2-(2-(pyridin-2-yl)tetrahydropyrimidin-1(2H)-yl)-N-(pyridin-2-ylmethylene)ethanamine | 870992-38-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-(2-(pyridin-2-yl)tetrahydropyrimidin-1(2H)-yl)-N-(pyridin-2-ylmethylene)ethanamine
• 英文别名: N-(1-pyridin-2-ylmethylene)-N-[2-(2-pyridin-2-yltetrahydropyrimidin-1(2H)-yl)ethyl]amine；1-pyridin-2-yl-N-[2-(2-pyridin-2-yl-1,3-diazinan-1-yl)ethyl]methanimine
• CAS: 870992-38-4
• 化学式: C₁₇H₂₁N₅
• 分子量: 295.387
• InChiKey: FCDFKXCLYLXTKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  manganese(II) chloride tetrahydrate 、 2-(2-(pyridin-2-yl)tetrahydropyrimidin-1(2H)-yl)-N-(pyridin-2-ylmethylene)ethanamine 以 甲醇 为溶剂， 反应 0.5h， 以0.674 g的产率得到
  参考文献：
  名称：

  Selective coordination of multidentate ligands in manganese(II) complexes: Syntheses, structures and phenoxazinone synthase mimicking activity

  摘要：

  The present report describes the syntheses, structures and catalytic activity mimicking the function of phenoxazinone synthase of four new mononuclear manganese(II) complexes, [Mn(L-1)Cl-2] (1), [Mn(L-2)Cl-2] (2), [Mn(L-3)Cl-2] (3) and [Mn(L-4)Cl-2]center dot H2O (4), derived from the multidentate ligands L-1-L-4, which are the 1:2 condensation products of triamines (or tetraamine) and 2-pyridinecarboxaldehyde (or 6-methyl-2-pyridinecarboxaldehyde). X-ray crystallography reveals the preferential coordination ability of all the ligands (cyclic isomers over the acyclic analogues) to a common metal center (Mn2+) and in one case (2) methanol addition across the -C=N- bond. All the complexes show moderate phenoxazinone synthase activity and the experimental data suggest that a correlation can be drawn between E-1/2 and V-max of the complexes, namely the lower the E-1/2 value the higher the catalytic activity. The effect of methyl substitution on the pyridine ring (in 3) on the matrix parameters and on the phenoxazinone synthase activity is also noticeable. The ESI-MS positive spectrum of a mixture of a representative complex (1 or 4) and o-aminophenol shows a peak corresponding to [Mn(L)(OAP)](+) (OAPH = o-aminophenol), suggesting that the catalytic activity proceeds through the formation of a stable complex-substrate intermediate. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.05.017
• 作为产物：
  描述：

  吡啶-2-甲醛 、 N-(2-乙氨基)-1,3-丙二胺 以 甲醇 为溶剂， 反应 0.5h， 生成 2-(2-(pyridin-2-yl)tetrahydropyrimidin-1(2H)-yl)-N-(pyridin-2-ylmethylene)ethanamine
  参考文献：
  名称：

  Selective coordination of multidentate ligands in manganese(II) complexes: Syntheses, structures and phenoxazinone synthase mimicking activity

  摘要：

  The present report describes the syntheses, structures and catalytic activity mimicking the function of phenoxazinone synthase of four new mononuclear manganese(II) complexes, [Mn(L-1)Cl-2] (1), [Mn(L-2)Cl-2] (2), [Mn(L-3)Cl-2] (3) and [Mn(L-4)Cl-2]center dot H2O (4), derived from the multidentate ligands L-1-L-4, which are the 1:2 condensation products of triamines (or tetraamine) and 2-pyridinecarboxaldehyde (or 6-methyl-2-pyridinecarboxaldehyde). X-ray crystallography reveals the preferential coordination ability of all the ligands (cyclic isomers over the acyclic analogues) to a common metal center (Mn2+) and in one case (2) methanol addition across the -C=N- bond. All the complexes show moderate phenoxazinone synthase activity and the experimental data suggest that a correlation can be drawn between E-1/2 and V-max of the complexes, namely the lower the E-1/2 value the higher the catalytic activity. The effect of methyl substitution on the pyridine ring (in 3) on the matrix parameters and on the phenoxazinone synthase activity is also noticeable. The ESI-MS positive spectrum of a mixture of a representative complex (1 or 4) and o-aminophenol shows a peak corresponding to [Mn(L)(OAP)](+) (OAPH = o-aminophenol), suggesting that the catalytic activity proceeds through the formation of a stable complex-substrate intermediate. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.05.017

文献信息

• Complexation to Fe^II, Ni^II, and Zn^II of Multidentate Ligands Resulting from Condensation of 2-Pyridinecarboxaldehyde with α,ω-Triamines:  Selective Imidazolidine/Hexahydropyrimidine Ring Opening Revisited
  作者：Nicolas Bréfuel、Christine Lepetit、Sergiu Shova、Françoise Dahan、Jean-Pierre Tuchagues

  DOI：10.1021/ic050791b

  日期：2005.11.1

  one imidazolidine ring and one (short) ethylene bridge. L(A) acts as a tetradentate ligand yielding [Fe(II)L(A)(NCS)2] (1), [Ni(II)L(A)(NCS)2] (4), and [Zn(II)L(A)(NCS)2] (7). The template effect of the metal center is selective toward the ligand L(B)/L(B*) including a hexahydropyrimidine (imidazolidine) ring and the shorter ethylene (longer propylene) bridge. The Fe(II) cation is small enough to exert

  2-吡啶甲醛与二亚乙基三胺，3-[（（2-氨基乙基）氨基]丙胺和3,3'-亚氨基双（丙胺）的摩尔比为2：1的缩合反应可生成仅在不对称（环）异构形式L（A），L（B）/ L（B *）和L（C）。金属中心（Fe（II），Ni（II）和Zn（II））的模板作用导致L（C）的开环，该开环包括一个六氢嘧啶环和一个（长）丙烯桥。生成的对称双席夫碱异构体形式L（C'）通过五配位稳定，得到[Fe（II）L（C'）（NCS）]（NCS）（3），[Ni（II）L（C' ）（NCS）]（NCS）（6）和[Zn（II）L（C'）（NCS）]（NCS）（9）。相同的金属中心太大，无法对L（A）施加模板效应，包括一个咪唑烷环和一个（短）乙烯桥。L（A）作为四齿配体，产生[Fe（II）L（A）（NCS）2]（1），[Ni（II）L（A）（NCS）2]（4）和[Zn（ II）L（A）（NCS）2]（7）。金属中心的模板作
• Complexation to Cadmium(II) of a Tetradentate Ligand Resulting from the Condensation of 2-Pyridinecarbaldehyde with N-(2- Aminoethyl)propane-1,3-diamine
  作者：Mohammad Hakimi、Zahra Mardani、Keyvan Moeini、Esther Schuh、Fabian Mohr

  DOI：10.5560/znb.2013-2294

  日期：2013.3.1

  The reaction of 2-pyridinecarbaldehyde with N-(2-aminoethyl)propane-1,3-diamine in a 2 : 1 molar ratio under microwave irradiation gave 2-(2-(pyridin-2-yl)-tetrahydropyrimidin-1(2H)-yl)-N- (pyridin-2-ylmethylene)ethanamine (L) as a mixture with the isomer 3-(2-(pyridin-2-yl)imidazolidin- 1-yl)-N-(pyridin-2-ylmethylene)propan-1-amine (L*). The molecules were characterized by elemental analyses and spectroscopic methods. Percentages of L and L* were evaluated through integration of selected ¹H NMR signals. The cadmium iodide complex of L, [Cd(L)I₂]·H₂O (1), was prepared and identified by elemental analysis, FT-IR, Raman, and ¹H NMR spectroscopy, and single-crystal X-ray diffraction. In the crystal structure of 1 the cadmium atom with four coordinated nitrogen atoms and two iodide ions has a distorted octahedral geometry. A water molecule is also incorporated in the crystal network. Several hydrogen bonds including N-H···O, C-H···O, C-H···I, and O-H···I interactions are present in the crystal structure of 1.

  在微波辐射下，2-吡啶甲醛与N-(2-氨基乙基)丙烷-1,3-二胺以2:1摩尔比反应，生成2-(2-(吡啶-2-基)-四氢嘧啶-1(2H)-基)-N-(吡啶-2-基亚甲基)乙胺(L)和同分异构体3-(2-(吡啶-2-基)咪唑啉-1-基)-N-(吡啶-2-基亚甲基)丙胺(L*)的混合物。这些分子通过元素分析和光谱方法进行了表征。通过选择性1H NMR信号的积分评估了L和L*的百分比。L的碘化镉配合物[Cd(L)I2]·H2O(1)通过元素分析、FT-IR、拉曼和1H NMR光谱以及单晶X射线衍射进行了制备和鉴定。在1的晶体结构中，镉原子具有四个配位氮原子和两个碘离子，呈扭曲的八面体几何构型。水分子也被并入晶体网络中。晶体结构中存在几个氢键，包括N-H···O、C-H···O、C-H···I和O-H···I相互作用。
• Selective coordination of multidentate ligands in manganese(II) complexes: Syntheses, structures and phenoxazinone synthase mimicking activity
  作者：Anangamohan Panja

  DOI：10.1016/j.poly.2014.05.017

  日期：2014.9

  The present report describes the syntheses, structures and catalytic activity mimicking the function of phenoxazinone synthase of four new mononuclear manganese(II) complexes, [Mn(L-1)Cl-2] (1), [Mn(L-2)Cl-2] (2), [Mn(L-3)Cl-2] (3) and [Mn(L-4)Cl-2]center dot H2O (4), derived from the multidentate ligands L-1-L-4, which are the 1:2 condensation products of triamines (or tetraamine) and 2-pyridinecarboxaldehyde (or 6-methyl-2-pyridinecarboxaldehyde). X-ray crystallography reveals the preferential coordination ability of all the ligands (cyclic isomers over the acyclic analogues) to a common metal center (Mn2+) and in one case (2) methanol addition across the -C=N- bond. All the complexes show moderate phenoxazinone synthase activity and the experimental data suggest that a correlation can be drawn between E-1/2 and V-max of the complexes, namely the lower the E-1/2 value the higher the catalytic activity. The effect of methyl substitution on the pyridine ring (in 3) on the matrix parameters and on the phenoxazinone synthase activity is also noticeable. The ESI-MS positive spectrum of a mixture of a representative complex (1 or 4) and o-aminophenol shows a peak corresponding to [Mn(L)(OAP)](+) (OAPH = o-aminophenol), suggesting that the catalytic activity proceeds through the formation of a stable complex-substrate intermediate. (C) 2014 Elsevier Ltd. All rights reserved.