N,N'-bis(2-pyridylmethyl)-1,3-diaminopropan-2-ol*4HCl | 276867-58-4

• 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)-1,3-diaminopropan-2-ol*4HCl
• 英文别名: N,N'-bis(2-pyridylmethyl)-1,3-diaminopropan-2-ol；N,N'-bis(2-pyridylmethyl)-1,4-diaminobutan-2-ol；N,N'-(2-pyridylmethyl)-1,3-propanediamine-2-ol；1,3-bis[(pyridin-2-ylmethyl)amino]propan-2-ol；1,3-Bis(pyridin-2-ylmethylamino)propan-2-ol
• CAS: 276867-58-4
• 化学式: C₁₅H₂₀N₄O
• 分子量: 272.35
• InChiKey: XGTUFCCHYLMIOE-UHFFFAOYSA-N

物化性质

• 沸点：
  487.3±45.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(氯甲基)-2-羟基-5-甲基苯甲醛 、 N,N'-bis(2-pyridylmethyl)-1,3-diaminopropan-2-ol*4HCl 以 二氯甲烷 为溶剂， 反应 12.0h， 以60%的产率得到3-[[[3-[(3-Formyl-2-hydroxy-5-methylphenyl)methyl-(pyridin-2-ylmethyl)amino]-2-hydroxypropyl]-(pyridin-2-ylmethyl)amino]methyl]-2-hydroxy-5-methylbenzaldehyde
  参考文献：
  名称：

  新型三核铜（II）配合物的合成，结构，磁性以及水解酶和儿茶酚酶活性

  摘要：

  摘要本文报道了新的多齿N，O-供体配体H3L_2pyald =（N，N'-双-（2-吡啶基甲基）-（2-羟基-3-羰基-5-甲基苄基）-1， 3-丙二胺-2-醇）及其第一个三核铜（II）络合物[Cu3（L_2pyald）（μ-OAc）]（ClO4）2（1）。1的结构由X射线晶体学确定，温度范围为4–300 K的可变温度磁数据表明Cu（1）和Cu（2）之间的反铁磁性很弱（J1,2≅-1.0 cm-1） ）的中心由μ-烷氧基和μ-乙酸酯基和弱铁磁耦合（J1,3 = J2,3≅+ 4.0 cm-1）桥接，涉及{Cu（1）（μ-phenoxo）Cu（3）}和{Cu（2）（μ-phenoxo）Cu（3）}结构单元。配合物1对模型底物双（2,4-二硝基苯基）磷酸酯（2，4-BDNPP）和邻苯二酚氧化酶活性，因为它可以有效地催化双氧将3,5-二叔丁基邻苯二酚氧化为3,5-二叔丁基-邻苯醌。1与它的双核母

  DOI：

  10.1016/j.ica.2015.06.023
• 作为产物：
  描述：

  吡啶-2-甲醛 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 22.0h， 生成 N,N'-bis(2-pyridylmethyl)-1,3-diaminopropan-2-ol*4HCl
  参考文献：
  名称：

  新型三核铜（II）配合物的合成，结构，磁性以及水解酶和儿茶酚酶活性

  摘要：

  摘要本文报道了新的多齿N，O-供体配体H3L_2pyald =（N，N'-双-（2-吡啶基甲基）-（2-羟基-3-羰基-5-甲基苄基）-1， 3-丙二胺-2-醇）及其第一个三核铜（II）络合物[Cu3（L_2pyald）（μ-OAc）]（ClO4）2（1）。1的结构由X射线晶体学确定，温度范围为4–300 K的可变温度磁数据表明Cu（1）和Cu（2）之间的反铁磁性很弱（J1,2≅-1.0 cm-1） ）的中心由μ-烷氧基和μ-乙酸酯基和弱铁磁耦合（J1,3 = J2,3≅+ 4.0 cm-1）桥接，涉及{Cu（1）（μ-phenoxo）Cu（3）}和{Cu（2）（μ-phenoxo）Cu（3）}结构单元。配合物1对模型底物双（2,4-二硝基苯基）磷酸酯（2，4-BDNPP）和邻苯二酚氧化酶活性，因为它可以有效地催化双氧将3,5-二叔丁基邻苯二酚氧化为3,5-二叔丁基-邻苯醌。1与它的双核母

  DOI：

  10.1016/j.ica.2015.06.023

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。
• Crystal structure, solution properties and hydrolytic activity of an alkoxo-bridged dinuclear copper(ii) complex, as a ribonuclease model
  作者：Tamás Gajda、Attila Jancsó、Satu Mikkola、Harri Lönnberg、Holger Sirges

  DOI：10.1039/b108948j

  日期：——

  Crystal structures, solution properties and ribonuclease activity of copper(II) complexes of a binucleating, bis-pyridyl ligand (N,N′-bis(2-pyridylmethyl)-1,3-diaminopropan-2-ol, L) have been investigated. The single-crystal X-ray structure of the mononuclear complex [CuL(ClO4)2] (1) shows distorted octahedral geometry around the metal ion, with the four nitrogens of the ligand in the equatorial plane of copper(II). A μ-alkoxo-bridged dinuclear complex is formed in the presence of a two-fold metal excess. Despite the symmetrical ligand, the two metal ions in [Cu2(LH−1)(DPP)(ClO4)(CH3OH)]ClO4 (2, DPP = diphenyl phosphate) have distinct, distorted octahedral (Cu1) and square pyramidal (Cu2) geometry. Beside the alkoxo-oxygen, the phosphate group of DPP also bridges the two metal centers in 2 in a μ-1,3-bridging mode. The complexes formed in aqueous solution are likely to have analogous structures to 1 and 2. The dinuclear [Cu2(LH−1)(OH)] complex efficiently promotes the hydrolysis/transesterification of both activated (2-hydroxypropyl p-nitrophenyl phosphate, hpnp) and non-activated, biological phosphodiesters (uridine-2′,3′-cyclic-monophosphate, cUMP and uridylyl-(3′,5′)-uridine, UpU). For example, a 2 mM solution of the dinuclear complex provides 5 orders of magnitude acceleration in the hydrolysis of cUMP. The proposed mechanisms include double Lewis-acid activation with intramolecular general base catalysis.

  我们研究了双核双吡啶配体（N,N′-双（2-吡啶基甲基）-1,3-二氨基丙-2-醇，L）的铜（II）配合物的晶体结构、溶液性质和核糖核酸酶活性。单核复合物 [CuL(ClO4)2] (1) 的单晶 X 射线结构显示出金属离子周围的扭曲八面体几何形状，配体的四个硝基位于铜（II）的赤道面上。在金属过量两倍的情况下，形成了一个μ-烷氧基桥接的双核配合物。尽管配体是对称的，但[Cu2(LH-1)(DPP)( )(CH3OH)] （2，DPP = 磷酸二苯酯）中的两个金属离子具有不同的扭曲八面体（Cu1）和正方金字塔（Cu2）几何形状。除了烷氧基外，DPP 的磷酸基团还以μ-1,3 桥接模式桥接 2 中的两个金属中心。在水溶液中形成的配合物可能具有与 1 和 2 类似的结构。双核[Cu2(LH-1)(OH)]配合物能有效地促进活化的（2-羟基丙基对硝基苯磷酸酯，hpnp）和非活化的生物磷酸二酯（尿苷-2′,3′-环状单磷酸酯，cUMP 和尿苷-(3′,5′)-尿苷，UpU）的水解/酯化。例如，2 mM 的双核复合物溶液可使 cUMP 的水解速度加快 5 个数量级。提出的机理包括分子内通用碱催化的双路易斯酸活化。
• 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。
• 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.
• Mazurek, Waldemar; Kennedy, Brendan J.; Murray, Keith S., Inorganic Chemistry, 1985, vol. 24, # 20, p. 3258 - 3264
  作者：Mazurek, Waldemar、Kennedy, Brendan J.、Murray, Keith S.、O'Connor, Maxwell J.、Rodgers, John R.、Snow, Michael R.、Wedd, Anthony G.、Zwack, Peter R.

  DOI：——

  日期：——