4-(4-chlorophenyl)-3-(2,4-dichlorophenoxy)-1-(4-ethoxyphenyl)-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: 4-(4-chlorophenyl)-3-(2,4-dichlorophenoxy)-1-(4-ethoxyphenyl)-azetidin-2-one
• 英文别名: 4-(4-chlorophenyl)-3-(2,4-dichlorophenoxy)-1-(4-ethoxyphenyl)azetidin-2-one；(3S,4R)-4-(4-chlorophenyl)-3-(2,4-dichlorophenoxy)-1-(4-ethoxyphenyl)azetidin-2-one
• 化学式: C₂₃H₁₈Cl₃NO₃
• 分子量: 462.76
• InChiKey: GLOKCTWLFSSTRG-YADHBBJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 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：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-chlorophenyl)-3-(2,4-dichlorophenoxy)-1-(4-ethoxyphenyl)-azetidin-2-one 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.75h， 以82%的产率得到4-(4-chlorophenyl)-3-(2,4-dichlorophenoxy)azetidin-2-one
  参考文献：
  名称：

  Ceric Ammonium Nitrate on Silica Gel for Solid–Solid PhaseN-Dearylation of β -Lactams

  摘要：

  Silica gel-supported ceric ammonium nitrate (CAN-SiO(2)) has been found to be an effective reagent for the solid-solid phase and solvent-free N-dearylation of beta-lactams. The results have been compared with CAN alone in solution and solid-solid phase.

  DOI：

  10.1080/10426500802336630
• 作为产物：
  描述：

  2,4-二氯苯氧乙酸 、 1-(4-氯苯基)-N-(4-乙氧基苯基)甲亚胺 在 (氯亚甲基)二甲基氯化铵 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到4-(4-chlorophenyl)-3-(2,4-dichlorophenoxy)-1-(4-ethoxyphenyl)-azetidin-2-one
  参考文献：
  名称：

  Vilsmeier试剂：一种用于合成2-氮杂环丁烷酮的有用且用途广泛的试剂

  摘要：

  （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。

  DOI：

  10.1016/j.tet.2009.02.005

文献信息

• 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.
• 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.
• 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.
• On-column N-dearylation of 2-azetidinones by silica-supported ceric ammonium nitrate
  作者：Maaroof Zarei、Aliasghar Jarrahpour、Edris Ebrahimi、Malihe Aye、Seid Ali Torabi Badrabady

  DOI：10.1016/j.tet.2012.04.088

  日期：2012.7

  A modified traditional preparative chromatographic column can be used to achieve quantitative N-dearylation of N-(alkoxyphenyl), N-(alkoxynaphthyl), and N-(alkoxybenzyl)-2-azetidinones under mild conditions. Starting materials are charged on top of the column and the pure N-unsubstituted 2-azetidinones leave the column minutes later without need for other purifications. The yields are good-to-excellent and the reaction condition is mild, easy, efficient, and cheap. (c) 2012 Elsevier Ltd. All rights reserved.