(E)-octan-2-yl 3-(3,4,5-trimethoxyphenyl)acrylate | 1160843-01-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-octan-2-yl 3-(3,4,5-trimethoxyphenyl)acrylate
• 英文别名: octan-2-yl (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
• CAS: 1160843-01-5
• 化学式: C₂₀H₃₀O₅
• 分子量: 350.455
• InChiKey: KTDJZRYNDARYIZ-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  octan-2-yl N,N'-di(propan-2-yl)carbamimidate 、 3,4,5-三甲氧基肉桂酸 以 乙腈 为溶剂， 反应 0.08h， 以74%的产率得到(E)-octan-2-yl 3-(3,4,5-trimethoxyphenyl)acrylate
  参考文献：
  名称：

  Microwave-Assisted Ester Formation Using O-Alkylisoureas: A Convenient Method for the Synthesis of Esters with Inversion of Configuration

  摘要：

  The formation of carboxylic esters via reaction of carboxylic acids with O-alkylisoureas proceeds in excellent yields with very short reaction times when conducted in a monomode microwave synthesizer. Efficient processes were developed using preformed or commercially available isoureas derived from primary and secondary alcohols, with a reaction time of only 5 min or less. It was demonstrated that under these microwave conditions, ester formation proceeded in good yields with clean inversion of configuration where appropriate. The process was validated using menthol, a hindered substrate for S(N)2 reactions. In addition, starting from primary alcohols, ester formation was successfully accomplished using ail in situ isourea formation procedure. A polymer-assisted solution-phase procedure was also developed by employing preformed solid-supported isoureas and by an efficient "catch and release" ester formation procedure whereby primary alcohols were caught on resin as isoureas by reaction with immobilized carbodiimide and released as esters by subsequent treatment with a carboxylic acids.

  DOI：

  10.1021/jo900476y

文献信息

• Microwave-Assisted Ester Formation Using <i>O</i>-Alkylisoureas: A Convenient Method for the Synthesis of Esters with Inversion of Configuration
  作者：Alessandra Chighine、Stefano Crosignani、Marie-Claire Arnal、Mark Bradley、Bruno Linclau

  DOI：10.1021/jo900476y

  日期：2009.7.3

  The formation of carboxylic esters via reaction of carboxylic acids with O-alkylisoureas proceeds in excellent yields with very short reaction times when conducted in a monomode microwave synthesizer. Efficient processes were developed using preformed or commercially available isoureas derived from primary and secondary alcohols, with a reaction time of only 5 min or less. It was demonstrated that under these microwave conditions, ester formation proceeded in good yields with clean inversion of configuration where appropriate. The process was validated using menthol, a hindered substrate for S(N)2 reactions. In addition, starting from primary alcohols, ester formation was successfully accomplished using ail in situ isourea formation procedure. A polymer-assisted solution-phase procedure was also developed by employing preformed solid-supported isoureas and by an efficient "catch and release" ester formation procedure whereby primary alcohols were caught on resin as isoureas by reaction with immobilized carbodiimide and released as esters by subsequent treatment with a carboxylic acids.