(Z)-2-(p-methoxyphenyl)-1-phenoxyethene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-2-(p-methoxyphenyl)-1-phenoxyethene
• 英文别名: (Z)-2-(p-Anisyl)-1-phenoxyethene；1-methoxy-4-[(Z)-2-phenoxyethenyl]benzene
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: HIBHQBBBWLFOKH-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  cis-1-(benzyl)-4-(p-methoxyphenyl)-3-phenoxy-2-azetidinone 在 lithium aluminium tetrahydride 、 三氯化铝 、 氯化二乙基铝 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (Z)-2-(p-methoxyphenyl)-1-phenoxyethene
  参考文献：
  名称：

  AlEt 2 Cl促进氮杂环丁烷环的新断裂和重排反应

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(97)10577-9

文献信息

• Pyrolysis of azetidinone derivatives: a versatile route towards electron-rich alkenes, C-1 allylation and/or homologation of aldehydes
  作者：Nouf S. Al-Hamdan、Osama M. Habib、Yehia A. Ibrahim、Nouria A. Al-Awadi、Osman M. E. El-Dusouqui

  DOI：10.1039/c4ra01024h

  日期：——

  β-thiolactams led essentially to stereoselective synthesis of the high energy electron-rich Z-alkenes. Extension of this methodology to the pyrolysis of 3-allyloxy derivatives gave a simple direct route to the synthetically important 4-pentenal. These pyrolytic transformations convert aldehydes to aryloxyalkenes (a protected homologation) and 4-pentenal (a C-1 allylation and homologation). The starting

  β-内酰胺和β-硫代内酰胺的热解基本上导致了高能富电子的Z-烯烃的立体选择性合成。将该方法扩展至3-烯丙氧基衍生物的热解，给出了一条通往合成重要的4-戊烯醛的简单直接途径。这些热解转化将醛转化为芳氧基烯烃（受保护的同系物）和4-戊烯醛（C-1烯丙基化和同系物）。起始的3-芳氧基和3-烯丙氧基-β-内酰胺是通过标准的Staudinger乙烯酮-亚胺[2 + 2]环加成反应合成的。通过用Lawesson试剂对β-内酰胺进行硫杂化，可以容易地以高收率获得相应的β-硫内酰胺。
• Stereoselective Synthesis of Vinyl Ethers by the Reaction of N-(Arylidene(or alkylidene)amino)-2-azetidinones with Ozone
  作者：Benito Alcaide、Javier Perez-Castells、Concepcion Polanco、Miguel A. Sierra

  DOI：10.1021/jo00124a008

  日期：1995.9

  Ozonolysis of N-(arylidene(or alkylidene)amino)-2-azetidinones followed by NaBH4 workup yields enol ethers in good yields with high levels of stereoselectivity. Di- and trisubstituted olefin derivatives are available through this procedure. Chiral 2-azetidinones lead to enol ethers with a chiral moiety without racemization. The reaction is thought to occur through a novel B-type fragmentation of the 2-azetidinone ring. This process is closely related to the well-known N-nitrosoamide to ester rearrangement and the decarboxylation of oxetan-2-ones.
• 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.