1-[2-(benzyloxy)ethenyl]-4-methoxybenzene | 145654-55-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[2-(benzyloxy)ethenyl]-4-methoxybenzene
• 英文别名: 1-[2-(benzyloxy)vinyl]-4-methoxybenzene；(E)-2-(p-Anisyl)-1-(benzyloxy)ethene；1-methoxy-4-[(E)-2-phenylmethoxyethenyl]benzene
• CAS: 145654-55-3
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: YHNXWSGWYYKPRK-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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-4-p-Anisyl-1-<(4'-methoxybenzylidene)amino>-3-benzyloxy-2-azetidinone 在 sodium tetrahydroborate 、 臭氧 作用下， 生成 1-[2-(benzyloxy)ethenyl]-4-methoxybenzene 、 1-[2-(benzyloxy)ethenyl]-4-methoxybenzene
  参考文献：
  名称：

  Stereoselective Synthesis of Vinyl Ethers by the Reaction of N-(Arylidene(or alkylidene)amino)-2-azetidinones with Ozone

  摘要：

  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.

  DOI：

  10.1021/jo00124a008

文献信息

• Synthesis of Enol Ethers and Enamines by Pd-Catalyzed Tosylhydrazide-Promoted Cross-Coupling Reactions
  作者：José Barluenga、María Escribano、Patricia Moriel、Fernando Aznar、Carlos Valdés

  DOI：10.1002/chem.200902718

  日期：2009.12.14

  α‐Alkoxycarbonyl and α‐aminocarbonyl compounds are good substrates for the recently developed tosylhydrazide‐promoted Pd‐catalyzed cross‐coupling of carbonyls with aryl halides. The reaction gives rise to enol ethers and enamines, respectively, which are useful synthetic intermediates in heterocyclic synthesis. Otherwise, they can be hydrolyzed to give α,α‐disubstituted aldehydes.

  α-取代很好：α-烷氧羰基和α-氨基羰基化合物是最近开发的甲苯磺酰肼促进的Pd催化的羰基与芳基卤化物交叉偶联的良好底物。该反应分别产生烯醇醚和烯胺，它们是杂环合成中有用的合成中间体。否则，可以将它们水解得到α，α-二取代醛。
• Selective Approaches to α‐ and β‐Arylated Vinyl Ethers
  作者：Anna Domzalska‐Pieczykolan、Ignacio Funes‐Ardoiz、Bartłomiej Furman、Carsten Bolm

  DOI：10.1002/anie.202109801

  日期：2022.1.3

  Benzyl vinyl ethers have selectively been arylated at either α or β position by fine-tuned Heck-type palladium catalyses. In contrast to previous protocols, no excess of arylating reagent or substrate chelation is necessary. For achieving good yields and high α/β-selectivities various factors determining the catalytic system had to be optimized. The results of DFT computational studies correlate selectivity

  苄基乙烯基醚已通过微调的 Heck 型钯催化剂在 α 或 β 位选择性芳基化。与以前的协议相比，不需要过量的芳基化试剂或底物螯合。为了获得良好的收率和高 α/β-选择性，必须优化决定催化体系的各种因素。DFT 计算研究的结果将选择性与 Pd 中心上的电子丰富度相关联。
• A novel fragmentation of the .beta.-lactam ring: stereoselective entry to vinyl ethers by reaction of N-(arylidene(or alkylidene)amino)-2-azetidinones with ozone
  作者：Benito Alcaide、Miguel Miranda、Javier Perez-Castells、Miguel A. Sierra

  DOI：10.1021/jo00054a003

  日期：1993.1

  The title compounds undergo a novel 2-azetidinone ring fragmentation by reaction with ozone followed by NaBH4 workup to stereoselectively yield vinyl ethers via intermediate N-nitroso-beta-lactams.
• 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.