2-Ethoxy-3-(4-methoxyphenyl)prop-2-enoic acid | 343793-37-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Ethoxy-3-(4-methoxyphenyl)prop-2-enoic acid
• CAS: 343793-37-3
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: BXRXMFJGQDFTTN-UHFFFAOYSA-N

物化性质

• 沸点：
  373.1±32.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Ethoxy-3-(4-methoxyphenyl)prop-2-enoic acid 在 di-μ-chlorobis(norbornadiene)dirhodium(I) 、 C₄₂H₅₅Fe₂NP₂ 、 氢气 作用下， 20.0 ℃ 、2.03 MPa 条件下， 反应 20.0h， 以97%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：

  Highly enantioselective hydrogenation of α-oxy functionalized α,β-unsaturated acids catalyzed by a ChenPhos–Rh complex in CF₃CH₂OH

  摘要：

  一种Chenphos-Rh络合物被证明是α-氧基化α，β-不饱和羧酸的不对称加氢反应的高效催化剂，通过配体和底物之间的离子相互作用。

  DOI：

  10.1039/c5cc09089j

文献信息

• Biotechnological Development of a Practical Synthesis of Ethyl (<i>S</i>)-2-Ethoxy-3-(<i>p</i>-methoxyphenyl)propanoate (EEHP): Over 100-Fold Productivity Increase from Yeast Whole Cells to Recombinant Isolated Enzymes
  作者：Matthias Bechtold、Elisabetta Brenna、Christian Femmer、Francesco G. Gatti、Sven Panke、Fabio Parmeggiani、Alessandro Sacchetti

  DOI：10.1021/op200085k

  日期：2012.2.17

  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.