(3S,4S)-4-(4-nitrophenyl)-1,3-diphenyl-2-azetidinone | 1186503-08-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3S,4S)-4-(4-nitrophenyl)-1,3-diphenyl-2-azetidinone
• 英文别名: (3S,4S)-4-(4-nitrophenyl)-1,3-diphenylazetidin-2-one
• CAS: 1186503-08-1
• 化学式: C₂₁H₁₆N₂O₃
• 分子量: 344.37
• InChiKey: BNEOTIHENQPSTP-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-二氮杂-1-苯乙酮 、 (4-硝基苄基亚基)苯胺 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 12.0h， 以37%的产率得到2-Azetidinone, 4-(4-nitrophenyl)-1,3-diphenyl-, trans-
  参考文献：
  名称：

  由热沃尔夫重排产生的二茂铁烯酮一锅法合成反式β-内酰胺

  摘要：

  摘要 通过相应重氮酮的热沃尔夫重排产生的二茂铁基烯酮与各种亚胺之间的施陶丁格反应合成了一系列含有二茂铁部分的β-内酰胺。立体化学结果已被研究，反式产物作为主要产物被分离出来，这与 Bonini 和同事报告的结果相反。(±)-trans-1,4-diphenyl-3-ferrocenylazetidin-2-one (3c) 的绝对构型通过 X 射线分析确定。从反应机理的角度讨论立体选择性。图形概要

  DOI：

  10.1080/00397911.2017.1378358

文献信息

• Enantioselective synthesis of β-lactams via the IndaBox–Cu(II)-catalyzed Kinugasa reaction
  作者：Takao Saito、Tomohiro Kikuchi、Hiroaki Tanabe、Junichi Yahiro、Takashi Otani

  DOI：10.1016/j.tetlet.2009.06.050

  日期：2009.9

  The enantioselective Kinugasa reaction of nitrones with terminal alkynes in the presence of 20 mol % of IndaBox–Cu(OTf)2 and di-sec-butylamine (1.5 equiv) produced β-lactams with the highest level of enantiomeric excesses among the catalytic enantioselective Kinugasa reactions reported so far.

  在20 mol％IndaBox–Cu（OTf）2和二仲丁胺（1.5当量）的存在下，硝酮与末端炔烃的对映选择性Kinugasa反应生成的β-内酰胺在催化对映选择性Kinugasa中具有最高的对映体过量水平迄今已报道了反应。
• Preparation and characterization of cyclohexandiamine/Fe ₃ O ₄ /ZnO core/shell nanomagnetic composite as a novel reusable catalyst and its application for the diastereoselective synthesis of β‐lactams via the asymmetric Kinugasa reaction
  作者：Javad Safaei‐Ghomi、Safura Zahedi

  DOI：10.1002/aoc.3763

  日期：2017.11

  A novel magnetic composite catalyst has been prepared by immobilizing a chiral diamine on core/shell Fe3O4/ZnO. This new catalyst was characterized using X‐ray diffraction, energy‐dispersive X‐ray analysis, Fourier transform infrared spectroscopy, scanning electron microscopy, thermogravimetric analysis and vibrating sample magnetometry. The performance of the catalyst was investigated in the asymmetric

  通过将手性二胺固定在核/壳Fe 3 O 4 / ZnO上制备了新型磁性复合催化剂。通过X射线衍射，能量色散X射线分析，傅立叶变换红外光谱，扫描电子显微镜，热重分析和振动样品磁强分析对这种新型催化剂进行了表征。在不对称的Kinugasa反应中研究了催化剂的性能，证实了该催化剂在温和条件下可有效合成β-内酰胺衍生物。
• Tris(oxazoline)/copper-catalyzed coupling of alkynes with nitrones: a highly enantioselective access to β-lactams
  作者：Jiang-Hua Chen、Sai-Hu Liao、Xiu-Li Sun、Qi Shen、Yong Tang

  DOI：10.1016/j.tet.2012.04.049

  日期：2012.6

  Chiral tris(oxazoline)/Cu(I) complexes are demonstrated as a type of efficient catalysts for the asymmetric Kinugasa reaction of terminal alkynes with C-arylnitrones, providing a highly enantio- and diastereoselective access to optically active beta-lactams. (C) 2012 Elsevier Ltd. All rights reserved.
• Studies of multicomponent Kinugasa reactions in aqueous media
  作者：Craig S. McKay、David C. Kennedy、John Paul Pezacki

  DOI：10.1016/j.tetlet.2009.02.035

  日期：2009.4

  Micelle-promoted, copper-catalyzed multicomponent Kinugasa reactions were studied in aqueous media. Reactions were performed in a 'single pot' for a series of in situ generated C,N-diphenylnitrones with Cu(I) phenylacetylide providing beta-lactams in yields of 45-85%. Substituents affect the reaction by either accelerating cycloaddition or minimizing side reactions. (C) 2009 Elsevier Ltd. All rights reserved.
• One-pot synthesis of <i>trans</i>-<font>β</font>-lactams from ferrocenylketene generated by thermal Wolff rearrangement
  作者：Mingshun Liu、Jian’an Wang、Xiaoxi Yuan、Rong Jiang、Nanyan Fu

  DOI：10.1080/00397911.2017.1378358

  日期：2017.12.17

  ABSTRACT A series of β-lactams containing the ferrocene moiety were synthesized through the Staudinger reaction between ferrocenylketene generated by the thermal Wolff rearrangement of the corresponding diazo ketone and various imines. The stereochemical outcome has been investigated and the trans-products were isolated as the main products, opposite to the reported results by Bonini and coworkers

  摘要 通过相应重氮酮的热沃尔夫重排产生的二茂铁基烯酮与各种亚胺之间的施陶丁格反应合成了一系列含有二茂铁部分的β-内酰胺。立体化学结果已被研究，反式产物作为主要产物被分离出来，这与 Bonini 和同事报告的结果相反。(±)-trans-1,4-diphenyl-3-ferrocenylazetidin-2-one (3c) 的绝对构型通过 X 射线分析确定。从反应机理的角度讨论立体选择性。图形概要