S-3-苯氨基丁酸 | 142925-36-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: S-3-苯氨基丁酸
• 中文别名: (S)-3-苯氨基丁酸
• 英文名称: (S)-(+)-N-(3-phenylaminobutyryl)benzoic acid
• 英文别名: (S)-3-(phenylamino)butanoic acid；(S)-phenylamino-butyric acid；(S)-3-Phenylamino-butyric acid；(3S)-3-anilinobutanoic acid
• CAS: 142925-36-8
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: FXGNIWAMJJDYMZ-QMMMGPOBSA-N

物化性质

• 沸点：
  363.9±25.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-3-苯氨基丁酸 在 氯化亚砜 作用下， 反应 2.0h， 生成
  参考文献：
  名称：

  Pd/Cu-catalyzed couplings of β-amino esters with aryl bromides. Synthesis of chiral 1,2,3,4-tetrahydro-4-oxo-2-alkyl-1-quinolines

  摘要：

  A new protocol to prepare chiral 1,2,3,4-tetrahydro-4-oxo-2-alkyl-1-quinolines has been developed. The key steps are Pd/Cu-catalyzed couplings of chiral beta-amino esters and aryl bromides, and intramolecular acylation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00078-0
• 作为产物：
  描述：

  3-(3-anilinobutanoyl)-1,3-oxazolidin-2-one 在 lithium hydroxide 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 18.17h， 生成 S-3-苯氨基丁酸
  参考文献：
  名称：

  Amine-Salt-Controlled, Catalytic Asymmetric Conjugate Addition of Various Amines and Asymmetric Protonation

  摘要：

  The combined use of chiral Pd complex 2 and amine salt enabled completely regulated release of free nucleophilic amine. Under these conditions, an efficient catalytic asymmetric conjugate addition of various amines was achieved to afford beta-amino acid derivatives in high chemical yields with up to 98% ee. Furthermore, a highly enantioselective protonation in 1,4-addition of amine was also developed.

  DOI：

  10.1021/ol0493711

文献信息

• [EN] PGD2 RECEPTOR ANTAGONISTS FOR THE TREATMENT OF INFLAMMATORY DISEASES<br/>[FR] ANTAGONISTES DE RECEPTEUR DE LA PROSTAGLANDINE D2 POUR LE TRAITEMENT DE MALADIES INFLAMMATOIRES
  申请人：MILLENNIUM PHARM INC

  公开号：WO2005100321A1

  公开（公告）日：2005-10-27

  Disclosed herein are compounds represented by Structural Formula: (I) and (I-A). Also disclosed is the use of such compounds for inhibiting the G-protein coupled receptor referred to as chemoattractant receptor-homologous molecule expressed on Th2, or simply 'CRTH2' for the treatment of inflammatory disorders. The variables in Structural Formula (I) and (I-A) are defined herein.

  本文披露了由结构式(I)和(I-A)表示的化合物。还披露了利用这些化合物抑制称为趋化剂受体同源分子表达在Th2上的G蛋白偶联受体，简称为'CRTH2'，用于治疗炎症性疾病。结构式(I)和(I-A)中的变量在此处被定义。
• Palladium-catalyzed coupling reaction of amino acids (esters) with aryl bromides and chlorides
  作者：Fangfang Ma、Xiaomin Xie、Lina Ding、Jinsheng Gao、Zhaoguo Zhang

  DOI：10.1016/j.tet.2011.09.109

  日期：2011.12

  showed high efficiency for the coupling reactions of amino acids and inactive aryl halides to give N-aryl amino acids. Under the catalytic conditions, not only α-amino acids, but also β-, γ-, and δ-amino acids have been coupled with aryl chlorides in moderate to high yields; in the case of optically pure β-amino acids as substrates, the optical purities of the coupling products retained.

  庞大且富电子的MOP型配体和Pd（dba）2组合对氨基酸与非活性芳基卤化物的偶合反应显示出N-芳基氨基酸的高效反应。在催化条件下，不仅α-氨基酸，而且β-，γ-和δ-氨基酸都以中等至高收率与芳基氯偶合。在光学纯的β-氨基酸作为底物的情况下，保留了偶联产物的光学纯度。
• Production method for optically active N-aryl-beta-amino acid compounds
  申请人：Ajinomoto Co., Inc.

  公开号：EP1471050A1

  公开（公告）日：2004-10-27

  In a method suitable for industrial application, an optically active N-aryl-β-amino acid compound is produced by the reaction of an aromatic amine and an optically active sulfonylated β-hydroxycarboxylic acid compound. The latter can be easily derived from a β-keto carboxylic acid compound.

  在适用于工业应用的方法中，通过芳香胺和光学活性磺酰化的β-羟基羧酸化合物的反应，可以生产出光学活性的N-芳基-β-氨基酸化合物。后者可以很容易地从β-酮羧酸化合物中衍生出来。
• PGD2 receptor antagonists for the treatment of inflammatory diseases
  申请人：Ghosh Shomir

  公开号：US20050256158A1

  公开（公告）日：2005-11-17

  Disclosed herein are compounds represented by Structural Formula (I) and (I-A): Also disclosed is the use of such compounds for inhibiting the G-protein coupled receptor referred to as chemoattractant receptor-homologous molecule expressed on Th2, or simply “CRTH2” for the treatment of inflammatory disorders. The variables in Structural Formula (I) and (I-A) are defined herein.

  本文揭示了由结构式（I）和（I-A）表示的化合物：还披露了利用这些化合物抑制称为Th2表达的G蛋白偶联受体的化学引诱受体同源分子，简称“CRTH2”，用于治疗炎症性疾病。结构式（I）和（I-A）中的变量在此处被定义。
• Asymmetric Synthesis ofβ-Amino Acid and Amide Derivatives by Catalytic Conjugate Addition of Aromatic Amines toN-Alkenoylcarbamates
  作者：Kelin Li、Xiaohui Cheng、King Kuok (Mimi) Hii

  DOI：10.1002/ejoc.200300740

  日期：2004.3

  We report a highly active palladium catalyst for the enantioselective conjugate addition of primary aromatic amines to N-alkenoylcarbamates, furnishing β-amino N-Boc-amides in extremely high yields (>99 %) and unprecedented optical purity (>99 % ee) with just 2 mol % catalyst loading. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  我们报告了一种高活性钯催化剂，用于伯芳香胺与 N-烯酰基氨基甲酸酯的对映选择性共轭加成，以极高的产率 (>99%) 和前所未有的光学纯度 (>99%ee) 提供 β-氨基 N-Boc-酰胺仅 2 mol% 的催化剂负载量。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)