[(2-hydroxynaphthalen-1-ylmethylene)amino]acetic acid | 55260-17-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(2-hydroxynaphthalen-1-ylmethylene)amino]acetic acid
• 英文别名: N-(2-hydroxy-1-naphthylmethylidene)-glycine；2-hydroxy-1-naphthaldehyde glycine；glycine-2-hydroxy-1-naphthaldehyde；N-2-hydroxynaphthalideneglycine；2-hydroxy-1-naphthaldehyde-glycine；H2napgly；2-[(2-Hydroxynaphthalen-1-yl)methylideneamino]acetic acid
• CAS: 55260-17-8
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: COWXMFPLOIXJFA-UHFFFAOYSA-N

物化性质

• 沸点：
  459.8±30.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  二苯基二氯化锡 、 [(2-hydroxynaphthalen-1-ylmethylene)amino]acetic acid 在 Et₃N 作用下， 以 乙醇 为溶剂， 以75%的产率得到
  参考文献：
  名称：

  二苯基(2-氧化萘基甲基-亚氨基乙酰基)锡(IV)的合成、分子和晶体结构

  摘要：

  制备了新的二有机锡配合物 ((C6HS),Sn(OC,,H6CH=NCH2COO))，并通过 1H NMR、IR、元素分析和单晶 X 射线衍射研究对其进行了表征。晶体为单斜晶系，空间群 P2,la，a = 16.9167(9) A, b = 19.1276(16) A, c = 26.538(2) A, P = 100.534(6)", V= 8442.5(11) A3 , Z= 16, and DCaIc = 1.574 Mg m-3. 6524次显着反射的最终差异因子为R, = 0.030, Rw = 0.02 1 锡原子具有扭曲的三角双锥配位，没有短的分子间接触。 2.12 A 和 2.09 A 的两个轴向 Sn-0 键和 2.14 8 的赤道 Sn-N 键是相关配合物中最短的。

  DOI：

  10.1139/v96-233
• 作为产物：
  描述：

  聚甘氨酸 、 2-羟基-1-萘甲醛 以 甲醇 为溶剂， 反应 0.33h， 生成 [(2-hydroxynaphthalen-1-ylmethylene)amino]acetic acid
  参考文献：
  名称：

  Liquid Chromatographic Determination of Neurotransmitter Serotonin from Human Cerebrospinal Fluid Using 2-Hydroxynaphtaldehyde as Derivatizing Reagent

  摘要：

  以2-羟基萘醛为试剂，通过分光光度法和反相高效液相色谱法分离和测定了甘氨酸、赖氨酸、章鱼胺、血清素和酪胺。在水-甲醇溶液中考察了衍生物的pH值、衍生试剂浓度和加热时间对光谱的影响。衍生物的摩尔吸光系数为2.8×10³至7.7×10³L mol⁻¹ cm⁻¹。在λmax420 nm处观测到的分光光度校准曲线范围为1.0-20.0 μg mL⁻¹。2-羟基萘醛衍生物在Kromasil 100 C-18 10 μm（25 cm × 0.46 cm内径）柱上易于洗脱和分离。洗脱使用甲醇：水：乙腈和醋酸盐缓冲液（0.1 M，pH 6）（47:25:18:10 v/v/v/v），流速为1 mL min⁻¹，紫外检测波长为240 nm。检测了多种氨基酸和药物添加剂，均未干扰测定。该方法成功应用于从药物制剂中测定赖氨酸，以及从人体脑脊液中测定血清素和甘氨酸。进一步用标准添加法支持分析。从药物制剂中回收赖氨酸的回收率为97.46%，相对标准偏差（RSD）为2.8%。从人体脑脊液中测定的甘氨酸和血清素浓度分别为8.13-16.118 μmol L⁻¹和3.92-7.44 nmol L⁻¹，RSD分别为1.6-3.3%和1.4-3.6%。

  DOI：

  10.14233/ajchem.2013.15023

文献信息

• Experimental and Theoretical Investigations of Spectral, Tautomerism and Acid-Base Properties of Schiff Bases Derived from Some Amino Acids
  作者：Y.H. Ebead、H.M.A. Salman、M.A. Abdellah

  DOI：10.5012/bkcs.2010.31.04.850

  日期：2010.4.20

  The electronic absorption spectra of five Schiff bases derived from 2-hydroxy-1-naphthaldehyde with glycine, alanine, leucine, valine and phenylalanine have been measured in various solvents. The observed bands were assigned to the proper electronic transitions and compared with the predicted transitions at the semiempirical level of theory. The calculated equilibrium constants are in agreement with

  已在各种溶剂中测量了从 2-羟基-1-萘醛与甘氨酸、丙氨酸、亮氨酸、缬氨酸和苯丙氨酸衍生的五种席夫碱的电子吸收光谱。观察到的带被分配给适当的电子跃迁，并在半经验理论水平上与预测的跃迁进行比较。计算的平衡常数与实验结果一致，预测所有研究的化合物主要或完全存在于酮亚胺互变异构中。另一方面，已经建立了 ν (cm -1 )（每种化合物的主频率）与众所周知的溶剂参数 ET (30), er, π* 之间的相关性。此外，酸解离常数 pKa 是通过使用三种不同的分光光度法测定的。
• Rational design of two bpy-bridged 3D and 2D CoII open frameworks with similar amino-acid-based Schiff bases
  作者：Zong-Ze Li、Lin Du、Jie Zhou、Ming-Rong Zhu、Fen-Hua Qian、Jing Liu、Peng Chen、Qi-Hua Zhao

  DOI：10.1039/c2dt31670f

  日期：——

  Two novel bpy-bridged CoII Schiff base complexes have been synthesized by the hydro(solvo)thermal reactions of corresponding amino-acid-based Schiff bases, bpy and Co(NO3)2·6H2O. The following formulae identify the two complexes: [Co(napala)(bpy)0.5]·H2O}n (1) and [Co(napgly)(bpy)0.5]n (2) [H2napala = N-(2-hydroxy-1-naphthylmethylidene)-D/L-alanine, H2napgly = N-(2-hydroxy-1-naphthylmethylidene)-glycine and bpy = 4,4′-bipyridine]. These two compounds have been characterized using single-crystal X-ray diffraction, infrared, powder X-ray diffraction, thermogravimetric analysis, optical spectra analysis, and magnetic measurement. Complex 1 features an unprecedented threefold interpenetrated diamond network based on the fan-shaped CoII4(μ2-napala)4 molecular square node and bpy linker, which represents the first example of 3D framework among the amino-acid-based Schiff base complexes with salicylaldehyde or its derivatives. In 2, adjacent CoII ions are bridged by μ2-napgly2− to form left- and right-handed [CoII(μ2-napgly)]n helical chains. These two types of helical chains are sustained alternately by a symmetrical bpy co-ligand into a 2D grid-based layer. The solid-state fluorescence of complexes 1 and 2 are quenched almost completely compared with free mixed-ligands at room temperature. Moreover, magnetic studies show the dominant antiferromagnetic coupling between the CoII centers mediated by the syn–anti-COO−-bridges in both complexes.

  通过相应的氨基酸基希夫碱、bpy和Co(NO3)2·6H2O的溶剂热反应，合成了两种新颖的bpy桥联CoII希夫碱配合物。以下公式标识了这两个配合物： [Co(napala)(bpy)0.5]·H2O}n (1) 和 [Co(napgly)(bpy)0.5]n (2) [H2napala = N-(2-羟基-1-萘基亚甲基)-D/L-丙氨酸，H2napgly = N-(2-羟基-1-萘基亚甲基)-甘氨酸 和 bpy = 4,4′-联吡啶]。这两个化合物通过单晶X射线衍射、红外光谱、粉末X射线衍射、热重分析、光学光谱分析和磁性测量进行了表征。配合物1具有基于扇形CoII4(μ2-napala)4分子方块节点和bpy连接剂的前所未有的三重互穿金刚石网络，这是氨基酸基希夫碱配合物中首个三维框架结构，其中含有水杨醛或其衍生物。在2中，相邻的CoII离子通过μ2-napgly2−桥联形成左旋和右旋的[CoII(μ2-napgly)]n螺旋链。这两种类型的螺旋链由对称的bpy配体交替地维持成一个基于2D网格的层。配合物1和2的固态荧光在室温下几乎完全被淬灭，相比于自由混合配体。此外，磁性研究表明，在两个配合物中，通过syn–anti-COO−桥联，CoII中心之间的反铁磁耦合起主导作用。
• Synthesis, Characterization and Electrochemical Studies on the Interaction Mechanism of Ternary Cu(II) Complex with DNA
  作者：Shuangyu Bi、Nan Zhang、Jian Zuo、Pengfei Zhang、Zhen Zhang、Feng Guo、Yuhua Fan

  DOI：10.14233/ajchem.2013.13893

  日期：——

  A new ternary complex of Cu(II) with Schiff base 2-hydroxy-1-naphthaldehyde-glycine (KHL) and 8-hydroxyquinoline (OHQ) was synthesized and characterized by elemental analysis, IR, TG-DTG and molar conductance. The composition of the complex was confirmed to be [Cu(L)(OHQ)]·2H2O. The fundamental electrochemical characteristics of the Cu(II) complex have been studied and the interaction of the copper complex and DNA was also studied by cyclic voltammetry and fluorescence spectra. The results of the cyclic voltammetry showed that the Cu(II) complex had an oxidation peak with the oxidation potential at -0.394 V. After the DNA was added, the peak current declined with the peak potential shifting positively. This suggested that the complex combined with DNA in the form of intercalative binding, which was also proved by the fluorescence analysis. The binding ratio between the Cu(II) ternary complex and DNA was calculated to be 1:1 and the binding constant was 4.6 × 102 L mol-1.

  通过元素分析、红外光谱、TG-DTG 和摩尔电导，合成了一种新的 Cu(II) 与希夫碱 2-hydroxy-1-naphthaldehyde-glycine (KHL) 和 8-hydroxyquinoline (OHQ) 的三元络合物。经确认，该复合物的组成为 [Cu(L)(OHQ)]-2H2O。研究了 Cu(II) 复合物的基本电化学特性，并通过循环伏安法和荧光光谱研究了铜复合物与 DNA 的相互作用。循环伏安法的结果表明，铜（II）配合物有一个氧化峰，氧化电位为-0.394 V。加入 DNA 后，峰值电流下降，峰值电位正移。这表明配合物与 DNA 以插层结合的形式结合，荧光分析也证明了这一点。经计算，Cu(II) 三元复合物与 DNA 的结合率为 1:1，结合常数为 4.6 × 102 L mol-1。
• Two 2D grid-based Co(II) amino acid Schiff base complexes with left- and right-handed helical chains: Structures and magnetism
  作者：Zong-Ze Li、Lin Du、Xue-Zhong Zhang、Zhu-Li Li、Lin Li、Jing Yang、Qi-Hua Zhao

  DOI：10.1016/j.inoche.2014.03.034

  日期：2014.7

  Two layered Co(II) amino acid Schiff base complexes, [Co(napala)(tbpe)(0.5)] (1) and [Co(napgly)(tbpe)(0.5)](n) (2) [H(2)napala = N-(2-hydroxy-1-naphthylmethylidene)-D/L-alanine, H(2)napgly = N-(2-hydroxy-1-naphthylmethylidene)-glycine and tbpe = trans-1,2-bis(4-pyridyl)ethylenel, have been synthesized by solvothermal methods and characterized using single-crystal X-ray diffraction. The bridging of Schiff base ligands napala(2-) or napgly(2-) with Co(II) forms one-dimensional (1D) left- and right-handed helical chains which are further pillared by tbpe to build a two-dimensional (2D) grid-based hcb-type framework. Moreover, both complexes show high thermal stability and exhibit antiferromagnetic coupling between the Co(II) centers mediated by the syn-anti-COO--bridges. (C) 2014 Elsevier B.V. All rights reserved.
• Singh, H. L.; Sharma, M.; Gupta, M. K., Bulletin of the Polish Academy of Sciences: Chemistry, 1999, vol. 47, # 2, p. 103 - 110
  作者：Singh, H. L.、Sharma, M.、Gupta, M. K.、Varshney, A. K.

  DOI：——

  日期：——