3-(4-hydroxyphenyl)-2-methoxypropionic acid cyclohexylamine salt

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(4-hydroxyphenyl)-2-methoxypropionic acid cyclohexylamine salt
• 英文别名: Cyclohexylazanium;3-(4-hydroxyphenyl)-2-methoxypropanoate
• 化学式: C₆H₁₃N*C₁₀H₁₂O₄
• 分子量: 295.379
• InChiKey: DPNHXYUUJZBYCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.26
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  97.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  p-Hydroxy-α-methoxyzimtsaeure 、 环己胺 在 [Ru(p-cymene)((S)-dm-segphos)]Cl 氢气 作用下， 以 甲醇 为溶剂， 80.0 ℃ 、4.0 MPa 条件下， 反应 16.0h， 以98%的产率得到
  参考文献：
  名称：

  [EN] PROCESS FOR PRODUCING OPTICALLY ACTIVE 3-(4-HYDROXYPHENYL)PROPIONIC ACIDS
  [FR] PROCEDE DE PRODUCTION D'ACIDES 3-(4-HYDROXYPHENYL)PROPIONIQUES OPTIQUEMENT ACTIFS

  摘要：

  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。

  公开号：

  WO2005051882A1

文献信息

• 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。
• 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] 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。