyl>3-hydroxybutanamide 、 (3R,1'R)-4-chloro-N-<1-(2-furyl)ethyl>3-hydroxybutanamide
  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

文献信息

• <i>Candida </i><i>a</i><i>ntarctica</i> Lipase-Catalyzed Doubly Enantioselective Aminolysis Reactions. Chemoenzymatic Synthesis of 3-Hydroxypyrrolidines and 4-(Silyloxy)-2-oxopyrrolidines with Two Stereogenic Centers
  作者：Víctor M. Sánchez、Francisca Rebolledo、Vicente Gotor

  DOI：10.1021/jo981630a

  日期：1999.3.1

  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.