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ethyl (2S,3R)-3-(4-chlorophenoxy)-2-hydroxybutanoate | 849704-25-2

中文名称
——
中文别名
——
英文名称
ethyl (2S,3R)-3-(4-chlorophenoxy)-2-hydroxybutanoate
英文别名
——
ethyl (2S,3R)-3-(4-chlorophenoxy)-2-hydroxybutanoate化学式
CAS
849704-25-2
化学式
C12H15ClO4
mdl
——
分子量
258.702
InChiKey
GZHSSDGHMRGGOG-KCJUWKMLSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    47-50 °C
  • 沸点:
    382.1±32.0 °C(Predicted)
  • 密度:
    1.233±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    2.6
  • 重原子数:
    17
  • 可旋转键数:
    6
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.42
  • 拓扑面积:
    55.8
  • 氢给体数:
    1
  • 氢受体数:
    4

反应信息

  • 作为产物:
    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
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文献信息

  • 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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