3-chloro-1,4-bis-(4-methoxy-phenyl)-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: 3-chloro-1,4-bis-(4-methoxy-phenyl)-azetidin-2-one
• 英文别名: cis-3-chloro-1-(4-methoxyphenyl)-4-(4-methoxyphenyl)azetidin-2-one；cis-1-(4'-methoxyphenyl)-3-chloro-4-(4'-methoxyphenyl)azetidin-2-one；(3R,4S)-3-chloro-1,4-bis(4-methoxyphenyl)azetidin-2-one
• 化学式: C₁₇H₁₆ClNO₃
• 分子量: 317.772
• InChiKey: MAKSLGJOEWEGAR-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  3-chloro-1,4-bis-(4-methoxy-phenyl)-azetidin-2-one 在 水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以82%的产率得到cis 3-chloro-4-(4-methoxyphenyl)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
• 作为产物：
  描述：

  trans-3-chloro-1-(4-methoxyphenyl)-4-(4-methoxyphenyl)azetidin-2-one 在 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 以35 %的产率得到3-chloro-1,4-bis-(4-methoxy-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

• Heterogeneous Catalysis with Basic Compounds to Achieve the Synthesis and C–N Cleavage of Azetidin-2-ones under Microwave Irradiation
  作者：Adriana Galván、Fabiola N. de la Cruz、Francisco Cruz、Merced Martínez、Clarisa Villegas Gomez、Yolanda Alcaraz、José Manuel Domínguez、Francisco Delgado、Miguel A. Vázquez

  DOI：10.1055/s-0037-1611851

  日期：2019.10

  scanning electron microscopy (SEM), and high-resolution transmission electron microscopy (HR-TEM). The synthesis of azetidin-2-ones with a completely heterogeneous catalysis is reported. The use of basic compounds as solid catalysts allowed for the synthesis of azetidin-2-ones under microwave irradiation without organic additives such as triethylamine. An excellent catalyst for this transformation was

  抽象的 据报道，氮杂环丁烷-2-酮具有完全多相催化的合成。使用碱性化合物作为固体催化剂可以在没有有机添加剂如三乙胺的微波辐射下合成氮杂环丁烷-2-酮。用于该转化的极好的催化剂是Mg-Al氢氧化物（MAH）。本方法提供了无危险的反应条件，短的反应时间，高产率和催化剂可重复使用性的优点。在亚胺和酰氯上测试了不同的取代基，以探索反应的范围。在氮杂环丁烷-2-酮中检测到非常规的N–C4键断裂。MAH的特征在于N 2 吸附-解吸，X射线衍射（XRD），扫描电子显微镜（SEM）和高分辨率透射电子显微镜（HR-TEM）。 据报道，氮杂环丁烷-2-酮具有完全多相催化的合成。使用碱性化合物作为固体催化剂可以在没有有机添加剂如三乙胺的微波辐射下合成氮杂环丁烷-2-酮。用于该转化的极好的催化剂是Mg-Al氢氧化物（MAH）。本方法提供了无危险的反应条件，短的反应时间，高产率和催化剂可重复使用性的优点。在亚胺和酰
• Carbocation catalyzed carboxylic acid activation in Staudinger reaction for stereoselective synthesis of β-lactams
  作者：Ankita Rai、Puneet K. Singh、Prashant Shukla、Vijai K. Rai

  DOI：10.1016/j.tetlet.2016.10.012

  日期：2016.11

  stereoselective β-lactams has been disclosed via cyclopropenium-ion-catalyzed reaction of substituted acetic acids with aldimines under mild conditions. Products are formed in high yields (86–95%) and good diastereoselectivity within 3–4 h. The new reaction is focused on the exploration of the scope of cyclopropenium-ion catalysis and introduction of a catalytic version of one-step Staudinger reaction for β-lactam

  已经公开了通过在温和的条件下环乙酸离子催化的取代乙酸与醛亚胺的合成立体选择性β-内酰胺的新策略。产物在3-4小时内以高收率（86–95％）和良好的非对映选择性形成。该新反应的重点是探索环丙烯离子催化的范围，并引入了用于一步一步Staudinger反应的催化型β-内酰胺合成方法。该反应对于一系列取代的乙酸和醛亚胺是有效的。
• 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。
• 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。
• Efficient one-pot synthesis of 2-azetidinones from acetic acid derivatives and imines using methoxymethylene-N,N-dimethyliminium salt
  作者：Aliasghar Jarrahpour、Maaroof Zarei

  DOI：10.1016/j.tet.2010.05.009

  日期：2010.7

  A cheap, versatile and convenient method for synthesis of beta-lactams using methoxymethylene-N,N-dimethyliminium salt as an acid activator in Staudinger reaction is reported. This method is used for the preparation of monocyclic, spirocyclic, N-alkyl and three-electron-withdrawing group beta-lactams. The products are obtained in good to excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.