4-{2-[2-(methoxyethoxy)ethoxy]ethoxy}salicylaldehyde | 1017574-81-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-{2-[2-(methoxyethoxy)ethoxy]ethoxy}salicylaldehyde
• 英文别名: 4-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}salicylaldehyde；2-Hydroxy-4-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzaldehyde；2-hydroxy-4-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzaldehyde
• CAS: 1017574-81-0
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: SSAKQSLDCVVZLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-{2-[2-(methoxyethoxy)ethoxy]ethoxy}salicylaldehyde 、 1,3-二氨基-2-羟基丙烷 以 甲醇 、 乙醇 为溶剂， 反应 48.0h， 生成 N,N'-1,3-bis[[2-hydroxy-4-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzylideneamino]propan-2-ol
  参考文献：
  名称：

  Evaluating Binuclear Copper(II) Complexes for Glycoside Hydrolysis

  摘要：

  Three binuclear copper(II) complexes were characterized as solids by X-ray diffraction and in solution by UV/vis spectrophotometric titration, and subsequently evaluated for their glycosidase-like activity. The structure analysis revealed comparable intermetallic Cu center dot center dot center dot Cu distances (similar to 3.5 angstrom) for the complexes 2 and 3. Despite this similarity, the composition of the complexes differs significantly in aqueous solution as revealed by spectrophotometric titrations. The hydrolysis of selected nitrophenylglycopyranosides is up to 11,000-fold accelerated over background in the presence of the copper(II) complexes in 3-(cyclohexylamino)-1-propanesulfonic acid (CAPS) buffer at pH 10.5 and 30 degrees C.

  DOI：

  10.1021/ic9014064
• 作为产物：
  描述：

  N,N'-1,3-bis[[2-hydroxy-4-[2-(2-methoxyethoxy)ethoxy]ethoxy]benzylideneamino]propan-2-ol 在 ammonium hydroxide 作用下， 反应 24.0h， 生成 4-{2-[2-(methoxyethoxy)ethoxy]ethoxy}salicylaldehyde
  参考文献：
  名称：

  Miniemulsion polymers as solid support for transition metal catalysts

  摘要：

  A pentadentate salen-type ligand was immobilized in a poly[(styrene)]-co-(butyl acrylate)] matrix by miniemulsion polymerization. The obtained polymer beads revealed a particle size of 50 nm in the dry state by transmission electron microscopy. Dynamic light scattering experiments in methanol and water showed a solvent-dependent average particle size with a mean particle diameter of up to 233 nm in methanol. These results provide valuable insights for the optimization of macromolecular oxidation catalysts and their future use as enzyme-like entities in aqueous media. The particle stability was demonstrated over a wide pH range (3-11) by gel permeation chromatography, and initial results for the metal ion binding ability were obtained. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2009.11.016

文献信息

• Manganese complexes with planar or tridimensional acyclic or cyclic Schiff base ligands
  作者：V. Peruzzo、S. Tamburini、P.A. Vigato

  DOI：10.1016/j.ica.2012.01.010

  日期：2012.5

  Abstract The coordination properties toward manganese(II) salts of a variety of [1 + 2], [2 + 1], [2 + 2] and [3 + 1] acyclic and cyclic ligands with different shapes and coordinating moieties have been studied. These ligands, obtained by condensation of suitable formyl- and primary amine precursors, give rise to mono- or dinuclear manganese(II) or manganese(III) complexes, characterized by elemental

  摘要研究了不同形状和配位部分的各种[1 + 2]，[2 + 1]，[2 + 2]和[3 +1]无环和环状配体对锰（II）盐的配位性能。这些配体是通过缩合合适的甲酰基和伯胺前体而获得的，生成单核或二核锰（II）或锰（III）配合物，其特征在于元素分析，红外光谱，ESI-MS光谱和X射线分析结构确定。特别是在[Mn（H 3 -L C2）（H 2 O）2]（Cl）（H 2 O）的结构中，平面的，可能成核的配体H 5 -L C2由[2 + 1]吡ido醛盐酸盐与1,3-二氨基-2-丙醇的缩合反应，中央八面体锰（III）离子位于[H 3 –LC2] 2-的N 2 O 2 Schiff碱部分中，它不作为隔间系统，因为中央酒精团不参与协调。在[Mn（H 3 -L A5）]·0.25H 2 O·CH 3 OH中，其中潜在的成核配体H 6 -LA5通过3-甲酰基水杨酸和三（氨基乙基）的[3 +1]缩合形成胺
• Regioselective alkylation of hydroxysalicylaldehydes
  作者：Moses G. Gichinga、Susanne Striegler

  DOI：10.1016/j.tet.2009.03.104

  日期：2009.6

  Schiff-base ligands are often used as backbone ligands for mono- and dinuclear complexes that serve as catalysts during aerobic oxidation reactions. However, their water Solubility is low and limits their applicability as catalysts to transform highly water-soluble biomolecules, such as carbohydrates or amino alcohols. A new method to regioselectively incorporate water solubility-promoting polyethylene glycol side chains into a frequently used aldehyde building block of Schiff-base ligands has been developed. (C) 2009 Elsevier Ltd. All rights reserved.
• Effect of Water on the Catalytic Oxidation of Catechols
  作者：Moses G. Gichinga、Susanne Striegler

  DOI：10.1021/ja078057+

  日期：2008.4.1

  A dinuclear copper(II) complex derived from a new water-soluble pentadentate Schiff base backbone ligand has been prepared and characterized in solution and in the solid state. The complex has been found to accelerate the aerobic oxidation of 3,5-di-tert-butylcatechol (DTBC) into 3,5-di-tert-butylquinone (DTBQ) by 5 orders of magnitude, compared to the background reaction in aqueous methanol (K-cat/k(non)= 160 000) at 30 degrees C. The transformation of the model substrate is considerably slower in pure methanol (k(cat)/k(non) = 60 000) under otherwise identical conditions. In-depth investigation of the catalytically active species revealed different structures for the copper(II) complex in methanol and in methanol/water mixtures.
• Evaluating Binuclear Copper(II) Complexes for Glycoside Hydrolysis
  作者：Susanne Striegler、Natasha A. Dunaway、Moses G. Gichinga、James D. Barnett、Anna-Gay D. Nelson

  DOI：10.1021/ic9014064

  日期：2010.3.15

  Three binuclear copper(II) complexes were characterized as solids by X-ray diffraction and in solution by UV/vis spectrophotometric titration, and subsequently evaluated for their glycosidase-like activity. The structure analysis revealed comparable intermetallic Cu center dot center dot center dot Cu distances (similar to 3.5 angstrom) for the complexes 2 and 3. Despite this similarity, the composition of the complexes differs significantly in aqueous solution as revealed by spectrophotometric titrations. The hydrolysis of selected nitrophenylglycopyranosides is up to 11,000-fold accelerated over background in the presence of the copper(II) complexes in 3-(cyclohexylamino)-1-propanesulfonic acid (CAPS) buffer at pH 10.5 and 30 degrees C.
• Miniemulsion polymers as solid support for transition metal catalysts
  作者：Moses G. Gichinga、Susanne Striegler、Natasha A. Dunaway、James D. Barnett

  DOI：10.1016/j.polymer.2009.11.016

  日期：2010.2

  A pentadentate salen-type ligand was immobilized in a poly[(styrene)]-co-(butyl acrylate)] matrix by miniemulsion polymerization. The obtained polymer beads revealed a particle size of 50 nm in the dry state by transmission electron microscopy. Dynamic light scattering experiments in methanol and water showed a solvent-dependent average particle size with a mean particle diameter of up to 233 nm in methanol. These results provide valuable insights for the optimization of macromolecular oxidation catalysts and their future use as enzyme-like entities in aqueous media. The particle stability was demonstrated over a wide pH range (3-11) by gel permeation chromatography, and initial results for the metal ion binding ability were obtained. (C) 2009 Elsevier Ltd. All rights reserved.