1-(benzyloxy)-4-(bromomethyl)azetidin-2-one

• 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: 1-(benzyloxy)-4-(bromomethyl)azetidin-2-one
• 英文别名: 4-(Bromomethyl)-1-phenylmethoxyazetidin-2-one；4-(bromomethyl)-1-phenylmethoxyazetidin-2-one
• 化学式: C₁₁H₁₂BrNO₂
• 分子量: 270.126
• InChiKey: HGFHIYSCQQUNES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(benzyloxy)-4-(bromomethyl)azetidin-2-one 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 sodium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 96.0h， 生成 N-((1-((1-(benzyloxy)-4-oxoazetidin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)benzamide
  参考文献：
  名称：

  Syntheses and studies of new forms of N-sulfonyloxy β-lactams as potential antibacterial agents and β-lactamase inhibitors

  摘要：

  The synthesis of a small library of N-sulfonyloxy-2-azetidinones is reported and the preliminary results of the investigation of the biological activity of these molecules are discussed. These new multi-electrophilic beta-lactams ('electrophilic bombs') display unexpected selectivity in their antibacterial activity and beta-lactamase inhibitory activity.[GRAPHICS](c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.08.005
• 作为产物：
  描述：

  溴甲苯 、 4-(溴甲基)-N-羟基-2-氮杂环丁酮 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以2 g的产率得到1-(benzyloxy)-4-(bromomethyl)azetidin-2-one
  参考文献：
  名称：

  Syntheses and studies of new forms of N-sulfonyloxy β-lactams as potential antibacterial agents and β-lactamase inhibitors

  摘要：

  The synthesis of a small library of N-sulfonyloxy-2-azetidinones is reported and the preliminary results of the investigation of the biological activity of these molecules are discussed. These new multi-electrophilic beta-lactams ('electrophilic bombs') display unexpected selectivity in their antibacterial activity and beta-lactamase inhibitory activity.[GRAPHICS](c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.08.005

文献信息

• PERIPHERALLY SUBSTITUTED MONOCYCLIC BETA-LACTAMS
  申请人：University of Notre Dame du Lac

  公开号：US20170355671A1

  公开（公告）日：2017-12-14

  The invention provides monobactams that can be used as antibacterial agents or intermediates for the preparation of other useful compounds such as antibacterial agents.

  这项发明提供了可以用作抗菌剂或其他有用化合物（如抗菌剂）制备的中间体的单环内酰胺。
• US9862680B2
  申请人：——

  公开号：US9862680B2

  公开（公告）日：2018-01-09
• Syntheses and studies of new forms of N-sulfonyloxy β-lactams as potential antibacterial agents and β-lactamase inhibitors
  作者：Serena Carosso、Marvin J. Miller

  DOI：10.1016/j.bmc.2015.08.005

  日期：2015.9

  The synthesis of a small library of N-sulfonyloxy-2-azetidinones is reported and the preliminary results of the investigation of the biological activity of these molecules are discussed. These new multi-electrophilic beta-lactams ('electrophilic bombs') display unexpected selectivity in their antibacterial activity and beta-lactamase inhibitory activity.[GRAPHICS](c) 2015 Elsevier Ltd. All rights reserved.