(S)-2-Hydroxy-3-(4-methoxyphenyl)propionsaeure | 33173-34-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-2-Hydroxy-3-(4-methoxyphenyl)propionsaeure
• 英文别名: p-methoxy-L-phenyllactic acid；2-hydroxy-3-(4-methoxyphenyl)propanoic acid；(S)-2-hydroxy-3-(4-methoxyphenyl) propanoic acid；Latifolicinin D；(2S)-2-hydroxy-3-(4-methoxyphenyl)propanoic acid
• CAS: 33173-34-1
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: GEDLJGYFEOYKEG-VIFPVBQESA-N

物化性质

• 沸点：
  372.9±27.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溴乙烷 、 (S)-2-Hydroxy-3-(4-methoxyphenyl)propionsaeure 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 以100%的产率得到ethyl (S)-2-hydroxy-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
• 作为产物：
  描述：

  4-甲氧基-L-苯丙氨酸 在 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 48.0h， 生成 4-Methoxy-tropasaeure 、 (S)-2-Hydroxy-3-(4-methoxyphenyl)propionsaeure
  参考文献：
  名称：

  Wuensch, Bernhard; Zott, Matthias, Liebigs Annalen der Chemie, 1992, # 1, p. 39 - 46

  摘要：

  DOI：

文献信息

• PROCESS FOR PRODUCING OPTICALLY ACTIVE 2-SUBSTITUENT-OXY-3-(4-SUBSTITUENT-OXYPHENYL)­PROPIONIC ACID DERIVATIVE
  申请人：Kaneka Corporation

  公开号：EP1801224A1

  公开（公告）日：2007-06-27

  The present invention relates to a process for producing an optically active 2-substituent-oxy-3-(4-substituent-oxyphenyl)propionic acid derivative which comprises stereoselectively reducing an 2-oxo-3-(4-substituent-oxyphenyl)propionic acid by an enzyme and subjecting the thus-obtained optically active 2-hydroxy-3-(4'-substituent-oxyphenyl)propionic acid to esterification of the carboxyl group according to need, then to alkylation of the hydroxyl group and, if necessary, to deprotection of an ether type protective group. The present invention may make it possible to produce an optically active 2-subsituent-oxy-3-(4-substituent-oxyphenyl)propionic acid derivative, which is useful as intermediates for the synthesis of medicinal compounds, efficiently, in a simple and easy manner, and commercially advantageously.

  本发明涉及一种生产具有光学活性的2-取代氧基-3-(4-取代氧基苯基)丙酸衍生物的方法，包括通过酶对2-氧基-3-(4-取代氧基苯基)丙酸进行立体选择性还原，然后将得到的光学活性2-羟基-3-(4'-取代氧基苯基)丙酸根据需要酯化羧基，接着烷基化羟基，必要时去除醚型保护基。本发明可能能够以简单、易操作且具有商业优势的方式高效生产用于合成药物化合物的有用中间体——具有光学活性的2-取代氧基-3-(4-取代氧基苯基)丙酸衍生物。
• Claisen Condensation as a Facile Route to an α-Alkoxy-cinnamate:  Synthesis of Ethyl (2<i>S</i>)-2-Ethoxy-3-(4-hydroxyphenyl)propanoate
  作者：Mats T. Linderberg、Mikael Moge、Sivaprasad Sivadasan

  DOI：10.1021/op040006z

  日期：2004.11.1

  The title compound was prepared from p-anisaldehyde and ethyl ethoxyacetate via a racemic synthetic route. The synthesis involves a Claisen-type condensation in which the elimination was unexpected...

  标题化合物由对茴香醛和乙氧基乙酸乙酯通过外消旋合成路线制备。该合成涉及克莱森型缩合，其中消除是出乎意料的......
• Process for Producing Optically Active 2-Substituent-Oxy-3-(4-Substituent-Oxyphenyl) Propionic Acid Derivative
  申请人：Honda Tatsuya

  公开号：US20090029429A1

  公开（公告）日：2009-01-29

  The present invention relates to a process for producing an optically active 2-substituent-oxy-3-(4-substituent-oxyphenyl)propionic acid derivative which comprises stereoselectively reducing an 2-oxo-3-(4-substituent-oxyphenyl)propionic acid by an enzyme and subjecting the thus-obtained optically active 2-hydroxy-3-(4-substituent-oxyphenyl)propionic acid to esterification of the carboxyl group according to need, then to alkylation of the hydroxyl group and, if necessary, to deprotection of an ether type protective group. The present invention may make it possible to produce an optically active 2-substituent-oxy-3-(4-substituent-oxyphenyl)propionic acid derivative, which is useful as intermediates for the synthesis of medicinal compounds, efficiently, in a simple and easy manner, and commercially advantageously.

  本发明涉及一种制备光学活性的2-取代氧基-3-(4-取代氧基苯基)丙酸衍生物的方法，其包括通过酶对2-氧代-3-(4-取代氧基苯基)丙酸进行立体选择性还原，然后对得到的光学活性的2-羟基-3-(4-取代氧基苯基)丙酸根据需要进行羧基酯化，然后进行烷基化羟基，如有必要，则进行醚型保护基的去保护。本发明可以使得在简单、易行和商业上有优势的情况下高效地制备出用于合成药物化合物的光学活性的2-取代氧基-3-(4-取代氧基苯基)丙酸衍生物。
• Enzyme-mediated synthesis of EEHP and EMHP, useful pharmaceutical intermediates of PPAR agonists
  作者：Elisabetta Brenna、Claudio Fuganti、Francesco G. Gatti、Fabio Parmeggiani

  DOI：10.1016/j.tetasy.2009.10.013

  日期：2009.11

  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.
• Wuensch, Bernhard; Zott, Matthias, Liebigs Annalen der Chemie, 1992, # 1, p. 39 - 46
  作者：Wuensch, Bernhard、Zott, Matthias

  DOI：——

  日期：——