3-(4-苄氧基苯基)-2-羟基丙酸乙酯 | 267228-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-(4-苄氧基苯基)-2-羟基丙酸乙酯
• 英文名称: 3-(4-benzyloxyphenyl)-2-hydroxypropionic acid ethyl ester
• 英文别名: ethyl (2S)-3-[4-(benzyloxy)phenyl]-2-hydroxypropanoate；S(-)-ethyl 2-hydroxy-3-(4-benzyloxyphenyl)propionate；S(-)-ethyl-2-hydroxy-3-(4-benzyloxyphenyl) propanoate；(S)-3-(4-benzyloxy-phenyl)-2-hydroxy-propionic acid ethyl ester；ethyl (2S)-2-hydroxy-3-(4-phenylmethoxyphenyl)propanoate
• CAS: 267228-40-0
• 化学式: C₁₈H₂₀O₄
• 分子量: 300.354
• InChiKey: PDLNMIOGVVWRJI-KRWDZBQOSA-N

物化性质

• 沸点：
  450.1±35.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 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-苄氧基苯基)-2-羟基丙酸乙酯 在 咪唑 、 三乙基硅烷 、 bismuth(III) bromide 、 乙醛 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 18.0h， 生成 (S)-ethyl 3-(4-(benzyloxy)phenyl)-2-ethoxypropanoate
  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
• 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-苄氧基苯基)-2-羟基丙酸乙酯
  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

• Process for the preparation of new antidiabetic agents
  申请人：Dr. Reddy's Laboratories Ltd.

  公开号：US06531596B1

  公开（公告）日：2003-03-11

  The present invention relates to an improved process for the preparation of novel antidiabetic compounds having formula (1) where R1 represents hydrogen or lower alkyl group and X represents hydrogen or halogen atom.

  本发明涉及一种改进的制备新型抗糖尿病化合物的方法，其化学式为（1），其中R1代表氢或较低的烷基基团，X代表氢或卤原子。
• 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。
• Modulators of peroxisome proliferator activated receptors
  申请人：Brooks Alisa Dawn

  公开号：US20050020684A1

  公开（公告）日：2005-01-27

  Disclosed is a compound represented by Structural Formula (I): Ar is a substituted or unsubstituted aromatic group. Q is a covalent bond, —CH 2 — or —CH 2 CH 2 —; W is a substituted or unsubstituted alkylene or a substituted or unsubstituted heteroalkylene linking group from two to ten atoms in length, preferably from two to seven atoms in length. Phenyl Ring A is optionally substituted with up to four substituents in addition to R 1 and W, R 2 is (CH 2 ) n —CH(OR 2 )—(CH 2 ) n E, —(CH)═C(OR 2 )—(CH 2 ) n E, —(CH 2 ) n —CH(Y)—(CH 2 ) m E or (CH)═C(Y)(CH 2 ) m E; wherein E is COOR 3 , C 1 -C 3 alkylnitrile, carboxamide, sulfonamide, acylsulfonamide or tetrazole and wherein sulfonamide, acylsulfonamide and tetrazole are optionally substituted with one or more substituents independently selected from: C 1 -C 6 alkyl, haloalkyl and aryl-C o - 4 -alkyl; R 2 is H, an aliphatic group, a substituted aliphatic group, haloalkyl, an aromatic group, a substituted aromatic group, —COR 4 , —COOR 4 , —CONR 5 R 6 , —C(S)R 4 , —C(S)OR 4 or C(S)NR 5 R 6 , R 3 is H, an aliphatic group, a substituted aliphatic group, an aromatic group or a substituted aromatic group. Y is O—, CH 2 —, CH 2 CH 2 — or CH═CH— and is bonded to a carbon atom in Phenyl Ring A that is ortho to R 1 . R 4 -R 6 are independently H, an aliphatic group, a substituted aliphatic group, an aromatic group or a substituted aromatic group. n and m are independently 0, 1 or 2.

  本发明公开了一种由结构式（I）表示的化合物：其中Ar是取代或未取代的芳香基团。Q是共价键，-CH2-或-CH2CH2-; W是取代或未取代的烷基或取代或未取代的异烷基连接基，长度为两到十个原子，优选长度为两到七个原子。苯环A可选地与R1和W以外的最多四个取代基取代，R2是（CH2）n-CH（OR2）-（CH2）nE，-（CH）=C（OR2）-（CH2）nE，-（CH2）n-CH（Y）-（CH2）mE或（CH）=C（Y）（CH2）mE;其中E是COOR3，C1-C3烷基腈，羧酰胺，磺酰胺，酰基磺酰胺或四唑，磺酰胺，酰基磺酰胺和四唑可选地与一个或多个取代基取代，独立地选自：C1-C6烷基，卤代烷基和芳基-Co-4-烷基; R2是H，脂肪基，取代脂肪基，卤代烷基，芳基，取代芳基，-COR4，-COOR4，-CONR5R6，-C（S）R4，-C（S）OR4或C（S）NR5R6，R3是H，脂肪基，取代脂肪基，芳基或取代芳基。Y是O-，CH2-，CH2CH2-或CH═CH-，并与Phenyl环A中与R1相邻的碳原子键合。R4-R6独立地是H，脂肪基，取代脂肪基，芳基或取代芳基。n和m独立地为0、1或2。
• [EN] PPAR-SPARING COMPOUNDS FOR THE TREATMENT OF METABOLIC DISEASES<br/>[FR] COMPOSÉS ÉPARGNANT LES PPAR POUR LE TRAITEMENT DE MALADIES MÉTABOLIQUES
  申请人：METABOLIC SOLUTIONS DEV CO LLC

  公开号：WO2015013187A8

  公开（公告）日：2015-08-20
• [EN] PROCESS FOR PREPARING 3-ARYL-2-HYDROXY PROPANOIC ACID DERIVATIVES WITHOUT RESOLUTION<br/>[FR] PROCEDE DE PREPARATION DE DERIVES D'ACIDE 3-ARYL-2-ALCOXY PROPANOIQUE SANS ETAPE DE RESOLUTION
  申请人：CADILA HEALTHCARE LTD

  公开号：WO2005019152A3

  公开（公告）日：2005-08-11