(S)-2-(2-hydroxybenzylamino)-3-phenylpropanoic acid | 23847-75-8

• 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
• 英文名称: (S)-2-(2-hydroxybenzylamino)-3-phenylpropanoic acid
• 英文别名: Nα-salicyl-L-phenylalanine；(2S)-2-[(2-hydroxyphenyl)methylazaniumyl]-3-phenylpropanoate
• CAS: 23847-75-8
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: SEFJOAZEIDRHSW-AWEZNQCLSA-N

物化性质

• 沸点：
  464.7±40.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  iron(III) ammonium sulfate dodecahydrate 、 (S)-2-(2-hydroxybenzylamino)-3-phenylpropanoic acid 以 水 为溶剂， 生成
  参考文献：
  名称：

  Thermodynamic stabilities and formation mechanisms of iron(III) complexes with Nα-carboxymethyl-Nα-salicyl-l-phenylalanine and Nα-salicyl-l-phenylalanine: Enhanced thermodynamic stability by additional methylcarboxylate group

  摘要：

  The thermodynamic stability and the formation reaction mechanism have been investigated for the iron(III) complexes with a new tetradentate ligand, N-alpha-carboxymethyl-N-alpha-salicyl-L-phenylalanine (1, H(3)cslpa) and the related N-alpha-salicyl-L-phenylalanine (2, H(2)slpa). The mono(ligand)iron(III) complex of 1 formed under both conditions for the metal ion concentration (C-M) being in large excess over the ligand 1 (C-L) and vice versa, while 2 formed a bis(ligand)iron(III) complex in consecutive stages under the conditions C-L >> C-M. The stability constant of the mono (ligand)iron(III) complex of 1 (log beta(11) =21.61 +/- 0.10; beta(11) = [Fe(cslpa)]/[Fe3+][cslpa(3-)]) was larger than the constant of the complex of 2 (log beta(11) = 17.71 +/- 0.09; beta(11) = [Fe(slpa)(+)]/[Fe3+] [slpa(2-)]), which was mainly caused by the chelate effect of an additional methylcarboxylate group. The complexes of 1 and 2 were formed through the composite pathways of Fe3++H(2)L(-(or 0)) (k(32)) and FeOH2++H(3)L(0(or +)) (k(23)) and another single pathway of FeOH2++H(2)L(-(or 0)) (k(22)) [L(3-(or 2-)) = cslpa(3-) (or slpa(2-))]. The rate constants of each pathway for 1 and 2 are the same in magnitude as the corresponding constants of iron(III)-N-alpha-pyridoxyl-L-aspartic acid (4, H(3)plas) and-N-alpha-salicyl-L-alanine systems, respectively. This good agreement in the rate constants suggests a mechanism that the complexes of 1 and 2 form through the slow coordination of the phenolate oxygen followed by the rapid donations of other coordinating atoms.

  DOI：

  10.1016/s0277-5387(00)88146-2
• 作为产物：
  描述：

  L-苯丙氨酸 在 氢氧化钾 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (S)-2-(2-hydroxybenzylamino)-3-phenylpropanoic acid
  参考文献：
  名称：

  Chantegrel, Bernard; Deshayes, Christian; Faure, Rene, Heterocycles, 1993, vol. 36, # 12, p. 2811 - 2818

  摘要：

  DOI：

文献信息

• A Highly Sensitive Luminescent Dye@MOF Composite for Probing Different Volatile Organic Compounds
  作者：Jun-Ping Zheng、Sha Ou、Min Zhao、Chuan-De Wu

  DOI：10.1002/cplu.201600057

  日期：2016.8

  The probing of volatile organic compounds (VOCs) is critical and challenging in biotechnology and environmental monitoring. Incorporation of luminescent moieties into metal-organic frameworks (MOFs) has produced many unique luminescent sensors for probing different VOCs. The emissions of most MOF sensors are based mainly on the single transitions of luminescent moieties, so the luminescence readouts

  在生物技术和环境监测中，挥发性有机化合物（VOC）的探测至关重要且具有挑战性。将发光部分并入金属有机骨架（MOF）中产生了许多独特的发光传感器，用于探测不同的VOC。大多数MOF传感器的发射主要基于发光部分的单个跃迁，因此发光读数仅对某些特殊的VOC占主导地位。我们使用天然氨基酸衍生物作为发光部分，以生成层状配位聚合物，并进一步将发光染料分子嵌入晶体基质中，以产生发光染料@MOF传感器。通过调节从有机配体到染料部分的能量转移效率，复合传感器在解码具有明显不同荧光发射的VOC时表现出出色的灵敏度。复合发光传感器是经过自我校准的，并且比其他更广泛探索的发光传感器更加稳定和即时。
• Amino acid derivatives and compositions containing the same for inhibiting active-oxygen
  申请人：Ajinomoto Co., Inc.

  公开号：EP0869115A2

  公开（公告）日：1998-10-07

  A novel active oxygen-resisting agent is provided which has an excellent active oxygen resistance and which exhibits a good solubility in an oil solvent. The active oxygen-resisting agent contains as an active ingredient an amino acid derivative represented by the following formula (I) or its salt wherein Ar represents a 2-hydroxyphenyl group or a pyridyl group (one or more of hydrogen atoms bound to the aromatic rings of these groups may be substituted independently with a halogen atom, an alkyl group having from 1 to 6 carbon atoms, a hydroxyl group, a hydroxyalkyl group having from 1 to 6 carbon atoms, a nitro group, an alkoxyl group having from 1 to 6 carbon atoms or a carboxyl group), R1 represents a side chain of an animo acid, X represents -O- or -NH-, R2 represents an alkyl group having from 8 to 22 carbon atoms, and n represents 0 or 1.

  本发明提供了一种新型活性抗氧剂，它具有极佳的活性抗氧性，并且在油溶剂中具有良好的溶解性。 该活性抗氧剂的活性成分是由下式（I）或其盐代表的氨基酸衍生物 其中 Ar 代表 2-羟基苯基或吡啶基（与这些基团的芳香环结合的一个或多个氢原子可独立地被卤素原子、1-6 个碳原子的烷基、羟基、1-6 个碳原子的羟烷基、硝基、1-6 个碳原子的烷氧基或羧基取代）、 R1 代表亚胺酸的侧链、 X 代表-O-或-NH-、 R2 代表具有 8 至 22 个碳原子的烷基，以及 n 代表 0 或 1。
• X-ray analysis and structural characterization of 2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononenones
  作者：Hiram I Beltrán、Luis S Zamudio-Rivera、Teresa Mancilla、Rosa Santillan、Norberto Farfán

  DOI：10.1016/s0022-328x(02)01418-3

  日期：2002.9

  Nine new monomeric boronates of the type 2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononen-4-ones (3a-3i) were prepared from N-(2-hydroxybenzyl)-alpha-aminoacids 1a-1i and phenylboronic acid 2 using 20:1 benzene-DMSO mixtures. The compounds were characterized by H-1-, C-13-, B-11-, N-15- and 2D-NMR (HETCOR, NOESY and COLOC) experiments, FT infrared, mass spectra and elemental analysis. Suitable monocrystals of cis-2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononen-4-one (3a), (2S,5S,6R)-2-phenyl-6-aza- 1,3-dioxa-5-sec butyl-2-borabenzocyclononen-4-one (3c) and 2,5-diphenyl-6-aza-1,3-dioxa-2-borabenzocyclononen-4-one (3h) were obtained and their structures are discussed. The X-ray structures, as well as the NMR data established that the configurations at the nitrogen and boron atoms are 'R' and 'S', respectively and the transannular fusion is cis. A semi-empirical (SAMI) study allowed calculation of the energy for all possible stereoisomers, showing that the stabilization increases as the THC (TetraHedral Character of the boron atom) increases and also as the N --> B bond distance decreases, in agreement with the experimental results. (C) 2002 Elsevier Science B.V. All rights reserved.
• Amino acid derivatives as anti-inflammatory agents
  申请人：Ajinomoto Co., Inc.

  公开号：EP0955046B1

  公开（公告）日：2005-06-22
• Chantegrel, Bernard; Deshayes, Christian; Faure, Rene, Heterocycles, 1993, vol. 36, # 12, p. 2811 - 2818
  作者：Chantegrel, Bernard、Deshayes, Christian、Faure, Rene

  DOI：——

  日期：——