1-(4-ethoxyphenyl)-4-(4-nitrophenyl)-3-phenoxy-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-(4-ethoxyphenyl)-4-(4-nitrophenyl)-3-phenoxy-azetidin-2-one
• 英文别名: 1-(4-ethoxyphenyl)-4-(4-nitrophenyl)-3-phenoxyazetidin-2-one；(3S,4R)-1-(4-ethoxyphenyl)-4-(4-nitrophenyl)-3-phenoxyazetidin-2-one
• 化学式: C₂₃H₂₀N₂O₅
• 分子量: 404.422
• InChiKey: CAAFINCEBTYBGZ-YADHBBJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  1-(4-ethoxyphenyl)-4-(4-nitrophenyl)-3-phenoxy-azetidin-2-one 在 silica-supported P₂S₅ 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以77%的产率得到1-(4-ethoxyphenyl)-4-(4-nitrophenyl)-3-phenoxyazetidine-2-thione
  参考文献：
  名称：

  Thionation of β-lactams to β-thiolactams by silica-supported P₂S₅

  摘要：

  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].

  DOI：

  10.1080/17415993.2012.744407
• 作为产物：
  描述：

  对硝基苯甲醛 在 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 1-(4-ethoxyphenyl)-4-(4-nitrophenyl)-3-phenoxy-azetidin-2-one
  参考文献：
  名称：

  新型 N-(4-ethoxyphenyl) azetidin-2-ones 的合成及其硝酸铈铵的氧化 N-脱保护。

  摘要：

  结果表明，硝酸铈铵可以以良好的收率氧化去除β-内酰胺上的N-(对乙氧基苯基)基团。通过标准的 [2+2] 烯酮-亚胺环加成反应（施陶丁格反应）合成了 14 种新的 N-（对乙氧基苯基）-2-氮杂环丁烷酮 8a-n。用硝酸铈铵处理这些化合物产生了 N-脱芳基化 2-氮杂环丁酮 9a-n，产率良好至极好。研究了溶剂、CAN摩尔当量和不同温度的影响，并建立了最佳条件。

  DOI：

  10.3390/12102364

文献信息

• The Vilsmeier reagent: a useful and versatile reagent for the synthesis of 2-azetidinones
  作者：Aliasghar Jarrahpour、Maaroof Zarei

  DOI：10.1016/j.tet.2009.02.005

  日期：2009.4

  and oxalyl chloride or thionyl chloride, works as a versatile acid activator reagent for the direct [2+2] ketene–imine cycloaddition of substituted acetic acid and imines in one-pot synthesis under mild conditions. Monocyclic, spirocyclic and 3-electron-withdrawing group β-lactams were synthesized by this method and optimization of conditions were performed.

  （氯亚甲基）二甲基氯化铵（Vilsmeier试剂），可以轻松地由N，N-二甲基甲酰胺和草酰氯或亚硫酰氯制备，可作为通用的酸活化剂，用于直接[2 + 2]烯酮-亚胺环加成取代的乙酸和亚胺在温和条件下一锅合成。用该方法合成了单环，螺环和3个吸电子基β-内酰胺，并进行了条件优化。
• 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...
• The Vilsmeier reagent as an efficient acid activator for the synthesis of β-lactams
  作者：Aliasghar Jarrahpour、Maaroof Zarei

  DOI：10.1016/j.tetlet.2007.10.012

  日期：2007.12

  The Vilsmeier reagent (chloromethylenedimethylammonium chloride) has been used as an efficient and cheap acid activator for the one-step Staudinger reaction of substituted acetic acids and imines under mild conditions. This reaction is clean and the by-products are DMF and triethylamine hydrochloride which were removed by simple aqueous work-up. (c) 2007 Published by Elsevier Ltd.
• Solid‐Solid Phase and Solvent‐Free Oxidative Removal of<i>N</i>‐(4‐Alkoxyphenyl) Groups of Monocyclic β‐Lactams with Ceric Ammonium Nitrate as a Cheap, Simple, and Efficient Method
  作者：Aliasghar Jarrahpour、M. Zarei

  DOI：10.1080/00397910801981326

  日期：2008.5

  Five N-(4-methoxyphenyl)- and five N-(4-ethoxyphenyl)-beta-lactams were prepared by ketene-imine [2+2] cycloaddition (Staudinger reaction). Then these 2-azetidinones were N-dearylated by grinding together with ceric ammonium nitrate without hazardous solvents in good to excellent yields. The solid-solid phase N-dearylation is easier, simpler, and more efficient than the general method in solution. The pure N-unsubstituted beta-lactams obtained by a nontedious workup and without further purification.
• Argentic oxide mediated N-dearylation of β-lactams
  作者：Maaroof Zarei、Aliasghar Jarrahpour

  DOI：10.1016/j.tetlet.2011.01.022

  日期：2011.3

  A method is described for the N-dearylation of N-(4-methoxy- or 4-ethoxyphenyl)-2-azetidinones with argentic oxide. The yields are good-to-excellent and the reaction is simple, efficient, and fast. (C) 2011 Elsevier Ltd. All rights reserved.