ethyl (2Z)-2-ethoxy-3-(4-hydroxyphenyl)acrylate | 70680-30-7

• 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: ethyl (2Z)-2-ethoxy-3-(4-hydroxyphenyl)acrylate
• 英文别名: ethyl (Z)-2-ethoxy-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 70680-30-7
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: DGFSKUGOWGALBG-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  ethyl (2Z)-2-ethoxy-3-(4-hydroxyphenyl)acrylate 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 12.0h， 生成 ethyl 2-ethoxy-3-(4-(2-(3-methoxyphenyl)-2-oxoethoxy)phenyl)propanoate
  参考文献：
  名称：

  [EN] PPAR-SPARING THIAZOLIDINEDIONES AND COMBINATIONS FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES
  [FR] THIAZOLIDINEDIONES ÉPARGNANT LES PPAR ET ASSOCIATIONS POUR LE TRAITEMENT DE MALADIES NEURODÉGÉNÉRATIVES

  摘要：

  公开号：

  WO2014093114A8

文献信息

• [EN] PROCESS FOR PRODUCING OPTICALLY ACTIVE 3-(4-HYDROXYPHENYL)PROPIONIC ACIDS<br/>[FR] PROCEDE DE PRODUCTION D'ACIDES 3-(4-HYDROXYPHENYL)PROPIONIQUES OPTIQUEMENT ACTIFS
  申请人：TAKASAGO PERFUMERY CO LTD

  公开号：WO2005051882A1

  公开（公告）日：2005-06-09

  The present invention relates to a process for producing an optically active 3-(4-hydroxyphenyl)propionic acid useful as intermediates for medicines, through short steps in good yield and with high optical purity. More specifically, the present invention relates to a process for producing an optically active 3-(4-hydroxyphenyl)propionic acid of the formula (6): wherein R2 is an alkyl group; R5 to R8 are each independently a hydrogen atom or a substituent; and the symbol * is an chiral carbon atom, or a salt thereof, which comprises reacting a benzaldehyde of the formula (1): wherein R1 is a protective group; and R5 to R8 are each the same as defined above, with a glycolic acid derivative of the formula (2): wherein R3 is a hydrocarbon group; and R2 is the same as defined above, hydrolyzing the resulting product to give a cinnamic acid of the formula (4): wherein R1, R2 and R5 to R8 are each the same as defined above, or a salt thereof, and subjecting the resulting cinnamic acid (4) or a salt thereof to asymmetric hydrogenation to give an optically active phenylpropionic acid of the formula (5): wherein all the symbols are each the same as defined above, or a salt thereof, followed by deprotection.

  本发明涉及一种生产光学活性3-(4-羟基苯基)丙酸的工艺，作为药物中间体，通过简短的步骤、高产率和高光学纯度。更具体地，本发明涉及一种生产光学活性3-(4-羟基苯基)丙酸的工艺，其化学结构如下（6）：其中R2是烷基；R5至R8分别独立地是氢原子或取代基；符号*是一个手性碳原子，或其盐，包括将化学结构如下（1）的苯甲醛：其中R1是保护基；R5至R8分别与上述定义相同，与化学结构如下（2）的甘醇酸衍生物反应：其中R3是烃基；R2与上述定义相同，水解得到肉桂酸的产物：其中R1、R2和R5至R8分别与上述定义相同，或其盐，并将得到的肉桂酸（4）或其盐进行不对称氢化反应，得到光学活性苯丙酸的产物：其中所有符号均与上述定义相同，或其盐，随后进行去保护处理。
• Process for producing optically active 3-(4-hydroxyphenyl)proprionic acids
  申请人：Yokozawa Tohru

  公开号：US20070142472A1

  公开（公告）日：2007-06-21

  The present invention relates to a process for producing an optically active 3-(4-hydroxyphenyl)propionic acid useful as intermediates for medicines, through short steps in good yield and with high optical purity. More specifically, the present invention relates to a process for producing an optically active 3-(4-hydroxyphenyl)propionic acid of the formula (6): wherein R 2 is an alkyl group; R 5 to R 8 are each independently a hydrogen atom or a substituent; and the symbol * is an chiral carbon atom, or a salt thereof, which comprises reacting a benzaldehyde of the formula (1): wherein R 1 is a protective group; and R 5 to R 8 are each the same as defined above, with a glycolic acid derivative of the formula (2): wherein R 3 is a hydrocarbon group; and R 2 is the same as defined above, hydrolyzing the resulting product to give a cinnamic acid of the formula (4): wherein R 1 , R 2 and R 5 to R 8 are each the same as defined above, or a salt thereof, and subjecting the resulting cinnamic acid (4) or a salt thereof to asymmetric hydrogenation to give an optically active phenylpropionic acid of the formula (5): wherein all the symbols are each the same as defined above, or a salt thereof, followed by deprotection.

  本发明涉及一种生产光学活性的3-(4-羟基苯基)丙酸的方法，该方法通过短步骤以良好产率和高光学纯度的方式，作为药物中间体。更具体地说，本发明涉及一种生产式(6)的光学活性3-(4-羟基苯基)丙酸的方法：其中R2是烷基；R5到R8分别独立地是氢原子或取代基；符号*是手性碳原子，或其盐，包括用式(1)的苯甲醛反应：其中R1是保护基；R5到R8分别与上述定义相同，与式(2)的乙二醇酸衍生物反应：其中R3是碳氢基团；R2与上述定义相同，水解所得产物得到式(4)的肉桂酸：其中R1、R2和R5到R8分别与上述定义相同，或其盐，并将所得的肉桂酸(4)或其盐经过不对称氢化作用得到式(5)的光学活性苯丙酸：其中所有符号均与上述定义相同，或其盐，然后去保护基。
• PPAR-SPARING THIAZOLIDINEDIONES AND COMBINATIONS FOR THE TREATMENT OF NEURODEGENERATIVE AND OTHER METABOLIC DISEASES
  申请人：METABOLIC SOLUTIONS DEVELOPMENT COMPANY LLC

  公开号：US20160051529A1

  公开（公告）日：2016-02-25

  The present invention relates to PPARy-sparing compounds and pharmaceutical compositions formulated with such compounds that are useful for treating, delaying the onset of, or reducing the symptoms of a neurodegenerative disorder including Huntington's disease, epilepsy, AMS, and MS.

  本发明涉及PPARy-sparing化合物和与这些化合物配制的药物组合物，其可用于治疗、延缓或减轻神经退行性疾病的症状，包括亨廷顿病、癫痫、AMS和MS。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE 3-(4-HYDROXYPHENYL)PROPIONIC ACIDS
  申请人：Takasago International Corporation

  公开号：EP1687250A1

  公开（公告）日：2006-08-09
• [EN] PPAR-SPARING THIAZOLIDINEDIONES AND COMBINATIONS FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES<br/>[FR] THIAZOLIDINEDIONES ÉPARGNANT LES PPAR ET ASSOCIATIONS POUR LE TRAITEMENT DE MALADIES NEURODÉGÉNÉRATIVES
  申请人：METABOLIC SOLUTIONS DEV CO LLC

  公开号：WO2014093114A8

  公开（公告）日：2014-10-09