(3R,4S)-4-(4-Benzyloxy-phenyl)-3-[(S)-2-(4-fluoro-phenoxy)-1-hydroxy-ethyl]-1-(4-fluoro-phenyl)-azetidin-2-one | 182824-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R,4S)-4-(4-Benzyloxy-phenyl)-3-[(S)-2-(4-fluoro-phenoxy)-1-hydroxy-ethyl]-1-(4-fluoro-phenyl)-azetidin-2-one
• CAS: 182824-73-3
• 化学式: C₃₀H₂₅F₂NO₄
• 分子量: 501.53
• InChiKey: CASDPVAGRJJYLK-SSBOKUKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.69
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3R,4S)-4-(4-Benzyloxy-phenyl)-3-[(S)-2-(4-fluoro-phenoxy)-1-hydroxy-ethyl]-1-(4-fluoro-phenyl)-azetidin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 (3R,4S)-3-[(1S)-2-(4-fluorophenoxy)-1-hydroxyethyl]-1-(4-fluorophenyl)-4-(4-hydroxyphenyl)azetidin-2-one
  参考文献：
  名称：

  (−)-SCH 57939: synthesis and pharmacological properties of a potent, metabolically stable cholesterol absorption inhibitor

  摘要：

  Previous SAR studies of C-3 side chain modified analogs of (-)-SCH 48461,(1,3,4) as well as information concerning the metabolic stability this series, enabled us to design a cholesterol absorption inhibitor (i.e., (-) 2a, SCH 57939) with tenfold higher potency and greatly enhanced metabolic stability. The synthesis and pharmacological profile, including the role of relative stereochemistry at both the C3 and 1' positions in determining the SAR of these compounds, will be discussed. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00365-4
• 作为产物：
  描述：

  (Z)-1-(4-(benzyloxy)phenyl)-N-(4-fluorophenyl)methaneimine 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (3R,4S)-4-(4-Benzyloxy-phenyl)-3-[(S)-2-(4-fluoro-phenoxy)-1-hydroxy-ethyl]-1-(4-fluoro-phenyl)-azetidin-2-one
  参考文献：
  名称：

  (−)-SCH 57939: synthesis and pharmacological properties of a potent, metabolically stable cholesterol absorption inhibitor

  摘要：

  Previous SAR studies of C-3 side chain modified analogs of (-)-SCH 48461,(1,3,4) as well as information concerning the metabolic stability this series, enabled us to design a cholesterol absorption inhibitor (i.e., (-) 2a, SCH 57939) with tenfold higher potency and greatly enhanced metabolic stability. The synthesis and pharmacological profile, including the role of relative stereochemistry at both the C3 and 1' positions in determining the SAR of these compounds, will be discussed. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00365-4