ethyl (2S,3R)-2-chloro-3-hydroxybutanoate | 150131-74-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl (2S,3R)-2-chloro-3-hydroxybutanoate
• 英文别名: ethyl 2-chloro-3-hydroxybutyrate
• CAS: 150131-74-1
• 化学式: C₆H₁₁ClO₃
• 分子量: 166.605
• InChiKey: XWWGVYVLALKWDS-UHNVWZDZSA-N

物化性质

• 沸点：
  245.1±20.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (2S,3R)-2-chloro-3-hydroxybutanoate 、 caesium 4-chlorophenate 反应 120.0h， 以5%的产率得到ethyl (2R,3R)-2-(4-chlorophenoxy)-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：

  碘乙烷 、 (2S,3R)-2-chloro-3-hydroxybutanoic acid 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57%的产率得到ethyl (2S,3R)-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

文献信息

• A recombinant ketoreductase tool-box. Assessing the substrate selectivity and stereoselectivity toward the reduction of β-ketoesters
  作者：Dunming Zhu、Chandrani Mukherjee、J. David Rozzell、Spiros Kambourakis、Ling Hua

  DOI：10.1016/j.tet.2005.10.044

  日期：2006.1

  The substrate selectivity and stereoselectivity of a series of ketoreductases were evaluated toward the reduction of two sets of beta-ketoesters. Both the structural variety at beta-position and the substituent at alpha-position greatly affected the activity and stereoselectivity of these ketoreductases. For the first set of beta-ketoesters, at least one ketoreductase was found that catalyzed the formation of either (D) or (L) enantiomer of beta-hydroxyesters from each substrate with high optical purity, with the only exception of ethyl (D)-3-hydroxy3-phenylpropionate. For the second set of beta-ketoesters with alpha-substituents, the situation is more complex. More commonly, a ketoreductase was found that formed one of the four diastereomers in optically pure form, with only a few cases in which enzymes could be found that formed two or more of the diastereomers in high optical purity. The continued development of new, more diverse ketoreductases will create the capability to produce a wider range of single diastereomers of 2-substituted-3-hydroxy acids and their derivatives. (c) 2005 Elsevier Ltd. All rights reserved.
• A new enantioselective synthesis of glycidates via dynamic kinetic resolution of racemic 2-chloro-3-keto esters using chiral Ru (II) complexes
  作者：Jean-Pierre Genêt、M.C. Caño de Andrade、V. Ratovelomanana-Vidal

  DOI：10.1016/0040-4039(95)00182-c

  日期：1995.3

  2-chloro-3-keto esters were quantitatively hydrogenated to syn and anti 2-chloro-3-hydroxyester by asymmetric hydrogenation with chiral ruthenium (Ii) catalysts prepared in-situ from (COD)Ru(2-Methylallyl)(2) in presence of atropisomeric ligands such as MeO-Biphep and Binap, giving enantioselectivity up to 99%. 2-chloro-3-hydroxy esters were treated with different bases to give (E)- and (Z)-2,3-epoxyalkanoates in 65-90% yields with 84-97% ee.
• The microbial reduction of 2-chloro-3-oxoesters
  作者：Odile Cabon、Didier Buisson、Marc Larcheveque、Robert Azerad

  DOI：10.1016/0957-4166(95)00294-y

  日期：1995.9

  Several aliphatic or aromatic 2-chloro-3-oxoesters are stereoselectively reduced by yeast or fungal strains, affording in fair to good yield and high enantiomeric excess some of the respective 2-chloro-3-hydroxyester stereoisomers.
• 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.