3-methoxy-4-(4-nitrophenyl)-1-phenylazetidin-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-(4-nitrophenyl)-1-phenylazetidin-2-one
• 英文别名: (3S,4R)-3-methoxy-4-(4-nitrophenyl)-1-phenylazetidin-2-one
• 化学式: C₁₆H₁₄N₂O₄
• 分子量: 298.298
• InChiKey: MXPQXISKBLCFSW-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methoxy-4-(4-nitrophenyl)-1-phenylazetidin-2-one 在 silica-supported P₂S₅ 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以81%的产率得到3-methoxy-4-(4-nitrophenyl)-1-phenylazetidine-2-thione
  参考文献：
  名称：

  Thionation of β-lactams to β-thiolactams by silica-supported P₂S₅

  摘要：

  In this paper, an improved method for the thionation of -lactams is described. Using a solid-supported P2S5 reagent and heating under reflux conditions, -thiolactams were obtained in good to excellent yields. Also the reaction time reduced significantly compared with that achieved under the more conventional method using P2S5 alone. Furthermore, inexpensive and easily available starting materials simple reaction conditions and a simple purification process are some other advantages of this method.[GRAPHICS].

  DOI：

  10.1080/17415993.2012.744407
• 作为产物：
  描述：

  甲氧基乙酸 、 (4-硝基苄基亚基)苯胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到3-methoxy-4-(4-nitrophenyl)-1-phenylazetidin-2-one
  参考文献：
  名称：

  Silphos as an efficient heterogeneous reagent for the synthesis of 2-azetidinones

  摘要：

  这份报告提供了一种高效简单的程序描述，用于在室温下通过亚磷硅和亚胺与羧酸的一锅法反应合成2-氮杂环丙酮。试剂便宜且稳定。产率从良好到优秀，反应条件温和。

  DOI：

  10.1515/hc-2014-0177

文献信息

• Utilization of DMF–PhCOCl Adduct as an Acid Activator in a New and Convenient Method for Preparation of β-Lactams
  作者：Maaroof Zarei

  DOI：10.1246/bcsj.20110323

  日期：2012.3.15

  An efficient one-pot synthesis of β-lactams by the reaction of imines with acetic acid derivatives in the presence of DMF and benzoyl chloride adduct, a cheap reagent, has been described. Optimizat...

  已经描述了通过亚胺与乙酸衍生物在 DMF 和苯甲酰氯加合物（一种廉价试剂）存在下的反应，高效地一锅法合成 β-内酰胺。优化...
• A straightforward approach to 2-azetidinones from imines and carboxylic acids using dimethyl sulfoxide and acetic anhydride
  作者：Maaroof Zarei

  DOI：10.1016/j.tetlet.2014.07.089

  日期：2014.9

  The direct synthesis of 2-azetidinones from imines and carboxylic acids under mild conditions is developed. Dimethyl sulfoxide (DMSO) can be activated by acetic anhydride and the resulting active species is used for the in situ generation of ketenes from carboxylic acids. This method is cheap, simple, convenient, and efficient and the products are easily isolated.

  开发了在温和条件下由亚胺和羧酸直接合成2-氮杂环丁酮的方法。二甲基亚砜（DMSO）可以被乙酸酐活化，所得的活性物质可用于从羧酸原位生成乙烯酮。该方法便宜，简单，方便，高效，并且产品易于分离。
• Silphos as an efficient heterogeneous reagent for the synthesis of 2-azetidinones
  作者：Maaroof Zarei、Aliasghar Jarrahpour

  DOI：10.1515/hc-2014-0177

  日期：2014.12.1

  This report provides a description of an efficient and simple procedure for the synthesis of 2-azetidinones via a one-pot reaction of imines and carboxylic acids in the presence of silicaphosphine at room temperature. The reagent is cheap and stable. The yields are good to excellent, and the reaction conditions are mild.

  这份报告提供了一种高效简单的程序描述，用于在室温下通过亚磷硅和亚胺与羧酸的一锅法反应合成2-氮杂环丙酮。试剂便宜且稳定。产率从良好到优秀，反应条件温和。
• A convenient synthesis of 2-azetidinones via 2-fluoro-1-methylpyridinium p-toluenesulfonate
  作者：Maaroof Zarei

  DOI：10.1007/s00706-012-0918-y

  日期：2013.7

  The application and versatility of 2-fluoro-1-methylpyridinium p-toluenesulfonate as acid activator in the synthesis of several beta-lactams under mild reaction conditions by use of ketene-imine cycloaddition reactions has been investigated. The effects of solvents, molar ratio of reagents, and temperature were considered. The method was also used for preparation of beta-lactams substituted in position 3 by electron-withdrawing groups. The products are obtained in good to excellent yields..
• β-Lactam Preparation via Staudinger Reaction with Activated Dimethylsulfoxide
  作者：Maaroof Zarei

  DOI：10.1002/jhet.2685

  日期：2017.3

  efficient synthesis of β‐lactams has been expediently accomplished. These β‐lactams were synthesized by the Staudinger reaction of several substituted imines with various carboxylic acids using activated DMSO at ambient temperature. The imines and substituted acetic acids contain alkyl, aryl, hetero aryl, polycyclic, and 3‐electron‐withdrawing group underwent [2 + 2] ketene‐imine cycloaddition reaction

  方便地完成了β-内酰胺的有效合成。这些β-内酰胺是在室温下使用活化的DMSO通过几种取代的亚胺与各种羧酸的Staudinger反应合成的。亚胺和取代的乙酸包含烷基，芳基，杂芳基，多环和3-吸电子基团，平稳地进行[2 + 2]乙烯酮-亚胺环加成反应，以良好至极好的收率获得所需的β-内酰胺。该方法便宜，简单，方便，高效，产品易于分离。