4-(p-nitrophenoxy)azetidin-2-one | 31898-87-0

• 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: 4-(p-nitrophenoxy)azetidin-2-one
• 英文别名: 4-(4-nitro-phenoxy)-azetidin-2-one；4-(4-Nitrophenoxy)-azetidin-2-on；4-(4-Nitrophenoxy)azetidin-2-one
• CAS: 31898-87-0
• 化学式: C₉H₈N₂O₄
• 分子量: 208.174
• InChiKey: FZKCDUYSEXXUPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(p-nitrophenoxy)azetidin-2-one 在 sodium hydroxide 作用下， 生成 3H-Azet-2-one
  参考文献：
  名称：

  单环β-内酰胺碱促水解和甲醇分解的结构-反应性关系

  摘要：

  关系结构反应性倒甲醇 et l'hydrolyse basique de pres de 50 azetidinones substituees en position 1,3 et 4

  DOI：

  10.1021/ja00163a039
• 作为产物：
  描述：

  对硝基苯酚 、 4-乙酰氧基-2-氮杂环丁酮 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 12.0h， 以68%的产率得到4-(p-nitrophenoxy)azetidin-2-one
  参考文献：
  名称：

  Non-transpeptidase binding arylthioether β-lactams active against Mycobacterium tuberculosis and Moraxella catarrhalis

  摘要：

  The prevalence of drug resistance in both clinical and community settings as a consequence of alterations of biosynthetic pathways, enzymes or cell wall architecture is a persistent threat to human health. We have designed, synthesized, and tested a novel class of non-transpeptidase, beta-lactamase resistant monocyclic beta-lactams that carry an arylthio group at C4. These thioethers exhibit inhibitory and cidal activity against serine beta-lactamase producing Mycobacterium tuberculosis wild type strain (Mtb) and multiple (n = 8) beta-lactamase producing Moraxella catarrhalis clinical isolates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.025

文献信息

• Mechanism of the base-catalyzed elimination of para-substituted phenoxides from 4-(aryloxy)azetidin-2-ones
  作者：Leo R. Fedor

  DOI：10.1021/jo00200a015

  日期：1984.12
• Non-transpeptidase binding arylthioether β-lactams active against Mycobacterium tuberculosis and Moraxella catarrhalis
  作者：Tim N. Beck、Dina Lloyd、Rostislav Kuskovsky、Jeanette Minah、Kriti Arora、Balbina J. Plotkin、Jacalyn M. Green、Helena I. Boshoff、Clifton Barry、Jeffrey Deschamps、Monika I. Konaklieva

  DOI：10.1016/j.bmc.2014.11.025

  日期：2015.2

  The prevalence of drug resistance in both clinical and community settings as a consequence of alterations of biosynthetic pathways, enzymes or cell wall architecture is a persistent threat to human health. We have designed, synthesized, and tested a novel class of non-transpeptidase, beta-lactamase resistant monocyclic beta-lactams that carry an arylthio group at C4. These thioethers exhibit inhibitory and cidal activity against serine beta-lactamase producing Mycobacterium tuberculosis wild type strain (Mtb) and multiple (n = 8) beta-lactamase producing Moraxella catarrhalis clinical isolates. (C) 2014 Elsevier Ltd. All rights reserved.
• Structure-reactivity relationship for base-promoted hydrolysis and methanolysis of monocyclic .beta.-lactams
  作者：S. Nagaraja Rao、R. A. More O'Ferrall

  DOI：10.1021/ja00163a039

  日期：1990.3

  Relation structure reactivite pour la methanolyse et l'hydrolyse basique de pres de 50 azetidinones substituees en position 1,3 et 4

  关系结构反应性倒甲醇 et l'hydrolyse basique de pres de 50 azetidinones substituees en position 1,3 et 4