ethyl (S)-2-ethoxy-3-(4-methoxyphenyl)propanoate | 808123-66-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl (S)-2-ethoxy-3-(4-methoxyphenyl)propanoate
• 英文别名: Ethyl (s)-2-ethoxy-3-(p-methoxyphenyl)propanoate；ethyl (2S)-2-ethoxy-3-(4-methoxyphenyl)propanoate
• CAS: 808123-66-2
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: ALKJSBOBFFBVSV-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (S)-2-ethoxy-3-(4-methoxyphenyl)propanoate 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以96%的产率得到(S)-2-乙氧基-3-(4-甲氧基苯基)丙酸
  参考文献：
  名称：

  Enzyme-mediated synthesis of EEHP and EMHP, useful pharmaceutical intermediates of PPAR agonists

  摘要：

  A new scaleable synthetic route to the title compounds has been developed. The reaction pathway is based on the alpha-chymotrypsin-catalysed hydrolysis of the racemic ethyl 2-ethoxy-3-(p-methoxyphenyl)propanoate or of the racemic ethyl 2-methoxy-3-(p-methoxyphenyl)propanoate to give the corresponding resolved (S)-esters with excellent ee. The acids were easily separated from the (S)-esters by a simple acid-base work-up. The overall yields of 1 and 2 were 16% and 17%, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.013
• 作为产物：
  描述：

  溴乙烷 、 ethyl (S)-2-hydroxy-3-(4-methoxyphenyl)propanoate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.25h， 以79%的产率得到ethyl (S)-2-ethoxy-3-(4-methoxyphenyl)propanoate
  参考文献：
  名称：

  Enzyme-mediated synthesis of EEHP and EMHP, useful pharmaceutical intermediates of PPAR agonists

  摘要：

  A new scaleable synthetic route to the title compounds has been developed. The reaction pathway is based on the alpha-chymotrypsin-catalysed hydrolysis of the racemic ethyl 2-ethoxy-3-(p-methoxyphenyl)propanoate or of the racemic ethyl 2-methoxy-3-(p-methoxyphenyl)propanoate to give the corresponding resolved (S)-esters with excellent ee. The acids were easily separated from the (S)-esters by a simple acid-base work-up. The overall yields of 1 and 2 were 16% and 17%, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.013