cis-1-(benzyl)-4-(p-methoxyphenyl)-3-phenoxy-2-azetidinone | 97934-55-9

• 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: cis-1-(benzyl)-4-(p-methoxyphenyl)-3-phenoxy-2-azetidinone
• 英文别名: (3S,4R)-1-benzyl-4-(4-methoxyphenyl)-3-phenoxyazetidin-2-one
• CAS: 97934-55-9
• 化学式: C₂₃H₂₁NO₃
• 分子量: 359.425
• InChiKey: QBSPXNTYDLLDEY-YADHBBJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  cis-1-(benzyl)-4-(p-methoxyphenyl)-3-phenoxy-2-azetidinone 以 乙腈 为溶剂， 反应 0.75h， 生成 trans-1-(benzyl)-4-(p-methoxyphenyl)-3-phenoxy-2-azetidinone
  参考文献：
  名称：

  Alcazar, Roberto; Ramirez, Pedro; Vicente, Ruben, Heterocycles, 2001, vol. 55, # 3, p. 511 - 521

  摘要：

  DOI：
• 作为产物：
  描述：

  N-benzyl-1-(4-methoxyphenyl)methanimine 、 苯氧乙酸 在 二氯磷酸苯酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以84%的产率得到cis-1-(benzyl)-4-(p-methoxyphenyl)-3-phenoxy-2-azetidinone
  参考文献：
  名称：

  苯基二氯磷酸试剂诱导的乙酸和亚胺的合成β-内酰胺

  摘要：

  描述了从丹尼盐和席夫碱制备乙烯基氨基-β-内酰胺的实用方法的开发。在已知可从亚胺和乙酸生产β-内酰胺的试剂中，只有苯基二氯磷酸酯和1-甲基-2-氯吡啶碘代碘适合用于合成乙烯基氨基-β-内酰胺。乙酸与由二氯磷酸苯酯促进的乙醇亚胺衍生物反应生成恶唑烷，而不是β-内酰胺。在起始席夫碱中保护羟基作为三甲基甲硅烷基醚提供了通往相应的β-内酰胺而不是恶唑烷的便利途径。对该方法的范围进行了一些观察。

  DOI：

  10.1016/s0040-4020(01)96484-1

文献信息

• 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。
• New intramolecular cyclization and rearrangement processes based on the radical aryl-aryl coupling of arylsubstituted 2-azetidinones
  作者：Benito Alcaide、Alberto Rodríguez-Vicente

  DOI：10.1016/s0040-4039(98)01373-2

  日期：1998.9

  2-azetidinones having fused or not biaryl units are easily prepared by the tin-mediated, intramolecular aryl-aryl radical cyclization of readily available arylsubstituted 2-azetidinones. The regioselectivity and efficiency of the process is determined both by the length of the linking chain through the β-lactam nucleus and by the number and position of the substituents on the aromatic acceptor ring.

  通过容易获得的芳基取代的2-氮杂环丁酮的锡介导的分子内芳基-芳基自由基环化，可以容易地制备具有稠合或不具有联芳基单元的新的多环2-氮杂环丁酮。该方法的区域选择性和效率既取决于通过β-内酰胺核的连接链的长度，也取决于芳族受体环上取代基的数量和位置。
• 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.
• Thermally Induced Isomerization of <i>cis</i>-1,3,4-Trisubstituted 2-Azetidinones
  作者：Benito Alcaide、Pedro Almendros、Nati R. Salgado、Alberto Rodríguez-Vicente

  DOI：10.1021/jo000229x

  日期：2000.7.1
• Syntheses of β-lactams from acetic acids and imines induced by phenyl dichlorophosphate reagent
  作者：Ana Arrieta、Fernando P. Cossio、Claudio Palomo

  DOI：10.1016/s0040-4020(01)96484-1

  日期：——

  Among the reagents known to produce β-lactams from imines and acetic acids, only phenyl dichlorophosphate and 1-methyl-2-chloropyridinium iodide are suitable for the synthesis of vinylamino- β-lactams. Reaction of acetic acids with ethanolimine derivatives promoted by phenyl dichlorophosphate affords oxazolidines instead β-lactams. Protection of the hydroxyl group as the trimethylsilyl ether in the

  描述了从丹尼盐和席夫碱制备乙烯基氨基-β-内酰胺的实用方法的开发。在已知可从亚胺和乙酸生产β-内酰胺的试剂中，只有苯基二氯磷酸酯和1-甲基-2-氯吡啶碘代碘适合用于合成乙烯基氨基-β-内酰胺。乙酸与由二氯磷酸苯酯促进的乙醇亚胺衍生物反应生成恶唑烷，而不是β-内酰胺。在起始席夫碱中保护羟基作为三甲基甲硅烷基醚提供了通往相应的β-内酰胺而不是恶唑烷的便利途径。对该方法的范围进行了一些观察。