1-[(2-hydroxy-ethylimino)-methyl]-naphthalen-2-ol | 1082-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[(2-hydroxy-ethylimino)-methyl]-naphthalen-2-ol
• 英文别名: 2-hydroxy-naphthaldehyde-(1-){2-hydroxy-ethylimine}；1-((2-Hydroxyethyl)iminomethyl)-2-naphthol；1-(2-hydroxyethyliminomethyl)naphthalen-2-ol
• CAS: 1082-25-3
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: PRTPQYWIXUPHAT-UHFFFAOYSA-N

物化性质

• 熔点：
  154 °C
• 沸点：
  419.2±30.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(2-hydroxy-ethylimino)-methyl]-naphthalen-2-ol 、 uranyl 在 amine 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Mehta, R. K.; Gupta, R. K.; Singhi, V. C., Journal fur praktische Chemie (Leipzig 1954), 1973, vol. 315, p. 843 - 849

  摘要：

  DOI：
• 作为产物：
  描述：

  C.I.酸性橙108 、 2-羟基-1-萘甲醛 以 乙醇 为溶剂， 以78%的产率得到1-[(2-hydroxy-ethylimino)-methyl]-naphthalen-2-ol
  参考文献：
  名称：

  复杂的二氧杂钼（VI）化合物与芳香邻羟基醛的醇亚胺。2-羟基亚萘基单乙醇亚胺（H 2 L）和溶剂化物[MoO 2（L）·C 5 H 5 N]的晶体结构

  摘要：

  摘要已经合成了作为2-羟基萘醛和单乙醇胺（H 2 L）的衍生物的席夫碱和二氧钼（VI）[MoO 2（L）·C 5 H 5 N]（I）的内络合物。H 2 L和I的结构已经通过IR光谱和X射线衍射确定。在单核分子I中，Mo原子具有由两个氧配体（Mo = O 1.683（4）和1.697（3）Å），醇的去质子化羟基的两个O原子（Mo–O（ 4）1.919（4）Å）和醛（Mo–O（3）1.962（3）Å）片段，以及三齿双螯合物双电荷配体L 2–的N原子（Mo–N L 2.262（4）Å）和吡啶分子的N原子（Mo–N Py 2.496（4）Å）。Mo-N L和Mo-N Py键由于多重结合的氧代配体的反式影响而显着延长。游离的H 2 L分子以醌型（酮胺）互变异构形式结晶，在配合物I中，它以双去质子化的苯甲酸酯（烯醇-亚胺）形式配位。

  DOI：

  10.1134/s0036023620040166

文献信息

• Structure and Solution Equilibrium of N-Salicylidene-amino-sugars and Amino-alcohols.
  作者：Shigeharu Inouye

  DOI：10.1248/cpb.15.1540

  日期：——

  The structures and solution equilibria of twenty members of N-salicylidene-amino-sugars and -amino-alcohols were examined mainly in methanol, water and solid state. As the modeled compounds were examined simultaneously three members of N-salicylidene-alkylamines and eight members belonged to the o-methoxybenzylidene, 3-methoxysalicylidene, 3, 5-dibromosalicylidene and 2-hydroxynaphthylidene derivatives. From the comparative studies on the electronic, infrared, NMR spectra and equilibrium position, it was shown that the solution equilibrium consisted of the phenolimine and the ketoamine species, the latter being stabilized by the intra- and intermolecular hydrogen bonding involving the alcoholic hydroxyl groups and protic solvents. The acid-base equilibria of the two tautomers in methanol and the ketoamine-ion-pair equilibrium in water were discussed.

  二十种N-水杨醛基氨基糖和氨基醇的结构及溶液平衡主要在甲醇、水和固态下进行了研究。由于所建模的化合物是同时考察的，因此其中包括三种N-水杨醛基烷基胺和八种属于o-甲氧基苯亚甲基、3-甲氧基水杨醛基、3,5-二溴水杨醛基和2-羟基萘亚甲基衍生物。从电子、红外、核磁共振谱及平衡位置的比较研究中显示，溶液平衡由酚亚胺和酮胺物种组成，后者通过涉及醇羟基和质子溶剂的分子内和分子间氢键得以稳定。讨论了甲醇中两个互变异构体的酸碱平衡以及水中酮胺离子对的平衡。
• Mn(IV), Co(II) and Ni(II) complexes of the Schiff bases of 2-hydroxy-naphthaldehyde with amino alcohols: synthesis, characterization and electrochemical study; DFT study and Catecholase activity of Mn(IV) complex
  作者：Shipra Sagar、Arfa Parween、Tarun K. Mandal、William Lewis、Subhendu Naskar

  DOI：10.1080/00958972.2020.1832657

  日期：2020.11.16

  acetonitrile by UV-Vis spectrophotometric technique. The kinetic study revealed that 1 has a moderate catecholase activity (k cat = 812 h−1), whereas 2–4 are inactive. Electronic structure of 1 and 4 has been established by theoretical calculation. Structures of both complexes have been optimized by DFT. Experimental electronic spectra of the complexes have been corroborated by TD-DFT analysis. Graphical Abstract

  摘要 四种新的单核配合物，[MnIV(L1)2] (1)、[CoII(HL1)2] (2)、[NiII(HL1)2] (3) 和 [NiII(HL2)2] (4) , 配体 H2L1 (2-羟基乙基亚氨基) 甲基萘酚) 和 H2L2 (3-羟基丙基亚氨基) 甲基萘酚) 已被合成、表征，并研究了它们的儿茶酚酶活性。单晶 X 射线衍射研究表明，1 在 P43212 空间群中结晶并采用经向八面体几何形状，而具有方形平面几何形状的 4 在 P21/n 空间群中结晶。儿茶酚酶活性已通过紫外-可见分光光度计技术在乙腈中进行了研究。动力学研究表明，1 具有中等儿茶酚酶活性（k cat = 812 h-1），而 2-4 是无活性的。1和4的电子结构已经通过理论计算建立。两种复合物的结构都已通过 DFT 进行了优化。复合物的实验电子光谱已通过 TD-DFT 分析得到证实。图形概要
• Structural characterization of possible intermediates in vanadium-catalysed sulfide oxidation
  作者：Hauke Schmidt、Mandana Bashirpoor、Dieter Rehder

  DOI：10.1039/dt9960003865

  日期：——

  Reaction between 3-methoxysalicylaldehyde and (R,R)-1,2-diaminocyclohexane with VO2+ as a template yielded the racemic Schiff-base complex [VO(L1)][H2L1=N,N′-bis(3-methoxysalicylidene)cyclohexane-1,2-diamine] which is converted into trans-[VCl2(L1)] with SOCl2. The crystal structures of both have been determined. The former is a tetragonal-pyramidal complex, whereas the structure of the latter is best described as an octahedron distorted towards a trigonal prism. The complex [VO(acac)2](acac = acetylacetonate) reacted with HN(CH2CH2OH)2 in the presence of oxygen to yield [VO(acac)PhN(CH2CH2O)2}], the crystal structure of which reveals a co-ordination geometry in-between tetragonal-pyramidal and octahedral (provided by a weak vanadium-to-nitrogen bonding interaction). Aeration of a reaction mixture consisting of [VO(acac)2] and the Schiff base (H2L2) formed between H2NCH2CH2OH and o-hydroxynaphthaldehyde afforded [VO(L2)}2O] having a bent and slightly asymmetric oxo-bridge, and an additional weak bridging interaction between one of the V–O (ethanolate) centres and the second vanadium centre (crystal structure). In solution, the inequivalency of the two vanadium centres is offset. The reactivity of the complexes towards Me2SO and/or PhSMe has been studied by EPR and 51V NMR spectroscopy.

  以 VO2+ 为模板，3-甲氧基水杨醛和 (R,R)-1,2-环己烷二胺反应生成了外消旋席夫碱复合物 [VO(L1)][H2L1=N,N′-双(3-甲氧基水杨醛基)-1,2-环己烷二胺]，该复合物在 SOCl2 的作用下转化为反式 [VCl2(L1)]。这两种物质的晶体结构均已确定。前者是一个四方五面体复合物，而后者的结构最好描述为一个向三棱柱变形的八面体。复合物 [VO(acac)2]（acac = 乙酰丙酮）在有氧气存在的情况下与 HN(CH2CH2OH)2 反应生成 [VO(acac)PhN(CH2CH2O)2}]，其晶体结构显示出一种介于四方金字塔和八面体之间的配位几何结构（由弱的钒-氮键相互作用提供）。将[VO(acac)2]和 H2NCH2CH2OH 与邻羟基萘甲醛之间形成的希夫碱（H2L2）组成的反应混合物通气后，得到了[VO(L2)}2O]，它具有弯曲和轻微不对称的氧桥，而且其中一个 V-O（乙醇酸）中心和第二个钒中心之间还存在着微弱的桥接作用（晶体结构）。在溶液中，两个钒中心的不等价性被抵消。这些复合物对 Me2SO 和/或 PhSMe 的反应性已通过 EPR 和 51V NMR 光谱进行了研究。
• Synthesis, characterization and catalytic properties of dinuclear complexes of copper(II) and nickel(II): Oxidation of cyclohexane, toluene and cyclopentane
  作者：Aradhita Bhattacharjee、Sudipto Dey、Partha Roy

  DOI：10.1016/j.ica.2019.03.005

  日期：2019.5

  investigate spectral transitions. Copper(II) complex shows effective catalytic ability towards oxidation of the saturated hydrocarbons such as cyclohexane, toluene and cyclopentane in the presence of hydrogen peroxide when corresponding alcohols and ketones have been obtained as major products. However, complex 2 has been found to be inactive as catalyst for the oxidation. It is possible that Cu-hydroperoxo

  摘要过渡金属络合物氧化饱和烃非常重要，因为这将产生工业上有价值的有机精细化学品。在此，使用具有相同N，O供体配体的双核铜（II）和双核镍（II）配合物作为使用过氧化氢作为氧化剂氧化环己烷，甲苯和环戊烷的催化剂，以检验其催化活性和自然作用金属中心的催化作用。[Cu2（L1）2（μ2-Cl）Cl]·2.5H2O（1）和[Ni2（L1）2（μ2-N3）2（CH3OH）2]·CH3OH（2）在HL1温和的条件下合成是1-（（2-羟乙基亚氨基）甲基）萘-2-醇。这些配合物已通过元素分析，FT-IR，UV-Vis，质谱，TGA-DTA和循环伏安研究进行了表征。它们的结构已经通过单晶X射线衍射分析确认。已经进行了一些理论计算以研究光谱跃迁。当已获得相应的醇和酮作为主要产物时，铜（II）配合物在过氧化氢的存在下对饱和烃（例如环己烷，甲苯和环戊烷）的氧化显示出有效的催化能力。然而，发现配合物2作为氧化催化剂
• Reactivity of cis-bis(acetylacetonato)dichlorotitanium(IV) towards hydroxy-containing ligands: isolation and characterisation of products †
  作者：P. Venkateshwara Rao、Chebrolu Pulla Rao、Elina K. Wegelius、Erkki Kolehmainen、Kari Rissanen

  DOI：10.1039/a906985b

  日期：——

  The reactivity of cis-[Ti(acac)2Cl2] with a number of OH containing ligands has been explored. Corresponding products have been synthesized, isolated and characterised. Three dimensional structures of some of the products were established by single crystal X-ray diffraction. The reactivity of these ligands towards non-oxo titanium centres has been found to be different from that of oxometal centres of VV, MoVI and UVI. All the products of TiIV isolated were mononuclear complexes possessing one or two ligands. Both the molecular and crystal structures of the titanium products are found to be different from those of the oxometal ones.

  我们探索了顺式-[Ti(acac)2Cl2] 与一些含 OH 的配体的反应性。合成、分离和表征了相应的产物。通过单晶 X 射线衍射，确定了一些产物的三维结构。发现这些配体对非氧钛中心的反应性与 VV、MoVI 和 UVI 的氧金属中心不同。所有分离出的 TiIV 产物都是拥有一个或两个配体的单核络合物。钛产物的分子结构和晶体结构都不同于氧金属产物。