salicylalanine | 34208-97-4

• 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: salicylalanine
• 英文别名: L-Alanine, N-[(2-hydroxyphenyl)methylene]-；(2S)-2-[(2-hydroxyphenyl)methylideneamino]propanoic acid
• CAS: 34208-97-4
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: IAXKPCNASAJLRO-ZETCQYMHSA-N

物化性质

• 熔点：
  85.6-86.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  360.2±27.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  69.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  salicylalanine 在 N,N-二甲基丙烯基脲 、 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 反应 5.25h， 生成 tert-butyl 3-[[(3R,10bR)-3-methyl-2,5-dioxo-10bH-[1,3]oxazolo[3,2-c][1,3]benzoxazin-3-yl]methyl]indole-1-carboxylate
  参考文献：
  名称：

  The stereocontrolled synthesis of orthogonally protected (R)-α-methyltryptophan

  摘要：

  An expedient and highly stereocontrolled route to (R)-alpha-methyltryptophan and its orthogonally protected analogs has been developed via a four-step conversion from L-alanine in good overall yields. The stereochemistry of the products is confirmed by X-ray diffraction analysis, NMR spectroscopy and optical rotations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02302-8
• 作为产物：
  描述：

  L-丙氨酸 、 水杨醛 以 甲醇 、 水 为溶剂， 反应 24.0h， 以70%的产率得到salicylalanine
  参考文献：
  名称：

  A New Fluorescent “Off-On” Sensor for Al3+ Derived from L-alanine and Salicylaldehyde

  摘要：

  L-丙氨酸和水杨醛的缩合物被合成并进行了表征，发现其是Al3+离子的选择性荧光“开启”传感器，检测限为10−6 M。该传感器不受金属离子（Na+、K+、Ca2+、Mn2+、Co2+、Ni2+、Cu2+、Pb2+、Cd2+、Hg2+和Fe3+）的干扰。荧光和紫外/可见光谱数据显示传感器与Al3+离子之间存在1:1相互作用，结合常数为104.5。DFT和TDDFT计算证实了传感器和传感器-Al3+复合物的结构。

  DOI：

  10.1007/s10895-015-1647-5

文献信息

• Assessing the Effect of Ligand Proximity on Chiroptical and Other Properties in Cobalt(III) Model, Tyrosine-Like Complexes
  作者：František Jursík、Ronald D. Archer

  DOI：10.1135/cccc19952097

  日期：——

  A series of new cobalt(III) octahedral complexes of the general formula Na[Co(ohb-aa)₂] (ohb-aa = N-(o-hydroxybenzyl)amino acid anion); amino acid = glycine, (S)-α-alanine, α-aminoisobutyric acid, (S)-valine, (S)-norvaline and (S)-leucine) were prepared by the charcoal catalyzed reaction of the appropriate ligand with [Co(NH₃)₆]³⁺ in alkaline aqueous solution. Complexes obtained have, regardless of the amino acid used, the same facial all-trans symmetry (CoN₂O₄ chromophore) with the vicinal effects as the entire source of the optical activity. ¹³C NMR spectra reveal that the leucine derivative has, due to the steric reasons, a different ground state structure. Absorption maxima reflect a positive inductive effect from the amino acid side chain carbon atoms. Complexes of the ligands bearing electrophobic alkyl groups exhibit more negative E_1/2 in comparison with the glycine derivative, reduction of which occurs at a more positive potential. Reduction potentials do not correlate with cobalt(III) Lewis acidity modulated by ligands.

  一系列新的钴（III）八面体配合物的通式为Na[Co(ohb-aa)₂]（ohb-aa = N-(o-羟基苯甲基)氨基酸根离子）；氨基酸=甘氨酸，(S)-α-丙氨酸，α-氨基异丁酸，(S)-缬氨酸，(S)-正缬氨酸和( S)-亮氨酸），通过适当配体在碱性水溶液中与[Co(NH₃)₆]³⁺在木炭催化下反应制备。无论使用哪种氨基酸，所得到的配合物具有相同的facial all-trans对称性（CoN₂O₄色团），邻位效应是光学活性的全部来源。¹³C NMR光谱显示，由于立体位阻，亮氨酸衍生物具有不同的基态结构。吸收峰反映了氨基酸侧链碳原子的正电感应效应。具有亲电性烷基基团的配体配合物与甘氨酸衍生物相比，表现出更负的E_1/2，其还原发生在更正的电位。还原电位与由配体调节的钴（III）路易斯酸性不相关。
• Synthesis, protonation constants and biological activity determination of amino acid–salicylaldehyde-derived Schiff bases
  作者：Claudia Fattuoni、Sarah Vascellari、Tiziana Pivetta

  DOI：10.1007/s00726-019-02816-0

  日期：2020.3

  spectroscopic characterization of these compounds. For this reason, six Schiff bases, derived from salicylaldehyde and natural amino acids were fully characterized by nuclear magnetic resonance and infrared spectroscopy, and their aqueous solution equilibria, antiproliferative activity and DNA-binding activity were examined. All experimental conditions were kept constants to achieve comparable information

  Schiff碱代表了一类因在有机化学和配位化学中的重要性而广泛研究的分子。尽管对席夫碱的化学和生物学性质进行了大量研究，但不同的实验条件仍无法进行有用的比较以寻找相关的结构-活性。此外，文献缺乏关于这些化合物的光谱表征的全面数据。因此，通过核磁共振和红外光谱对六种衍生自水杨醛和天然氨基酸的席夫碱进行了充分表征，并对其水溶液平衡，抗增殖活性和DNA结合活性进行了研究。将所有实验条件保持恒定，以获取有关其结构-活性相关性的可比信息和有用见解。合成的化合物在10个分子中显示出DNA结合常数1 – 10 2  M -1范围，取决于氨基酸侧链中存在的取代基，导致对不同的人类肿瘤细胞株没有明显的细胞毒活性，显示出IC50值高于100 µM。
• A non-covalent interaction of Schiff base copper alanine complex with green synthesized reduced graphene oxide for highly selective electrochemical detection of nitrite
  作者：Subramanian Sakthinathan、Subbiramaniyan Kubendhiran、Shen-Ming Chen、Fahad M. A. Al-Hemaid、Wei Cheng Liao、P. Tamizhdurai、S. Sivasanker、M. Ajmal Ali、A. A. Hatamleh

  DOI：10.1039/c6ra20580a

  日期：——

  A novel and selective nitrite sensor based on non-covalent interaction of Schiff base copper complex [Cu(sal-ala)(phen)] with reduced graphene oxide (RGO) was developed by simple eco-friendly approach.

  本研究采用简单环保的方法，基于希夫碱铜络合物[Cu(sal-ala)(phen)]与还原型氧化石墨烯（RGO）的非共价作用，开发了一种新型选择性亚硝酸盐传感器。
• Topochemical Conversion of a Hydrogen-Bonded Three-Dimensional Network into a Covalently Bonded Framework
  作者：John D. Ranford、Jagadese J. Vittal、Daqing Wu

  DOI：10.1002/(sici)1521-3773(19980504)37:8<1114::aid-anie1114>3.0.co;2-e

  日期：1998.5.4

  Thermal dehydration promotes the topochemical conversion of the hydrogen-bonded dimeric complex [Zn(sala)(H2 O)2 }2 ]⋅2 H2 O (H2 (sala)=N-(2-hydroxybenzyl)-L-alanine) to generate covalent [Zn(sala)}n ]. X-ray crystallography reveals that hydrogen bonding plays a key role in this process (see the partial structure on the right).

  热脱水促进氢键联的二聚配合物[Zn（sala）（H 2 O）2 } 2 ]⋅2H 2 O（H 2（sala）= N-（2-羟基苄基）-L-丙氨酸）以生成共价[Zn（sala）} n ]。X射线晶体学分析表明，氢键在该过程中起关键作用（请参见右侧的部分结构）。
• Ability of two novel α-amino acid-based tridentate ligands to complex Fe3+ in solution
  作者：Kirandeep Kaur、Minati Baral

  DOI：10.1007/s11164-014-1689-3

  日期：2015.8

  Two novel α-amino acid-based tridentate ligands, L1 and L2, were synthesized, and characterized by use of spectroscopic methods. Potentiometric and spectrophotometric methods were used to study the pH-dependent protonation behavior of the ligands and their complexation towards Fe(III) in aqueous medium of ionic strength, µ = 0.1 M KCl at 25 ± 1 °C. The stability constants of complex species of the types FeLH3, FeLH2, FeLH, FeL, and FeL2 (L = L1 or L2) were determined, and probable structures of the ferric complexes were proposed on the basis of molecular modeling. The complexing ability of the ligands was compared with that of deferiprone (a drug used for medical treatment of iron intoxication) and transferrin (the main Fe-binding protein in plasma).

  两种新型α-氨基酸三叉配体L1和L2被合成，并通过光谱法进行了表征。在25±1°C、离子强度为µ=0.1M KCl的水介质中，通过电位法和分光光度法研究了配体与Fe(III)的络合反应，以及配体与Fe(III)的pH依赖性质子化行为。确定了FeLH3、FeLH2、FeLH、FeL和FeL2（L=L1或L2）的稳定性常数，并根据分子模型提出了铁络合物的可能结构。将配体的络合能力与去铁酮（一种用于治疗铁中毒的药物）和转铁蛋白（血浆中主要的铁结合蛋白）进行了比较。