4-(4-chlorophenyl)-1-(4-methoxyphenyl)-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)-1-(4-methoxyphenyl)-3-phenoxyazetidin-2-one
• 英文别名: (3S,4R)-4-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-phenoxyazetidin-2-one
• 化学式: C₂₂H₁₈ClNO₃
• 分子量: 379.843
• InChiKey: MPAJUAQMCWLKOV-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-phenoxyazetidin-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4-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-phenoxyazetidine-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：

  1-(4-氯苯基)-N-(4-甲氧基苯基)甲亚胺 、 苯氧乙酸 在 乙酸酐 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到4-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-phenoxyazetidin-2-one
  参考文献：
  名称：

  一种简单的方法，使用二甲基亚砜和乙酸酐从亚胺和羧酸中合成2-氮杂环丁酮

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2014.07.089

文献信息

• 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。
• The Vilsmeier reagent: a useful and versatile reagent for the synthesis of 2-azetidinones
  作者：Aliasghar Jarrahpour、Maaroof Zarei

  DOI：10.1016/j.tet.2009.02.005

  日期：2009.4

  and oxalyl chloride or thionyl chloride, works as a versatile acid activator reagent for the direct [2+2] ketene–imine cycloaddition of substituted acetic acid and imines in one-pot synthesis under mild conditions. Monocyclic, spirocyclic and 3-electron-withdrawing group β-lactams were synthesized by this method and optimization of conditions were performed.

  （氯亚甲基）二甲基氯化铵（Vilsmeier试剂），可以轻松地由N，N-二甲基甲酰胺和草酰氯或亚硫酰氯制备，可作为通用的酸活化剂，用于直接[2 + 2]烯酮-亚胺环加成取代的乙酸和亚胺在温和条件下一锅合成。用该方法合成了单环，螺环和3个吸电子基β-内酰胺，并进行了条件优化。
• 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。
• 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。