(3S,4S)-3-((1S,2S)-2-Azido-1-hydroxy-butyl)-3-bromo-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one | 917110-41-9

• 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: (3S,4S)-3-((1S,2S)-2-Azido-1-hydroxy-butyl)-3-bromo-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one
• 英文别名: (3S,4S)-3-[(1S,2S)-2-azido-1-hydroxybutyl]-3-bromo-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one
• CAS: 917110-41-9
• 化学式: C₂₁H₂₃BrN₄O₂
• 分子量: 443.343
• InChiKey: UAPYDHGDPWJEET-LJZWMIMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-((1S,2S)-2-Azido-1-hydroxy-butyl)-3-bromo-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one 在 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2S,3R,6S)-2-((S)-1-Azido-propyl)-6-phenyl-5-((S)-1-phenyl-ethyl)-1-oxa-5-aza-spiro[2.3]hexan-4-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Azido- and Aziridino-hydroxyl-β-lactams through Stereo- and Regioselective Epoxide Ring Opening

  摘要：

  [GRAPHICS]Two new classes of azido- and aziridino-hydroxyl-beta-lactam containing structures have been prepared by means of a stereo- and regioselective epoxide ring opening. The straightforwardness of the procedure makes this strategy useful for the synthesis of potentially bioactive compounds. Some selected examples showed promising activity in acyl CoA-cholesterol acyltransferase inhibition assays.

  DOI：

  10.1021/jo0615652
• 作为产物：
  描述：

  (1S',3R,4S)-3-bromo-3-but-1-enyl-4-phenyl-1-(1-phenylethyl)azetidin-2-one 在 sodium azide 、 二甲基氯化铝 、 间氯过氧苯甲酸 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 生成 (3S,4S)-3-((1S,2S)-2-Azido-1-hydroxy-butyl)-3-bromo-4-phenyl-1-((S)-1-phenyl-ethyl)-azetidin-2-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Azido- and Aziridino-hydroxyl-β-lactams through Stereo- and Regioselective Epoxide Ring Opening

  摘要：

  [GRAPHICS]Two new classes of azido- and aziridino-hydroxyl-beta-lactam containing structures have been prepared by means of a stereo- and regioselective epoxide ring opening. The straightforwardness of the procedure makes this strategy useful for the synthesis of potentially bioactive compounds. Some selected examples showed promising activity in acyl CoA-cholesterol acyltransferase inhibition assays.

  DOI：

  10.1021/jo0615652

文献信息

• Synthesis and Biological Evaluation of Azido- and Aziridino-hydroxyl-β-lactams through Stereo- and Regioselective Epoxide Ring Opening
  作者：Fides Benfatti、Giuliana Cardillo、Luca Gentilucci、Rossana Perciaccante、Alessandra Tolomelli、Alberico Catapano

  DOI：10.1021/jo0615652

  日期：2006.11.1

  [GRAPHICS]Two new classes of azido- and aziridino-hydroxyl-beta-lactam containing structures have been prepared by means of a stereo- and regioselective epoxide ring opening. The straightforwardness of the procedure makes this strategy useful for the synthesis of potentially bioactive compounds. Some selected examples showed promising activity in acyl CoA-cholesterol acyltransferase inhibition assays.