S-methyl (Z)-2-ethoxy-3-(4-methoxyphenyl)-2-propenthioate | 1333382-79-8

• 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: S-methyl (Z)-2-ethoxy-3-(4-methoxyphenyl)-2-propenthioate
• CAS: 1333382-79-8
• 化学式: C₁₃H₁₆O₃S
• 分子量: 252.334
• InChiKey: MEDAHKUJFJGGBB-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  甲硫醇 、 2-Ethoxy-3-(4-methoxyphenyl)prop-2-enoic acid 在 草酰氯 、 吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以85%的产率得到S-methyl (Z)-2-ethoxy-3-(4-methoxyphenyl)-2-propenthioate
  参考文献：
  名称：

  Biotechnological Development of a Practical Synthesis of Ethyl (S)-2-Ethoxy-3-(p-methoxyphenyl)propanoate (EEHP): Over 100-Fold Productivity Increase from Yeast Whole Cells to Recombinant Isolated Enzymes

  摘要：

  The coupling of the enantioselective reduction catalyzed by Old Yellow Enzymes (OYEs), together with the in situ substrate feeding product removal (SFPR) concept, significantly improved the productivity of the g-scale preparation of ethyl (S)-2ethoxy-3-(p-methoxyphenyl)propanoate (EEHP), an important precursor of several PPAR-alpha/gamma agonists, such as Tesaglitazar. The OYEs and the glucose dehydrogenase for cofactor regeneration were cloned, overexpressed in Escherichia coli, and purified. The synthetic sequence was completed by a NaClO2 oxidation employing cheap and environmentally friendly conditions. The product was obtained in 94% yield and with an ee of 98% over the two steps.

  DOI：

  10.1021/op200085k