3-(2,4-dichlorophenoxy)-1-(4-methoxyphenyl)-4-(4-nitro-phenyl)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: 3-(2,4-dichlorophenoxy)-1-(4-methoxyphenyl)-4-(4-nitro-phenyl)azetidin-2-one
• 英文别名: (3S,4R)-3-(2,4-dichlorophenoxy)-1-(4-methoxyphenyl)-4-(4-nitrophenyl)azetidin-2-one
• 化学式: C₂₂H₁₆Cl₂N₂O₅
• 分子量: 459.285
• InChiKey: NPWYKNQIPGRGBL-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  84.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2,4-dichlorophenoxy)-1-(4-methoxyphenyl)-4-(4-nitro-phenyl)azetidin-2-one 在 乙醇 、 iron oxide 、 sodium hydroxide 作用下， 反应 1.5h， 以95%的产率得到
  参考文献：
  名称：

  Application of magnetic Fe₃O₄nanoparticles as a reusable heterogeneous catalyst in the synthesis of β-lactams containing amino groups

  摘要：

  磁性Fe3O4纳米颗粒在乙醇中促进含硝基芳基的β-内酰胺类化合物还原为含氨基芳基的β-内酰胺类化合物的催化活性被报道。这种方法方便且环保。

  DOI：

  10.1039/c9nj02759a
• 作为产物：
  描述：

  N-(4-甲氧基苯基)-1-(4-硝基苯基)甲亚胺 、 2,4-二氯苯氧乙酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到3-(2,4-dichlorophenoxy)-1-(4-methoxyphenyl)-4-(4-nitro-phenyl)azetidin-2-one
  参考文献：
  名称：

  Silphos as an efficient heterogeneous reagent for the synthesis of 2-azetidinones

  摘要：

  这份报告提供了一种高效简单的程序描述，用于在室温下通过亚磷硅和亚胺与羧酸的一锅法反应合成2-氮杂环丙酮。试剂便宜且稳定。产率从良好到优秀，反应条件温和。

  DOI：

  10.1515/hc-2014-0177

文献信息

• One-step Synthesis of β-lactams Using Cyanuric Fluoride
  作者：Maaroof Zarei

  DOI：10.3184/174751912x13545429290478

  日期：2013.1

  Cyanuric fluoride works as an efficient acid activator reagent for the direct [2+2] ketene–imine cycloaddition of substituted acetic acids and imines in a one-pot synthesis under mild conditions. The yields are good to excellent and the reaction conditions are mild, simple and efficient.

  氟化氰是一种高效的酸活化剂试剂，可在温和的条件下进行取代乙酸和亚胺的直接[2+2]酮-亚胺环化反应。反应条件温和、简单、高效，产率从良好到极佳。
• Utilization of DMF–PhCOCl Adduct as an Acid Activator in a New and Convenient Method for Preparation of β-Lactams
  作者：Maaroof Zarei

  DOI：10.1246/bcsj.20110323

  日期：2012.3.15

  An efficient one-pot synthesis of β-lactams by the reaction of imines with acetic acid derivatives in the presence of DMF and benzoyl chloride adduct, a cheap reagent, has been described. Optimizat...

  已经描述了通过亚胺与乙酸衍生物在 DMF 和苯甲酰氯加合物（一种廉价试剂）存在下的反应，高效地一锅法合成 β-内酰胺。优化...
• Silphos as an efficient heterogeneous reagent for the synthesis of 2-azetidinones
  作者：Maaroof Zarei、Aliasghar Jarrahpour

  DOI：10.1515/hc-2014-0177

  日期：2014.12.1

  This report provides a description of an efficient and simple procedure for the synthesis of 2-azetidinones via a one-pot reaction of imines and carboxylic acids in the presence of silicaphosphine at room temperature. The reagent is cheap and stable. The yields are good to excellent, and the reaction conditions are mild.

  这份报告提供了一种高效简单的程序描述，用于在室温下通过亚磷硅和亚胺与羧酸的一锅法反应合成2-氮杂环丙酮。试剂便宜且稳定。产率从良好到优秀，反应条件温和。
• Efficient one-pot synthesis of 2-azetidinones from acetic acid derivatives and imines using methoxymethylene-N,N-dimethyliminium salt
  作者：Aliasghar Jarrahpour、Maaroof Zarei

  DOI：10.1016/j.tet.2010.05.009

  日期：2010.7

  A cheap, versatile and convenient method for synthesis of beta-lactams using methoxymethylene-N,N-dimethyliminium salt as an acid activator in Staudinger reaction is reported. This method is used for the preparation of monocyclic, spirocyclic, N-alkyl and three-electron-withdrawing group beta-lactams. The products are obtained in good to excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.
• Thionation of β-lactams to β-thiolactams by silica-supported P₂S₅
  作者：Maaroof Zarei

  DOI：10.1080/17415993.2012.744407

  日期：2013.8.1

  In this paper, an improved method for the thionation of -lactams is described. Using a solid-supported P2S5 reagent and heating under reflux conditions, -thiolactams were obtained in good to excellent yields. Also the reaction time reduced significantly compared with that achieved under the more conventional method using P2S5 alone. Furthermore, inexpensive and easily available starting materials simple reaction conditions and a simple purification process are some other advantages of this method.[GRAPHICS].