(S)-4-chloro-3-hydroxybutanamide | 175158-38-0

• 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: (S)-4-chloro-3-hydroxybutanamide
• 英文别名: (S)-4-chloro-3-hydroxybutyramide；(3S)-4-chloro-3-hydroxybutyrylamide；(3S)-4-chloro-3-hydroxybutanamide
• CAS: 175158-38-0
• 化学式: C₄H₈ClNO₂
• 分子量: 137.566
• InChiKey: NWQXZIZIZSQPHR-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-4-chloro-3-hydroxybutanamide 在 ammonium hydroxide 、 Amberlite IRA-120B (H⁺) 作用下， 反应 18.0h， 以80%的产率得到(S)-(+)-4-氨基-3-羟基丁酸
  参考文献：
  名称：

  Efficient Syntheses of (S)-4-Hydroxy-2-pyrrolidinone Derivatives

  摘要：

  Efficient syntheses of (S)-4-hydroxy-2-pyrrolidinone ((S)-2) and (R)-4-acetylthio-2-pyrrolidinone (5), which are key intermediates of oral carbapenem CS-834, were studied. The most efficient route to (S)-2 from (S)-3-hydroxybutyrolactone (8) was accomplished in high yield via (S)-N-allyl-3-(1-ethoxy)ethoxy-4-hydroxybutyramide (14).

  DOI：

  10.3987/com-99-8689
• 作为产物：
  描述：

  (S)-4-氯-3-羟基丁腈 在 双氧水 、 sodium hydroxide 作用下， 反应 3.0h， 以55%的产率得到(S)-4-chloro-3-hydroxybutanamide
  参考文献：
  名称：

  Efficient Syntheses of (S)-4-Hydroxy-2-pyrrolidinone Derivatives

  摘要：

  Efficient syntheses of (S)-4-hydroxy-2-pyrrolidinone ((S)-2) and (R)-4-acetylthio-2-pyrrolidinone (5), which are key intermediates of oral carbapenem CS-834, were studied. The most efficient route to (S)-2 from (S)-3-hydroxybutyrolactone (8) was accomplished in high yield via (S)-N-allyl-3-(1-ethoxy)ethoxy-4-hydroxybutyramide (14).

  DOI：

  10.3987/com-99-8689

文献信息

• Enzymatic ammonolysis of ethyl (±)-4-chloro-3-hydroxybutanoate. Chemoenzymatic syntheses of both enantiomers of pyrrolidin-3-ol and 5-(chloromethyl)-1,3-oxazolidin-2-one
  作者：Eduardo Garcı́a-Urdiales、Francisca Rebolledo、Vicente Gotor

  DOI：10.1016/s0957-4166(99)00034-8

  日期：1999.2

  Lipase B from Candida antarctica efficiently catalysed the kinetic resolution of ethyl (+/-)-4-chloro-3-hydroxybutanoate through an ammonolysis reaction. Using this methodology, both enantiomers of 4-chloro-3-hydroxybutanamide were prepared and converted into pyrrolidin-3-ol and 5-(chloromethyl)-1,3-oxazolidin-2-one by simple processes consisting of a reduction reaction and a Hofmann rearrangement, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Efficient Syntheses of (S)-4-Hydroxy-2-pyrrolidinone Derivatives
  作者：Osamu Kanno、Masao Miyauchi、Isao Kawamoto

  DOI：10.3987/com-99-8689

  日期：——

  Efficient syntheses of (S)-4-hydroxy-2-pyrrolidinone ((S)-2) and (R)-4-acetylthio-2-pyrrolidinone (5), which are key intermediates of oral carbapenem CS-834, were studied. The most efficient route to (S)-2 from (S)-3-hydroxybutyrolactone (8) was accomplished in high yield via (S)-N-allyl-3-(1-ethoxy)ethoxy-4-hydroxybutyramide (14).