4-(4-chlorophenyl)-3-(naphthalen-2-yloxy)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-(naphthalen-2-yloxy)azetidin-2-one
• 英文别名: (3S,4R)-4-(4-chlorophenyl)-3-naphthalen-2-yloxyazetidin-2-one
• 化学式: C₁₉H₁₄ClNO₂
• 分子量: 323.779
• InChiKey: SPJOAYYAOHRBBP-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 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：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  cis-1-(4-methoxybenzyl)-4-(4-chlorophenyl)-3-(naphthalen-2-yloxy)azetidin-2-one 在 水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以88%的产率得到4-(4-chlorophenyl)-3-(naphthalen-2-yloxy)azetidin-2-one
  参考文献：
  名称：

  On-column N-dearylation of 2-azetidinones by silica-supported ceric ammonium nitrate

  摘要：

  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.

  DOI：

  10.1016/j.tet.2012.04.088

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。
• 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.
• 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.