(S)-methyl 4,4,4-trifluoro-3-(4-methoxyphenylamino)butanoate | 1453252-00-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-methyl 4,4,4-trifluoro-3-(4-methoxyphenylamino)butanoate
• 英文别名: methyl (3S)-4,4,4-trifluoro-3-(4-methoxyanilino)butanoate
• CAS: 1453252-00-0
• 化学式: C₁₂H₁₄F₃NO₃
• 分子量: 277.243
• InChiKey: NCVMMHKQRHAKDH-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 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：
  47.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  N-(4-Methoxyphenyl)trifluoroacetimidoyl Chloride 在 氯化亚砜 、 lithium hydroxide monohydrate 、 palladium on activated charcoal 、 氢气 、 双氧水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 28.5h， 生成 (S)-methyl 4,4,4-trifluoro-3-(4-methoxyphenylamino)butanoate
  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