N,N'-bis(2-pyridylmethyl)-1,4-diaminobutan-2-ol | 1217292-59-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N,N'-bis(2-pyridylmethyl)-1,4-diaminobutan-2-ol
• 英文别名: 1,4-Bis(pyridin-2-ylmethylamino)butan-2-ol；1,4-bis(pyridin-2-ylmethylamino)butan-2-ol
• CAS: 1217292-59-5
• 化学式: C₁₆H₂₂N₄O
• 分子量: 286.377
• InChiKey: LNWCQBYDBCHCDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  70.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,4-bis((pyridin-2-ylmethylene)amino)butan-2-ol 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以320 mg的产率得到N,N'-bis(2-pyridylmethyl)-1,4-diaminobutan-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

文献信息

• CHIRAL BINUCLEAR METAL COMPLEXES FOR STEREOSELECTIVE GLYCOSIDE HYDROLYSIS OF SACCHARIDES
  申请人：BOARD OF TRUSTEES OF THE UNIVERSITY OF ARKANSAS

  公开号：US20170275303A1

  公开（公告）日：2017-09-28

  Disclosed herein is a class of chiral binuclear metal complexes for stereoselective glycoside hydrolysis of saccharides, and more particular chiral binuclear transition metal complex catalysts that discriminate epimeric glycosides and α- and β-glycosidic bonds of saccharides in aqueous solutions at near physiological pHs. The chiral binuclear metal complexes include a Schiff-base-type ligand derived from a chiral diamino building block, and a binuclear transition metal core, each which can be varied for selectivity. The metal core is a Lewis-acidic metal ion, such as copper, zinc, lanthanum, iron and nickel. The Schiff-base may be a reduced or non-reduced Schiff-base derived from aliphatic linear, aliphatic cyclic diamino alcohols or aromatic aldehydes. The ligand can be a penta- or heptadentate ligand derived from pyridinecarbaldehydes, benzaldehydes, linear or cyclic diamines or diamino alcohols.

  本文揭示了一类手性双核金属配合物，用于在接近生理pH值的水溶液中对糖类进行立体选择性水解，更具体地说，是手性双核过渡金属配合物催化剂，可以区分糖类的对映异构体和α-和β-糖苷键。这些手性双核金属配合物包括来源于手性二胺建筑块的席夫碱型配体和双核过渡金属核心，每个都可以根据选择性进行变化。金属核心是一种路易斯酸性金属离子，例如铜、锌、镧、铁和镍。席夫碱可以是从脂肪线性、脂肪环状二胺醇或芳香醛衍生的还原或非还原的席夫碱。配体可以是从吡啶甲醛、苯甲醛、线性或环状二胺或二胺醇衍生的五齿或七齿配体。
• Chiral binuclear metal complexes for stereoselective hydrolysis of saccharides and glycosides
  申请人：BOARD OF TRUSTEES OF THE UNIVERSITY OF ARKANSAS

  公开号：US10870103B2

  公开（公告）日：2020-12-22

  Disclosed herein is a class of chiral binuclear metal complexes for stereoselective hydrolysis of saccharides and glycosides, and more particular chiral binuclear transition metal complex catalysts that discriminate epimeric glycosides and α- and β-glycosidic bonds of saccharides in aqueous solutions at near physiological pHs. The chiral binuclear metal complexes include a Schiff-base-type ligand derived from a chiral diamino building block, and a binuclear transition metal core, each which can be varied for selectivity. The metal core is a Lewis-acidic metal ion, such as copper, zinc, lanthanum, iron and nickel. The Schiff-base may be a reduced or non-reduced Schiff-base derived from aliphatic linear, aliphatic cyclic diamino alcohols or aromatic aldehydes. The ligand can be a penta- or heptadentate ligand derived from pyridinecarbaldehydes, benzaldehydes, linear or cyclic diamines or diamino alcohols.

  本文公开了一类用于立体选择性水解糖类和苷类的手性双核金属配合物，尤其是手性双核过渡金属配合物催化剂，该催化剂可在接近生理 pH 值的水溶液中分辨糖类的外嵌糖苷和 α 和 β-糖苷键。手性双核金属配合物包括一个由手性二氨基结构单元衍生的希夫碱配体和一个双核过渡金属核心，每个配体的选择性都可以改变。金属核为路易斯酸性金属离子，如铜、锌、镧、铁和镍。希夫碱可以是还原型或非还原型希夫碱，由脂肪族线性、脂肪族环状二元醇或芳香族醛衍生而来。配体可以是五齿或七齿配体，由吡啶羧醛、苯醛、线性或环状二胺或二元醇衍生而来。
• CHIRAL BINUCLEAR METAL COMPLEXES FOR STEREOSELECTIVE HYDROLYSIS OF SACCHARIDES AND GLYCOSIDES
  申请人：BOARD OF TRUSTEES OF THE UNIVERSITY OF ARKANSAS

  公开号：US20210101138A1

  公开（公告）日：2021-04-08

  Disclosed herein is a class of chiral binuclear metal complexes for stereoselective hydrolysis of saccharides and glycosides, and more particular chiral binuclear transition metal complex catalysts that discriminate epimeric glycosides and α- and β-glycosidic bonds of saccharides in aqueous solutions at near physiological pHs. The chiral binuclear metal complexes include a Schiff-base-type ligand derived from a chiral diamino building block, and a binuclear transition metal core, each which can be varied for selectivity. The metal core is a Lewis-acidic metal ion, such as copper, zinc, lanthanum, iron and nickel. The Schiff-base may be a reduced or non-reduced Schiff-base derived from aliphatic linear, aliphatic cyclic diamino alcohols or aromatic aldehydes. The ligand can be a penta- or heptadentate ligand derived from pyridinecarbaldehydes, benzaldehydes, linear or cyclic diamines or diamino alcohols.
• 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.