(3R,4S)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-1-(4-methoxyphenyl)-4(trifluoromethyl)azetidin-2-one | 1451061-25-8

• 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)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-1-(4-methoxyphenyl)-4(trifluoromethyl)azetidin-2-one
• 英文别名: (3R,4S)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-1-(4-methoxyphenyl)-4-(trifluoromethyl)azetidin-2-one
• CAS: 1451061-25-8
• 化学式: C₂₀H₁₉F₄NO₃
• 分子量: 397.369
• InChiKey: UFGQHZYUCUVEAI-SQNIBIBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (S)-methyl 4,4,4-trifluoro-3-(4-methoxyphenylamino)butanoate 在 吡啶 、 甲基溴化镁 、 氟化氢吡啶 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 21.75h， 生成 (3R,4S)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-1-(4-methoxyphenyl)-4(trifluoromethyl)azetidin-2-one
  参考文献：
  名称：

  4-CF3-ezetimibe analogs: design, synthesis, and biological evaluation of cholesterol absorption inhibitions

  摘要：

  On the purpose of looking for better cholesterol absorption inhibitors, several trifluoromethyl substituted ezetimibe analogs 1a-d were designed and synthesized. The key steps in the synthesis of these optically pure trans-4-CF3-beta-lactams include chiral auxiliary induced asymmetric hydrogenation and substrate controlled stereoselective alkylation. The inhibitory activities of these target compounds were evaluated on the cholesterol absorption in Caco-2 cells. The result showed that the inhibitory activity of compound 1a was comparable to ezetimibe. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.027