4-(4-chlorophenyl)-3-phenoxyazetidin-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-phenoxyazetidin-2-one
• 英文别名: (3S,4R)-4-(4-chlorophenyl)-3-phenoxyazetidin-2-one
• 化学式: C₁₅H₁₂ClNO₂
• 分子量: 273.719
• InChiKey: VLCHPYLTNXZESE-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(4-氯苯基)-N-(4-乙氧基苯基)甲亚胺 在 ammonium cerium(IV) nitrate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.5h， 生成 4-(4-chlorophenyl)-3-phenoxyazetidin-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

• Cerium(IV) Tetrabutylammonium Nitrate (CTAN): A Mild and Efficient N-dearylation Agent for Synthesis of N-unsubstituted 2-azetidinones
  作者：Maaroof Zarei

  DOI：10.3184/174751917x14902201357392

  日期：2017.4

  A simple and efficient protocol for the conversion of N-p-methoxyphenyl, N-p-ethoxyphenyl, N-p-methoxynaphthyl, N-3,4-dimethoxybenzyl and N-p-methoxybenzyl-2-azetidinones to N-unsubstituted 2-azetidinones using cerium(IV) tetrabutylammonium nitrate (CTAN) in dichloromethane is described. The method is compatible with a number of functional groups, and N-unsubstituted 2-azetidinones can be prepared

  使用四丁基硝酸铈 (IV) 将 Np-甲氧基苯基、Np-乙氧基苯基、Np-甲氧基萘基、N-3,4-二甲氧基苄基和 Np-甲氧基苄基-2-氮杂环丁酮转化为 N-未取代的 2-氮杂环丁烷酮的简单有效方案(CTAN) 在二氯甲烷中进行了描述。该方法与许多官能团兼容，并且可以在室温下温和条件下制备 N-未取代的 2-氮杂环丁酮。反应迅速，以良好的收率获得纯产物。
• 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.
• Enantioselective hydrolysis of 3,4-disubstituted β-lactams. An efficient enzymatic method for the preparation of a key Taxol side-chain intermediate
  作者：Zsolt Galla、Ferenc Beke、Enikő Forró、Ferenc Fülöp

  DOI：10.1016/j.molcatb.2015.11.011

  日期：2016.1

  3,4-Disubstituted beta-lactams 3-benzyloxy-4-(4-chlorophenyl)azetidin-2-one [(3S*,4R*)-(+/-)-1], 3-benzyloxy-4-phenylazetidin-2-one [(3S*,4R*)-(+/-)-2] and 4-(4-chlorophenyl)-3-phenoxyazetidin-2-one [(3S*,4R*)-(+/-)-3] were resolved through immobilized CAL-B-catalysed ring-cleavage reactions. Excellent enantioselectivities (E>200) were obtained for (3S*,4R*)-(+/-)-1 and (3S*,4R*)-(+/-)-2 when the reactions were performed with added H2O as nucleophile in tert-butyl methyl ether at 70 degrees C, whereas only moderate E (12) was achieved for (3S*,4R*)-(+/-)-3 under the same conditions but in diisopropyl ether. The resulting ring-opened beta-amino acids [(2R,3S)-4 (ee>98%), (2R,3S)-5 (ee > 98%) and (2R,3S)-6 (ee = 50%)] and the unreacted beta-lactams [(3S,4R)-1-3] (ee > 98%) could be easily separated. (C) 2015 Elsevier B.V. All rights reserved.
• Synthesis of Novel N-(4-Ethoxyphenyl) Azetidin-2-ones and Their Oxidative N-Deprotection by Ceric Ammonium Nitrate
  作者：Aliasghar Jarrahpour、Maaroof Zarei

  DOI：10.3390/12102364

  日期：——

  It is shown that the N-(p-ethoxyphenyl) group on beta-lactams can be oxidatively removed by ceric ammonium nitrate in good yield. Fourteen new N-(p-ethoxyphenyl)-2-azetidinones 8a-n were synthesized through standard [2+2] ketene-imine cycloadditions (Staudinger reaction). Treatment of these compounds with ceric ammonium nitrate yielded the N-dearylated 2-azetidinones 9a-n in good to excellent yields

  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。