isopropyl 2-hydroxy-4-phenylbutyrate | 130159-28-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: isopropyl 2-hydroxy-4-phenylbutyrate
• 英文别名: Propan-2-yl 2-hydroxy-4-phenylbutanoate
• CAS: 130159-28-3
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: ILZVHAZOAHPATJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯丙醛 在 二甲基硫 、 臭氧 、 lithium diisopropyl amide 作用下， 以 xylene 为溶剂， 反应 0.17h， 生成 isopropyl 2-hydroxy-4-phenylbutyrate
  参考文献：
  名称：

  1-Chloroalkyl p-tolyl sulfoxides as useful agents for homologation of carbonyl compounds: conversion of carbonyl compounds to .alpha.-hydroxy acids, esters, and amides and .alpha.,.alpha.'-dihydroxy ketones

  摘要：

  One-carbon homologation of carbonyl compounds to alpha-hydroxy acids, esters, and amides by the use of 1-chloroalkyl p-tolyl sulfoxide as a hydroxycarbonyl anion equivalent is reported. Oxidation of the vinyl chlorides, the intermediates of the above-mentioned method, with osmium tetraoxide gives alpha,alpha'-dihydroxy ketones which are found in biologically active natural products such as cortisone and adriamycin.

  DOI：

  10.1021/jo00013a011

文献信息

• METHOD FOR PREPARING LISINOPRIL INTERMEDIATE
  申请人：Zhejiang Huahai Pharmaceutical Co., Ltd

  公开号：EP3543225A1

  公开（公告）日：2019-09-25

  The invention provides a method for preparing a lisinopril intermediate, comprising: treating (R)-hydroxy-4-phenylbutyrate with sulfonyl chloride in an organic solvent in the presence of a base to obtain a solution of sulfonate; reacting the obtained solution with a salt of trifluoroacetyl lysine; and obtaining a N2-[1-(S)-alkoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysine by separating after the reaction is completed. The method for preparing lisinopril intermediate provided by the invention has a shorter synthesis route, is easy to operate, has a low cost, and is suitable for industrial production.

  本发明提供了一种赖氨普利中间体的制备方法，包括：在碱存在下，在有机溶剂中用磺酰氯处理(R)-羟基-4-苯基丁酸酯，得到磺酸盐溶液；将得到的溶液与三氟乙酰赖氨酸盐反应；反应完成后通过分离得到N2-[1-(S)-烷氧羰基-3-苯基丙基]-N6-三氟乙酰-L-赖氨酸。本发明提供的利辛普利中间体的制备方法合成路线较短，操作简便，成本较低，适合工业化生产。
• Method for preparing lisinopril intermediate
  申请人：ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTD.

  公开号：US10633329B2

  公开（公告）日：2020-04-28

  A method for preparing a lisinopril intermediate is provided. The method includes: treating (R)-hydroxy-4-phenylbutyrate with sulfonyl chloride in an organic solvent in the presence of a base to obtain a solution of sulfonate; reacting the obtained solution with a salt of trifluoroacetyl lysine; and obtaining a N2-[1-(S)-alkoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysine by separating after the reaction is completed. The method provided has a shorter synthesis route, is easy to operate, has a low cost, and is suitable for industrial production.

  本发明提供了一种制备利辛普利中间体的方法。该方法包括：在碱存在下，在有机溶剂中用磺酰氯处理(R)-羟基-4-苯基丁酸酯，得到磺酸盐溶液；将得到的溶液与三氟乙酰赖氨酸盐反应；反应完成后通过分离得到N2-[1-(S)-烷氧羰基-3-苯基丙基]-N6-三氟乙酰-L-赖氨酸。该方法合成路线短、操作简便、成本低，适合工业化生产。
• NISHINAGA, AKIRA;MARUYAMA, KAZUSHIGE;YODA, KOHEI;OKAMOTO, HIROMITSU, J. CHEM. SOC. CHEM. COMMUN.,(1990) N2, C. 876-877
  作者：NISHINAGA, AKIRA、MARUYAMA, KAZUSHIGE、YODA, KOHEI、OKAMOTO, HIROMITSU

  DOI：——

  日期：——
• SATOH, TSUYOSHI;ONDA, KEN-ICHI;YAMAKAWA, KOJI, J. ORG. CHEM., 56,(1991) N3, C. 4129-4134
  作者：SATOH, TSUYOSHI、ONDA, KEN-ICHI、YAMAKAWA, KOJI

  DOI：——

  日期：——
• 1-Chloroalkyl p-tolyl sulfoxides as useful agents for homologation of carbonyl compounds: conversion of carbonyl compounds to .alpha.-hydroxy acids, esters, and amides and .alpha.,.alpha.'-dihydroxy ketones
  作者：Tsuyoshi Satoh、Kenichi Onda、Koji Yamakawa

  DOI：10.1021/jo00013a011

  日期：1991.6

  One-carbon homologation of carbonyl compounds to alpha-hydroxy acids, esters, and amides by the use of 1-chloroalkyl p-tolyl sulfoxide as a hydroxycarbonyl anion equivalent is reported. Oxidation of the vinyl chlorides, the intermediates of the above-mentioned method, with osmium tetraoxide gives alpha,alpha'-dihydroxy ketones which are found in biologically active natural products such as cortisone and adriamycin.