N-(6-(((pyridin-2-ylmethyl)amino)methyl)pyridin-2-yl)pivalamide | 831195-44-9

• 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-(6-(((pyridin-2-ylmethyl)amino)methyl)pyridin-2-yl)pivalamide
• 英文别名: N-(6-pivaloylamido-2-pyridylmethyl)-N-(2-pyridylmethyl)amine；2,2-dimethyl-N-[6-[(pyridin-2-ylmethylamino)methyl]pyridin-2-yl]propanamide
• CAS: 831195-44-9
• 化学式: C₁₇H₂₂N₄O
• 分子量: 298.388
• InChiKey: DAVPNBJVPKMEEO-UHFFFAOYSA-N

物化性质

• 沸点：
  489.2±45.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  66.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(6-(((pyridin-2-ylmethyl)amino)methyl)pyridin-2-yl)pivalamide 在 盐酸 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 96.0h， 生成 2,6-bis((((6-aminopyridin-2-yl)methyl)(pyridin-2-ylmethyl)-amino)methyl)-4-methylphenol
  参考文献：
  名称：

  Spectroscopic Characterization of the Active Fe^IIIFe^III and Fe^IIIFe^II Forms of a Purple Acid Phosphatase Model System

  摘要：

  Two new dinucleating ligands (H3L2 and HL3), derivatives of a well-known dinucleating ligand (HL1) with two bis-picolylamine sites connected to a bridging phenolate, with hydrogen-bonding donor groups at two of the pyridine moieties were designed and synthesized. Design of these ligands suggests that they will lead to dinuclear complexes with potential to stabilize phosphoester substrates as monodentate rather than bridging ligands. We report the diferric complexes [Fe-2(III)(H2L2)(OH)(4+) and [Fe-2(III)(L-3)(OH)(OH2)(2)](4+), which have been characterized by spectrophotometric titrations, UV-vis, IR, NMR, EPR, and Mossbauer spectroscopy. The phosphatase activity of the diferric systems, in addition to the partially reduced heterovalent [(FeFeII)-Fe-III(L-3)(OH)(OH2)(2)](3+) complex, has been investigated, and the complexes are shown to catalytically hydrolyze the activated phosphodiester substrate BDNPP (bis-dinitrophenylphosphate) as well as the corresponding phosphomonoester substrate DNPP (dinitrophenylphosphate). The results indicate that indeed the secondary interactions lead to an increase of the phosphatase activity and to active phosphomonoesterase catalysts. Interestingly, the heterovalent form of the HL3-based complex is more efficient than the diferric complex, and this is also discussed.

  DOI：

  10.1021/ic301347t
• 作为产物：
  描述：

  2-氨甲基吡啶 、 N-(6-甲酰基吡啶-2-基)三甲基乙酰胺 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以100%的产率得到N-(6-(((pyridin-2-ylmethyl)amino)methyl)pyridin-2-yl)pivalamide
  参考文献：
  名称：

  Spectroscopic Characterization of the Active Fe^IIIFe^III and Fe^IIIFe^II Forms of a Purple Acid Phosphatase Model System

  摘要：

  Two new dinucleating ligands (H3L2 and HL3), derivatives of a well-known dinucleating ligand (HL1) with two bis-picolylamine sites connected to a bridging phenolate, with hydrogen-bonding donor groups at two of the pyridine moieties were designed and synthesized. Design of these ligands suggests that they will lead to dinuclear complexes with potential to stabilize phosphoester substrates as monodentate rather than bridging ligands. We report the diferric complexes [Fe-2(III)(H2L2)(OH)(4+) and [Fe-2(III)(L-3)(OH)(OH2)(2)](4+), which have been characterized by spectrophotometric titrations, UV-vis, IR, NMR, EPR, and Mossbauer spectroscopy. The phosphatase activity of the diferric systems, in addition to the partially reduced heterovalent [(FeFeII)-Fe-III(L-3)(OH)(OH2)(2)](3+) complex, has been investigated, and the complexes are shown to catalytically hydrolyze the activated phosphodiester substrate BDNPP (bis-dinitrophenylphosphate) as well as the corresponding phosphomonoester substrate DNPP (dinitrophenylphosphate). The results indicate that indeed the secondary interactions lead to an increase of the phosphatase activity and to active phosphomonoesterase catalysts. Interestingly, the heterovalent form of the HL3-based complex is more efficient than the diferric complex, and this is also discussed.

  DOI：

  10.1021/ic301347t

文献信息

• Investigating the effect of hydrogen bonding environments in amide cleavage reactions at zinc(ii) complexes with intramolecular amide oxygen co-ordination
  作者：Juan C. Mareque Rivas、Emiliano Salvagni、Simon Parsons

  DOI：10.1039/b414223c

  日期：——

  ligands without hydrogen bonding groups (1,10-phenanthroline L5, 2-(aminomethyl)pyridine L6) as control compounds, and with an amino hydrogen bonding group (6-amino-2-(aminomethyl)pyridine L7) have been synthesised. Amide cleavage is in this case faster at the zinc(II) complex with the amino hydrogen bonding group. Thus, hydrogen bonding environments can both accelerate and slow down amide bond cleavage reactions

  酰胺键与氢键合微环境周围的锌（II）离子配位是金属蛋白酶的常见结构/功能特征。我们报告了两种策略将氢键基团定位在锌（II）结合的酰胺氧附近，并且我们研究了它们对酰胺基团稳定性的影响。多齿三脚架配体（6-R1-2-吡啶甲基）-R2（R1 = NHCOtBu，R2 = N（CH2-py-6-X）2 X = H L1，X = NH2，H L2，X = NH2 L3）形式[（L）Zn] 2+阳离子（L = L1，1; L2，2; L3，3）带有分子内酰胺氧配位（1-3）和分子内NH ... O = C（酰胺）氢由配体骨架牢固固定的键（2，3）。当在50（1）摄氏度下在甲醇中添加Me4NOH.5H2O（1当量）时，1-3进行叔丁基酰胺的裂解。在这些条件下，酰胺的半衰期t（1/2）粘结时间为0.4 h，持续1 2小时9小时，3小时320小时。（6-NHCOtBu-2-吡啶基甲基）-R2（R2 = N（
• Asymmetric mono- and dinuclear Ga III and Zn II complexes as models for purple acid phosphatases
  作者：Simone Bosch、Peter Comba、Lawrence R. Gahan、Gerhard Schenk

  DOI：10.1016/j.jinorgbio.2015.12.028

  日期：2016.9

  Derivatives of the known dinucleating ligands HL1 (2,6-bis[bis(pyridin-2-ylmethyl)amino]methyl}-4-methylphenol) and H2L2 (2-([bis(pyridin-2-ylmethyl)amino]methyl}-6-([(2-hydroxybenzyl)(pyridine-2-ylmethyl)amino]methyl}-4-methylphenol) with two pivaloylamido hydrogen bond donor substituents, H3L3 and H3L5, have been prepared. The mono-, homo- and heterodinuclear Zn-II and Ga-III complexes of these ligands have been prepared and characterized. The solution equilibria are discussed on the basis of extensive NMR spectroscopic, mass spectrometric and pH-dependent UV-vis spectroscopic titrations. The phosphoester hydrolysis activity of the complexes has been studied as a function of pH and substrate concentration and analyzed using Michaelis-Menten kinetics. It emerges that the mixed metal (mixed valent) complex of the ligand with an asymmetric disposition of the hydrogen bonding substituents (H3L3) is a functional model for the mixed valent, dinuclear metallohydrolase purple add phosphatase. This complex combines the essential structural features of the active site of PAP and is the first heterodinuclear model complex mimicking the essential function of PAPs, i.e. the hydrolysis of phosphomonoesters. (C) 2015 Elsevier Inc All rights reserved.
• NEAR INFRARED ABSORBING COMPOSITION, NEAR INFRARED CUT FILTER, METHOD OF MANUFACTURING NEAR INFRARED CUT FILTER, DEVICE, METHOD OF MANUFACTURING COPPER-CONTAINING POLYMER, AND COPPER-CONTAINING POLYMER
  申请人：FUJIFILM Corporation

  公开号：US20180094086A1

  公开（公告）日：2018-04-05

  The near infrared absorbing composition includes: a copper-containing polymer having a copper complex site at a polymer side chain; and a solvent, in which the copper complex site includes a site multidentate-coordinated to a copper atom and at least one selected from the group consisting of a site monodentate-coordinated to a copper atom and a counter ion to a copper complex skeleton, and a polymer main chain and a copper atom at the copper complex site are bonded to each other through the site monodentate-coordinated to a copper atom or the counter ion.
• Spectroscopic Characterization of the Active Fe^IIIFe^III and Fe^IIIFe^II Forms of a Purple Acid Phosphatase Model System
  作者：Peter Comba、Lawrence R. Gahan、Valeriu Mereacre、Graeme R. Hanson、Annie K. Powell、Gerhard Schenk、Marta Zajaczkowski-Fischer

  DOI：10.1021/ic301347t

  日期：2012.11.19

  Two new dinucleating ligands (H3L2 and HL3), derivatives of a well-known dinucleating ligand (HL1) with two bis-picolylamine sites connected to a bridging phenolate, with hydrogen-bonding donor groups at two of the pyridine moieties were designed and synthesized. Design of these ligands suggests that they will lead to dinuclear complexes with potential to stabilize phosphoester substrates as monodentate rather than bridging ligands. We report the diferric complexes [Fe-2(III)(H2L2)(OH)(4+) and [Fe-2(III)(L-3)(OH)(OH2)(2)](4+), which have been characterized by spectrophotometric titrations, UV-vis, IR, NMR, EPR, and Mossbauer spectroscopy. The phosphatase activity of the diferric systems, in addition to the partially reduced heterovalent [(FeFeII)-Fe-III(L-3)(OH)(OH2)(2)](3+) complex, has been investigated, and the complexes are shown to catalytically hydrolyze the activated phosphodiester substrate BDNPP (bis-dinitrophenylphosphate) as well as the corresponding phosphomonoester substrate DNPP (dinitrophenylphosphate). The results indicate that indeed the secondary interactions lead to an increase of the phosphatase activity and to active phosphomonoesterase catalysts. Interestingly, the heterovalent form of the HL3-based complex is more efficient than the diferric complex, and this is also discussed.