2-吖丁啶酮,4-(4-硝基苯基)-3-苯氧基-1-(苯基甲基)-,顺- | 105602-02-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 中文名称: 2-吖丁啶酮,4-(4-硝基苯基)-3-苯氧基-1-(苯基甲基)-,顺-
• 英文名称: 1-benzyl-4-(4-nitrophenyl)-3-phenoxyazetidin-2-one
• 英文别名: (3S,4R)-1-benzyl-4-(4-nitrophenyl)-3-phenoxyazetidin-2-one
• CAS: 105602-02-6
• 化学式: C₂₂H₁₈N₂O₄
• 分子量: 374.396
• InChiKey: IFOQWMAXMUIRML-RTWAWAEBSA-N

物化性质

• 熔点：
  130-132 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  605.5±55.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 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：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-吖丁啶酮,4-(4-硝基苯基)-3-苯氧基-1-(苯基甲基)-,顺- 在 silica-supported P₂S₅ 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以81%的产率得到1-benzyl-4-(4-nitrophenyl)-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：

  苯氧乙酸 、 N-苄基-1-(4-硝基苯基)甲亚胺 在 Benzoyloxymethylene-dimethyl-ammonium; chloride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到2-吖丁啶酮,4-(4-硝基苯基)-3-苯氧基-1-(苯基甲基)-,顺-
  参考文献：
  名称：

  利用 DMF-PhCOCl 加合物作为酸活化剂制备 β-内酰胺的新方法

  摘要：

  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...

  DOI：

  10.1246/bcsj.20110323

文献信息

• One-step Synthesis of β-lactams Using Cyanuric Fluoride
  作者：Maaroof Zarei

  DOI：10.3184/174751912x13545429290478

  日期：2013.1

  Cyanuric fluoride works as an efficient acid activator reagent for the direct [2+2] ketene–imine cycloaddition of substituted acetic acids and imines in a one-pot synthesis under mild conditions. The yields are good to excellent and the reaction conditions are mild, simple and efficient.

  氟化氰是一种高效的酸活化剂试剂，可在温和的条件下进行取代乙酸和亚胺的直接[2+2]酮-亚胺环化反应。反应条件温和、简单、高效，产率从良好到极佳。
• New fragmentation and rearrangement reactions of the azetidine ring promoted by AlEt2Cl
  作者：Benito Alcaide、Nati R Salgado、Miguel A Sierra

  DOI：10.1016/s0040-4039(97)10577-9

  日期：1998.1

  Azetidines 6 prepared by AlH2Cl reduction of easily available β-lactams 5 react with AlEt2Cl in CH2Cl2 solution at room temperature to yield, through new fragmentation or rearrangement reactions of the azetidine ring, either, olefins 7 or bicyclic fused pyrrolidines 8, depending on the nature of the group bonded to C2 of the four membered ring.

  通过AlH 2 Cl还原易得的β-内酰胺5制备的氮杂环丁烷6在室温下与AlEt 2 Cl在CH 2 Cl 2溶液中反应，通过氮杂环丁烷环的新断裂或重排反应生成烯烃7或双环稠合吡咯烷8，取决于与四元环的C 2键合的基团的性质。
• 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.
• Sharma, S. D.; Kaur, S.; Mehra, Usha, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 141 - 144
  作者：Sharma, S. D.、Kaur, S.、Mehra, Usha

  DOI：——

  日期：——
• Novel Diethylaluminum Chloride Promoted Reactions of the Azetidine Ring:  Efficient and Stereocontrolled Entry to Functionalized Olefins, Pyrrolidines, and Pyrroles
  作者：Benito Alcaide、Pedro Almendros、Cristina Aragoncillo、Nati R. Salgado

  DOI：10.1021/jo991203c

  日期：1999.12.1

  The first examples of Lewis acid promoted fragmentation or rearrangement of the azetidine ring are reported. Azetidine precursors, cis-beta-lactams, were easily available as single cis-diastereoisomers by the Staudinger reaction. Both cis- and trans-4-formyl-beta-lactams react with the appropriate dial or dithiol under acid catalysis to yield dioxolanes or dithiolanes, while reaction with trimethyl orthoformate or benzenethiol gave 4-acetal or thioacetal beta-lactams, respectively. Azetidines were smoothly obtained by reduction of easily available beta-lactams with monochloroalane (AlH2Cl), generated in situ from LiAlH4/AlCl3. The chemical reactivity of azetidines with AlEt2Cl was further investigated. Different substituted azetidines showed varied behavior on product formation during diethylaluminum chloride promoted reactions. Azetidines having 4-methoxyphenyl or 2-furyl groups at C2 and a benzyl or allyl substituent at nitrogen efficiently reacted with AlEt2Cl to give olefins stereoselectively through a fragmentation process, while acetal or thioacetal azetidines under the standard reaction conditions afforded in a stereocontrolled manner pyrrolidines as the sole product. Furthermore, thioacetal azetidines bearing a substituent at C3 on the azetidine ring that can promote aromatization (phenoxy or exocyclic double bond) gave pyrroles by reaction with AlEt2Cl.