(2S,3S)-2-chloro-3-hydroxybutanoic acid | 36977-29-4

• 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: (2S,3S)-2-chloro-3-hydroxybutanoic acid
• CAS: 36977-29-4
• 化学式: C₄H₇ClO₃
• 分子量: 138.551
• InChiKey: QTQIANGQRHQQJU-HRFVKAFMSA-N

物化性质

• 沸点：
  276.6±25.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-chloro-3-hydroxybutanoic acid 、 碘乙烷 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 以64%的产率得到ethyl (2S,3S)-2-chloro-3-hydroxybutanoate
  参考文献：
  名称：

  Reaction of caesium 4-chlorophenate and chlorohydrins from threonines: synthesis of clofibrate analogues

  摘要：

  Clofibrate is a well-known peroxisome prolifierator-activated receptor-alpha (PPARalpha) agonist, used in the treatment of hyperlipaemias and atherosclerosis and to prevent heart failure. Herein, the preparation of the four enantiomerically pure stereoisomers of ethyl 2-(4-chlorophenoxy)-3-hydroxybutanoate as clofibrate analogues is described. Biological evaluation of these new compounds was performed by a transactivation assay in a transiently transfected monkey kidney fibroblast cell line. All four diastereomers were inactive even at 300 muM, where clofibrate showed an evident activity, suggesting that the designed clofibrate molecular structural modifications in the analogues caused the loss of peroxisome proliferator-activated receptor-alpha (PPARalpha) activity. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.006
• 作为产物：
  描述：

  L-别苏氨酸 在 盐酸 、 sodium nitrite 作用下， 反应 5.0h， 以87%的产率得到(2S,3S)-2-chloro-3-hydroxybutanoic acid
  参考文献：
  名称：

  Reaction of caesium 4-chlorophenate and chlorohydrins from threonines: synthesis of clofibrate analogues

  摘要：

  Clofibrate is a well-known peroxisome prolifierator-activated receptor-alpha (PPARalpha) agonist, used in the treatment of hyperlipaemias and atherosclerosis and to prevent heart failure. Herein, the preparation of the four enantiomerically pure stereoisomers of ethyl 2-(4-chlorophenoxy)-3-hydroxybutanoate as clofibrate analogues is described. Biological evaluation of these new compounds was performed by a transactivation assay in a transiently transfected monkey kidney fibroblast cell line. All four diastereomers were inactive even at 300 muM, where clofibrate showed an evident activity, suggesting that the designed clofibrate molecular structural modifications in the analogues caused the loss of peroxisome proliferator-activated receptor-alpha (PPARalpha) activity. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.006

文献信息

• Access to (S)-2-methyloxetane and the precursor (S)-1,3-butanediol of high enantiomeric purity
  作者：Klaus Hintzer、Bernhard Koppenhoefer、Volker Schurig

  DOI：10.1021/jo00141a009

  日期：1982.9
• Reaction of caesium 4-chlorophenate and chlorohydrins from threonines: synthesis of clofibrate analogues
  作者：Maria Grazia Perrone、Ernesto Santandrea、Leonardo Di Nunno、Antonio Scilimati、Vincenzo Tortorella、Francesco Capitelli、Valerio Bertolasi

  DOI：10.1016/j.tetasy.2005.01.006

  日期：2005.2

  Clofibrate is a well-known peroxisome prolifierator-activated receptor-alpha (PPARalpha) agonist, used in the treatment of hyperlipaemias and atherosclerosis and to prevent heart failure. Herein, the preparation of the four enantiomerically pure stereoisomers of ethyl 2-(4-chlorophenoxy)-3-hydroxybutanoate as clofibrate analogues is described. Biological evaluation of these new compounds was performed by a transactivation assay in a transiently transfected monkey kidney fibroblast cell line. All four diastereomers were inactive even at 300 muM, where clofibrate showed an evident activity, suggesting that the designed clofibrate molecular structural modifications in the analogues caused the loss of peroxisome proliferator-activated receptor-alpha (PPARalpha) activity. (C) 2005 Elsevier Ltd. All rights reserved.

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