(4S)-4-苄基-3-(苯基乙酰基)-1,3-恶唑烷-2-酮 | 245323-38-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (4S)-4-苄基-3-(苯基乙酰基)-1,3-恶唑烷-2-酮
• 中文别名: (S)-4-叔丁氧基-4-氧代-2-苯基丁酸
• 英文名称: (S)-4-(tert-butoxy)-4-oxo-2-phenylbutanoic acid
• 英文别名: (2S)-4-[(2-methylpropan-2-yl)oxy]-4-oxo-2-phenylbutanoic acid
• CAS: 245323-38-0
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: ICZBQHPMSPTRJO-NSHDSACASA-N

物化性质

• 熔点：
  76.0-78.5 °C
• 沸点：
  369.7±30.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (4S)-4-苄基-3-(苯基乙酰基)-1,3-恶唑烷-2-酮 在 二甲基硫 、 二苯基磷酸 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 、 三氟乙酸 为溶剂， 反应 9.5h， 生成 (3S)-3-{[(苄氧基)羰基]氨基}-3-苯丙酸
  参考文献：
  名称：

  A General Method for the Synthesis of Enantiomerically Pure β-Substituted, β-Amino Acids through α-Substituted Succinic Acid Derivatives

  摘要：

  A general procedure for the synthesis of enantiopure beta-substituted, beta-amino acids is presented. Alkylation of the sodium enolates derived from chiral N-acyloxazolidinone imides 2 (R = Me, i-Pr, t-Bu, Ph, Bn) with tert-butyl bromoacetate afforded the 2-substituted succinate derivatives 3 in good yields (82-89%) and with high selectivity (greater than or equal to 93:7). Following hydrolysis, Curtius rearrangement of the resulting carboxylic acid provided the enantiopure benzyloxycarbonyl (Cbz)-protected beta-amino esters 6 in good yields (74-79%).

  DOI：

  10.1021/jo990756k
• 作为产物：
  描述：

  (S)-4-benzyl-3-phenylacetyl-2-oxazolidinone 在 lithium hydroxide 、 双氧水 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.5h， 生成 (4S)-4-苄基-3-(苯基乙酰基)-1,3-恶唑烷-2-酮
  参考文献：
  名称：

  A General Method for the Synthesis of Enantiomerically Pure β-Substituted, β-Amino Acids through α-Substituted Succinic Acid Derivatives

  摘要：

  A general procedure for the synthesis of enantiopure beta-substituted, beta-amino acids is presented. Alkylation of the sodium enolates derived from chiral N-acyloxazolidinone imides 2 (R = Me, i-Pr, t-Bu, Ph, Bn) with tert-butyl bromoacetate afforded the 2-substituted succinate derivatives 3 in good yields (82-89%) and with high selectivity (greater than or equal to 93:7). Following hydrolysis, Curtius rearrangement of the resulting carboxylic acid provided the enantiopure benzyloxycarbonyl (Cbz)-protected beta-amino esters 6 in good yields (74-79%).

  DOI：

  10.1021/jo990756k

文献信息

• COMPOUNDS, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN TREATING METABOLIC DISORDERS
  申请人：Hoveyda Hamid

  公开号：US20110230477A1

  公开（公告）日：2011-09-22

  The present invention is directed to novel compounds of formula (I) and their use in treating metabolic diseases.

  本发明涉及式（I）的新化合物及其在治疗代谢性疾病方面的应用。
• [EN] ALPHA V BETA 6 AND ALPHA V BETA 1 INTEGRIN INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE L'INTÉGRINE ALPHA V BÊTA 6 ET ALPHA V BÊTA 1 ET LEURS UTILISATIONS
  申请人：DICE MOLECULES SV INC

  公开号：WO2022192545A1

  公开（公告）日：2022-09-15

  Provided herein are alpha V beta 6 and alpha V beta 1 integrin inhibitors, methods of making such alpha V beta 6 and alpha V beta 1 integrin inhibitors, pharmaceutical compositions of alpha V beta 6 and alpha V beta 1 integrin inhibitors, and methods of treating and/or preventing various medical disorders in a subject by administering to the subject in need thereof alpha V beta 6 and alpha V beta 1 integrin inhibitors.

  本文提供了αVβ6和αVβ1整合素抑制剂，制备这种αVβ6和αVβ1整合素抑制剂的方法，αVβ6和αVβ1整合素抑制剂的药物组合物，以及通过向需要此类抑制剂的受试者投与αVβ6和αVβ1整合素抑制剂来治疗和/或预防各种医学疾病的方法。
• Discovery of the first potent and selective αvβ5 integrin inhibitor based on an amide-containing core
  作者：Rhys A. Lippa、John Barrett、Sandeep Pal、James E. Rowedder、John A. Murphy、Tim N. Barrett

  DOI：10.1016/j.ejmech.2020.112719

  日期：2020.12

  Integrins α_vβ₅ and α_vβ₃ are closely related, proangiogenic members of the wider RGD-binding integrin family. Due to their high sequence homology, the development of α_vβ₅-selective compounds has remained elusive to synthetic and medicinal chemists. Herein, we describe a survey of SAR around a series of amide-containing 3-aryl-succinamic acid-based RGD mimetics. This resulted in the discovery of α,α,α-trifluorotolyl 12 which exhibits 800 × selectivity for α_vβ₅versus α_vβ₃ with a pyrrolidine amide linker that confers selectivity for α_vβ₅ by positioning a key aryl ring in the SDL of α_vβ₅ with good complementarity; binding in this mode is disfavoured in α_vβ₃ due to clashes with key residues in the β₃-subunit. Compound 12 exhibits selective inhibition by a cell adhesion assay, high passive permeability and solubility which enables potential use of this inhibitor as an α_vβ₅-selective in vitro tool compound.
• Preparation of Chiral 3-Arylpyrrolidines via the Enantioselective 1,4-Addition of Arylboronic Acids to Fumaric Esters Catalyzed by Rh(I)/Chiral Diene Complexes
  作者：Yu-Chiang, Chung、Damodar Janmanchi、Hsyueh-Liang Wu

  DOI：10.1021/ol300980k

  日期：2012.6.1

  A highly efficient rhodium-catalyzed protocol for the preparation of 2-arylsuccinic esters and 3-arylpyrrolidines of high optical purity has been achieved. In the presence of 1 mol % of a chiral diene/Rh(I) catalyst, asymmetric addition of various arylboronic acids to di-fert-butyl fumarate (3c) provides the corresponding adducts in up to 99% yield and 94 -> 99.5% ee. Excellent enantioselectivities were also observed in the regio- and enantioselective conjugate addition of phenylboronic acid (4a) to compound 3e.
• [EN] COMPOUNDS, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN TREATING METABOLIC DISORDERS<br/>[FR] COMPOSÉS, COMPOSITION PHARMACEUTIQUE ET MÉTHODES POUR APPLICATION AU TRAITEMENT DE TROUBLES MÉTABOLIQUES
  申请人：EUROSCREEN SA

  公开号：WO2010066682A4

  公开（公告）日：2010-08-26