3-(naphthalen-2-yloxy)-4-(4-nitrophenyl)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-(naphthalen-2-yloxy)-4-(4-nitrophenyl)azetidin-2-one
• 英文别名: (3S,4R)-3-naphthalen-2-yloxy-4-(4-nitrophenyl)azetidin-2-one
• 化学式: C₁₉H₁₄N₂O₄
• 分子量: 334.331
• InChiKey: OOWADFQBQVVQFC-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-乙氧基苯基-N-(4-硝基苯亚甲基)胺 在 ammonium cerium(IV) nitrate 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.5h， 生成 3-(naphthalen-2-yloxy)-4-(4-nitrophenyl)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

• From Solution-Phase to ‘On-Column’ N-Dearylation of β-Lactams by Silica-Supported Ceric Ammonium Nitrate (CAN-SiO₂)
  作者：Aliasghar Jarrahpour、Maaroof Zarei

  DOI：10.1055/s-2008-1032051

  日期：2008.2

  It has been shown that N-(4-methoxy or 4-ethoxyphenyl) groups can be oxidatively removed by silica gel supported ceric ammonium nitrate (CAN-SiO2) under mild conditions in solution and on column. The yields in these two methods were good to excellent and purification of products is simpler than the general method by CAN. Especially the ‘on-column’ reaction is mild, easy, efficient, and cheap. The lower mobility of CAN-SiO2 makes it safer to handle.

  研究表明，N-(4-甲氧基或4-乙氧基苯基)基团可以在温和条件下通过硅胶支持的铈铵硝酸盐（CAN-SiO2）进行氧化去除。在这两种方法中，产率均为良好至优秀，产品的纯化也比一般的CAN方法简单。特别是“柱上”反应温和、简单、高效且成本低廉。CAN-SiO2的较低流动性使其更安全易于操作。
• Ceric Ammonium Nitrate on Silica Gel for Solid–Solid Phase<i>N</i>-Dearylation of β -Lactams
  作者：Aliasghar Jarrahpour、Maaroof Zarei

  DOI：10.1080/10426500802336630

  日期：2009.7.13

  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.
• 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.
• Synthesis of N-unsubstituted β-lactams from N-alkoxyphenyl-β-lactams with cobalt(III) fluoride
  作者：Maaroof Zarei、Aliasghar Jarrahpour

  DOI：10.1016/j.tetlet.2010.08.101

  日期：2010.11

  Mild and efficient oxidative N-dearylation of N-alkoxyphenyl-beta-lactams with cobalt(III) fluoride proceeded in good to excellent yields to afford the corresponding N-unsubstituted beta-lactams. Optimization of the solvent, molar ratio of reagents, time, and temperature are described. (C) 2010 Elsevier Ltd. All rights reserved.