3-chloro-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one | 22085-96-7

• 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-chloro-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one
• 英文别名: 3-chloro-1-(4-methoxyphenyl)-4-phenylazetidin-2-one；(3S,4R)-3-chloro-1-(4-methoxyphenyl)-4-phenylazetidin-2-one
• CAS: 22085-96-7；127680-27-7
• 化学式: C₁₆H₁₄ClNO₂
• 分子量: 287.746
• InChiKey: SSFYHSIUVSXXSV-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 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：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chloro-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 在 水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以84%的产率得到cis 3-chloro-4-phenylazetidin-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
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 以28 %的产率得到3-chloro-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one
  参考文献：
  名称：

  Synthetic investigations in epimerization reactions of β-lactams

  摘要：

  DOI：

  10.56042/ijc.v61i7.64639

文献信息

• 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。
• Electrochemical studies on β-lactams. Part 4. Electroacetylation of β-lactams.
  作者：Maria Antonietta Casadei、Achille Inesi、Franco Micheletti Moracci、Donatella Occhialini

  DOI：10.1016/s0040-4020(01)89156-0

  日期：1989.1

  Electroreduction of 3-bromo- and 3, 3-dichloro-β-lactams 1 carried out at the potential of the first voltammetric peak and in the presence of acetic anhydride gives 3-acetyl-β-lactams 2. The electrosynthesis is highly stereoselective, as only the acetyl derivative with trans configuration is formed.

  在第一个伏安峰的电势下，在乙酸酐的存在下，进行3-溴-和3,3-二氯-β-内酰胺2的电还原，得到3-乙酰基-β-内酰胺2。电合成是高度立体选择性的，因为仅形成具有反式构型的乙酰基衍生物。
• A Mild and Efficient Route to 2-Azetidinones Using the Cyanuric Chloride-DMF Complex
  作者：Aliasghar Jarrahpour、Maaroof Zarei

  DOI：10.1055/s-0030-1289517

  日期：2011.10

  Efficient conversion of Schiff bases and carboxylic acids to β-lactams can be carried out at room temperature in CH2Cl2, using a cyanuric chloride-N,N-dimethyl formamide complex. The complex is easily prepared by reaction of cyanuric chloride and DMF, an inexpensive reagent, at room temperature. Optimization of conditions and comparison of yield with cyanuric chloride were performed.

  在室温下，利用氰尿酰氯-N,N-二甲基甲酰胺复合物，可以在CH2Cl2中高效地将席夫碱和羧酸转化为β-内酰胺。通过在室温下将氰尿酰氯与低成本试剂DMF反应，可以轻松制备该复合物。优化了条件并比较了产率与氰尿酰氯的结果。
• 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。
• Synthesis of β‐Lactams: α‐Chloro and α‐Cyano β‐Lactams by Condensation of Imines with Titanium Ester Enolates Derived from Chloro and Cyano Ethyl Acetates
  作者：Seema Kanwar、S. D. Sharma

  DOI：10.1080/00397910500181947

  日期：2005.8.1

  Abstract α‐Cyano and α‐chloro β‐lactams are obtained in a one‐step reaction at a temperature of less than −78°C by condensation of imines with ester enolates derived from ethyl α‐cyano and α‐chloro acetates.

  摘要 α-氰基和α-氯β-内酰胺是在低于-78°C 的温度下通过一步反应通过亚胺与α-氰基乙酯和α-氯乙酸酯衍生的酯烯醇缩合获得的。