(S)-1-(4-fluorophenyl)-4-(trifluoromethyl)azetidin-2-one | 1451061-31-6

• 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: (S)-1-(4-fluorophenyl)-4-(trifluoromethyl)azetidin-2-one
• 英文别名: (4S)-1-(4-Fluorophenyl)-4beta-(trifluoromethyl)azetidine-2-one；(4S)-1-(4-fluorophenyl)-4-(trifluoromethyl)azetidin-2-one
• CAS: 1451061-31-6
• 化学式: C₁₀H₇F₄NO
• 分子量: 233.165
• InChiKey: DAFNSRKXQNTXHL-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-碘-3-苯基丙烷 、 (S)-1-(4-fluorophenyl)-4-(trifluoromethyl)azetidin-2-one 在 lithium hexamethyldisilazane 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 以32%的产率得到(3R,4S)-1-(4-fluorophenyl)-3-(3-phenylpropyl)-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：

  (Z)-2,2,2-trifluoro-N-(4-fluorophenyl)acetimidoyl chloride 在 氯化亚砜 、 lithium hydroxide monohydrate 、 palladium on activated charcoal 、 甲基溴化镁 、 氢气 、 双氧水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 为溶剂， 反应 29.25h， 生成 (S)-1-(4-fluorophenyl)-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

文献信息

• An aza-Michael addition protocol to fluoroalkylated β-amino acid derivatives and enantiopure trifluoromethylated N-heterocycles
  作者：Xing Yang、Zhuo Chen、Yuan Cai、Yi-Yong Huang、Norio Shibata

  DOI：10.1039/c4gc01357c

  日期：——

  Aza-Michael addition under catalyst- and solvent-free conditions worked well to install various fluoroalkylated amino acid derivatives and three trifluoromethylated heterocycles.

  在无催化剂和溶剂的条件下，Aza-Michael加成反应成功地安装了各种氟烷基化氨基酸衍生物和三种三氟甲基杂环化合物。