3-(4-benzyloxyphenyl)-2-hydroxypropionic acid isopropyl ester | 481072-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-benzyloxyphenyl)-2-hydroxypropionic acid isopropyl ester
• 英文别名: propan-2-yl (2S)-2-hydroxy-3-(4-phenylmethoxyphenyl)propanoate
• CAS: 481072-42-8
• 化学式: C₁₉H₂₂O₄
• 分子量: 314.381
• InChiKey: JWOPOYHFSIJTTK-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  3-(4-benzyloxyphenyl)-2-hydroxypropionic acid isopropyl ester 、 碘乙烷 在 sodium tert-pentoxide 、 溶剂黄146 作用下， 以 DMF (N,N-dimethyl-formamide) 、 甲苯 为溶剂， 反应 3.25h， 以90%的产率得到compound 5
  参考文献：
  名称：

  [EN] AMIDE LINKER PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR MODULATORS
  [FR] MODULATEURS DE RECEPTEUR ACTIVE DE LA PROLIFERATION DES PEROXISOMES A LIEUR AMIDE

  摘要：

  本发明涉及结构式(I)的化合物、组合物及其使用。

  公开号：

  WO2004000789A1
• 作为产物：
  描述：

  4-羟苯基丙酮酸 在 sodium hydroxide 、 硫酸 、 potassium carbonate 、 三乙胺 、 (+)-二异松蒎基氯硼烷 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 26.0h， 生成 3-(4-benzyloxyphenyl)-2-hydroxypropionic acid isopropyl ester
  参考文献：
  名称：

  Synthesis of a Peroxime Proliferator Activated Receptor (PPAR) α/γ Agonist via Stereocontrolled Williamson Ether Synthesis and Stereospecific S_N2 Reaction of S-2-Chloro Propionic Acid with Phenoxides

  摘要：

  The stereospecific synthesis of the PPAR alpha/gamma agonist I was accomplished via ethylation of the optically pure tribydroxy derivative 6, itself derived via an enzymatic resolution. The ethylation can be accomplished without epimerization only under strict control of the reaction conditions and the choice of base (sodium tert-amylate), temperature (-30 degrees C), order of addition, and solvent (DMF). The key diastereospecific S(N)2 reaction of the phenol 4 with S-2-chloropropionic acid is best achieved via the sodium phenoxide of 4 derived from Na-0 as the reagent of choice. The structure elucidation and key purification protocols to achieve pharmaceutical purity will also be described.

  DOI：

  10.1021/jo050268e

文献信息

• 3-Aryl-A-oxy substituted propanoic acids and a process for their preparation
  申请人：——

  公开号：US20040248849A1

  公开（公告）日：2004-12-09

  The present invention relates to novel antidiabetic compounds, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs and pharmaceutically acceptable compositions containing them. More particularly, the present invention relates to novel 3-aryl-&agr;-oxy substituted propanoic acids of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs and pharmaceutically acceptable compositions containing them. Formula (I) where R 1 represents t-butyldimethyl silyl, trimethyl silyl or alkoxyalkyl group; R 2 represents hydrogen or substituted or unsubstituted (C 1 -C 6 )alkyl group. 1

  本发明涉及新型抗糖尿病化合物及其衍生物、类似物、互变异构体、立体异构体、多晶形式和药学上可接受的含有它们的组合物。更具体地，本发明涉及一般式（I）的新型3-芳基-&agr;-氧基取代的丙酸类化合物，其衍生物、类似物、互变异构体、立体异构体、多晶形式和药学上可接受的含有它们的组合物。其中，式（I）中，R1表示叔丁基二甲基硅基、三甲基硅基或烷氧基烷基；R2表示氢或取代或未取代的（C1-C6）烷基。
• [EN] 3-ARYL- DOLLAR G(a)-OXY SUBSTITUTED PROPANOIC ACIDS AND A PROCESS FOR THEIR PREPARATION<br/>[FR] ACIDES PROPANOIQUES SUBSTITUES PAR 3-ARYL- DOLLAR G(a)-OXY ET LEUR PROCEDE DE PREPARATION
  申请人：REDDY RESEARCH FOUNDATION

  公开号：WO2003002575A1

  公开（公告）日：2003-01-09

  The present invention relates to novel antidiabetic compounds, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs and pharmaceutically acceptable compositions containing them. More particularly, the present invention relates to novel 3-aryl-α-oxy substituted propanoic acids of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs and pharmaceutically acceptable compositions containing them. Formula (I) where R1 represents t-butyldimethyl silyl, trimethyl silyl or alkoxyalkyl group; R2 represents hydrogen or substituted or unsubstituted (C¿1?-C6)alkyl group.
• [EN] IMPROVED PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE PHENOXAZINE DERIVATIVES AS ANTIDIABETIC AGENTS<br/>[FR] PERFECTIONNEMENT D'UN PROCEDE D'ELABORATION DE DERIVES PHENOXAZINE OPTIQUEMENT ACTIFS UTILISABLES COMME AGENTS ANTIDIABETIQUES
  申请人：REDDYS LAB LTD DR

  公开号：WO2003027084A1

  公开（公告）日：2003-04-03

  The present invention relates to improved process for the preparation of antidiabetic compound having the formula (1). where R1 represents alkyl group such as methyl, ethyl, propyl, isopropyl and the like.
• [EN] AMIDE LINKER PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR MODULATORS<br/>[FR] MODULATEURS DE RECEPTEUR ACTIVE DE LA PROLIFERATION DES PEROXISOMES A LIEUR AMIDE
  申请人：LILLY CO ELI

  公开号：WO2004000789A1

  公开（公告）日：2003-12-31

  The present invention is directed to compounds, compositions, and use of compounds the structural Formula (I).

  本发明涉及结构式(I)的化合物、组合物及其使用。
• Synthesis of a Peroxime Proliferator Activated Receptor (PPAR) α/γ Agonist via Stereocontrolled Williamson Ether Synthesis and Stereospecific S_N2 Reaction of <i>S</i>-2-Chloro Propionic Acid with Phenoxides
  作者：James A. Aikins、Michael Haurez、John R. Rizzo、Jean-Pierre Van Hoeck、Willy Brione、Jean-Paul Kestemont、Christophe Stevens、Xavier Lemair、Gregory A. Stephenson、Eric Marlot、Mindy Forst、Ioannis N. Houpis

  DOI：10.1021/jo050268e

  日期：2005.6.1

  The stereospecific synthesis of the PPAR alpha/gamma agonist I was accomplished via ethylation of the optically pure tribydroxy derivative 6, itself derived via an enzymatic resolution. The ethylation can be accomplished without epimerization only under strict control of the reaction conditions and the choice of base (sodium tert-amylate), temperature (-30 degrees C), order of addition, and solvent (DMF). The key diastereospecific S(N)2 reaction of the phenol 4 with S-2-chloropropionic acid is best achieved via the sodium phenoxide of 4 derived from Na-0 as the reagent of choice. The structure elucidation and key purification protocols to achieve pharmaceutical purity will also be described.