(Z)-2-(p-Anisyl)-1-<(1R,2S,5R)-menthyloxy>ethene

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (Z)-2-(p-Anisyl)-1-<(1R,2S,5R)-menthyloxy>ethene
• 英文别名: 1-methoxy-4-[(Z)-2-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxyethenyl]benzene
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: WWTYYTIBLQZYOK-XXGVEJNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  4-甲氧基二氮苯甲醛 在 sodium tetrahydroborate 、 臭氧 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 14.75h， 生成 (Z)-2-(p-Anisyl)-1-<(1R,2S,5R)-menthyloxy>ethene
  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

• Solvent free synthesis of 1-alkoxyphosphonium chlorides for stereoselective multipurpose vinyl ethers
  作者：Zain Maqsood Cheema、Humaira Yasmeen Gondal、Hina Siddiqui、Muhammad Iqbal Choudhary

  DOI：10.1080/10426507.2019.1633533

  日期：2020.1.2

  Abstract An efficient solvent free method is developed for the preparation of structurally diverse 1-alkoxymethylphosphonium chlorides in high yield. One of the prepared salts derived from (1 R,2S,5R)-(−)-Menthol auxiliary was further employed for the synthesis of vinyl ethers, where up to 99% stereoselectivity was achieved. Graphical Abstract

  摘要 开发了一种高效的无溶剂方法，以高收率制备结构多样的 1-烷氧基甲基氯化鏻。一种衍生自 (1 R,2S,5R)-(-)-薄荷醇助剂的制备盐进一步用于合成乙烯基醚，实现了高达 99% 的立体选择性。图形概要
• 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.