3-methoxy-4-p-tolylazetidin-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-methoxy-4-p-tolylazetidin-2-one
• 英文别名: (3S,4R)-3-methoxy-4-(4-methylphenyl)azetidin-2-one
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: HLVSAGUUWBLDNH-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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-methoxyphenyl)-3-methoxy-4-p-tolylazetidin-2-one 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以79%的产率得到3-methoxy-4-p-tolylazetidin-2-one
  参考文献：
  名称：

  Synthesis of N-unsubstituted β-lactams from N-alkoxyphenyl-β-lactams with cobalt(III) fluoride

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2010.08.101

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。
• 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.