2,6-Bis(2-formylphenoxymethyl)pyridine | 66433-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,6-Bis(2-formylphenoxymethyl)pyridine
• 英文别名: 2,6-Bis-(2-formyl-phenoxymethyl)-pyridine；2-[[6-[(2-formylphenoxy)methyl]pyridin-2-yl]methoxy]benzaldehyde
• CAS: 66433-95-2
• 化学式: C₂₁H₁₇NO₄
• 分子量: 347.37
• InChiKey: UOXYFPDMCLNCND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-Bis(2-formylphenoxymethyl)pyridine 在 sodium tetrahydroborate 、 Ba⁽²⁺⁾*ClO₄^(1-)=BaClO₄⁽¹⁺⁾ 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 2-[3.25-dioxa-11.14.17.31-tetraazatetracyclo[25.3.1.O(4.9).O(19.24)]hentriaconta-1(31).4(9).5.7.10.17.19(24).20.22.27.29-nonaen-14-yl]-1-athanamine
  参考文献：
  名称：

  一类新的含 NxOypyridine 的大环化合物：它们的 Y(III)、Ln(III)、Zn(II) 和 Cd(II) 配位化合物的合成和表征

  摘要：

  2,6-双(2-甲酰基苯氧基甲基)吡啶与N,N-双(3-氨基丙基)甲胺或三(2-氨基乙基)胺之间的反应已被用作合成七个氧杂氮杂大环配体的起始点，其中五人以前从未报道过。它们都具有不同的吊臂，提供了广泛的协调可能性。席夫碱大环 L1 和 L4 及其还原配体 L2 和 L5 分别衍生自 2,6-双（2-甲酰基苯氧基甲基）吡啶和三（2-氨基乙基）胺或 N,N-双（3-氨基丙基）甲胺. L1 与水杨醛反应形成 L3，其特征是悬臂中有一个亚胺键。通过用甲基-咪唑或甲基-吲哚对游离 NH 基团进行烷基化，配体 L5 已成为悬垂臂 L6 和 L7 的前体。通过模板或非模板方法，我们已经用 Y(III)、Ln(III)、Zn(II) 和 Cd(II) 阳离子合成了不同的单核和双核配合物。游离的大环配体及其相应的元...

  DOI：

  10.1139/v03-214
• 作为产物：
  描述：

  2,6-吡啶二甲醇 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2,6-Bis(2-formylphenoxymethyl)pyridine
  参考文献：
  名称：

  Metal-ion selectivity by macrocyclic ligands. Part 1. The interaction of Ni II and Cu II with pyridinyl-derived N3O2 macrocycles; the X-ray structures of a free macrocycle, its endomacrocyclic complexes of Ni II and Cu II and an exomacrocyclic nickel(II) complex

  摘要：

  The interaction of Cu(II) and Ni(II) with two macrocycles L1 and L2, each containing an N3O2 donor set, has been investigated. Spectrophotometric studies in dimethyl sulphoxide reveal the formation of complexes with 1:1 and 1:2 metal:ligand ratios and conductometric studies in the same solvent indicated that all of the complexes were 1:2 electrolytes. Conductometric titration of the 1:1 copper(II) complexes with chloride in each case indicated the formation of a 1:1 electrolyte, presumably through co-ordination of a chloride ion to the central copper of each complex. Similar titration of the nickel(II) complexes gave evidence for the formation of dinuclear species; each of these was postulated to contain a bridging chloride anion. The stability constants of the complexes together with their enthalpies of co-ordination have been determined in 95% methanol. Extraction and related transport experiments were carried out and under the conditions employed Cu(II) was favoured over Ni(II). The X-ray crystal structures of the free macrocycle L1, the 1:1 complexes [CuL1(H2O)][ClO4]2 and [NiL1(l)]l.MeOH, and the 1:2 complex [NiL2(1)(NO3)]NO3.2MeOH have been determined. The metal in [CuL1(H2O)][ClO4]2 is six-co-ordinate and lies within the folded macrocyclic cavity. The donor set comprises the five macrocyclic donor atoms and a water molecule. Overall, the co-ordination sphere corresponds to a restricted tetragonal rhombic arrangement. The complex [NiL1(l)]l.MeOH also has all donors of the macrocycle co-ordinated with an iodide anion occupying the sixth site to yield a distorted-octahedral geometry. The structure of [NiL2(1)(NO3)]NO3.2MeOH shows that the nickel is again six-co-ordinated, to the aliphatic nitrogen atoms from two macrocycles (each showing exo co-ordination) and a bidentate nitrate anion.

  DOI：

  10.1039/dt9910000627

文献信息

• Synthesis of New Benzo-substituted Macrocyclic Ligands Containing Pyridine or Triazole as Subcyclic Units
  作者：Ahmed H.M Elwahy、Ashraf A Abbas

  DOI：10.1016/s0040-4020(99)01068-6

  日期：2000.2

  The macrocyclic diamides 11–21, 42 and 43 were prepared by nucleophilic reaction of the bis phenols 22–29 with the appropriate dihalo compounds 2, 3, 40 and 41, respectively. The macrocyclic dithiodiamides 30–33 were obtained in good yields upon treatment of 11, 13, 15 and 17 with Lawesson's reagent. The macrocycles 61–63 were prepared by condensation of the bis(aldehyde) 37 with the appropriate bis(aminotriazoles)

  大环二酰胺11 - 21，42和43是由双酚的亲核反应而制备22 - 29用适当的二卤代化合物2，3，40和41分别。大环dithiodiamides 30 - 33在处理后的良好的产率得到11，13，15和17与Lawesson试剂。大环61 – 63是通过双（醛）缩合制备的37用适当的双（氨基三唑）50 – 54生成相应的席夫碱56 – 60，然后用NaBH 4还原。
• Synthesis, Structural Characterization and Metal Inclusion Properties of 18-, 20- and 22-Membered Oxaazacyclophanes and Oxaazacalix[4]arene Analogues: Macrocyclic Amine and Schiff Base Receptors with Variable NxOy Donor Sets
  作者：Ramón Moreno-Corral、Herbert Höpfl、Lorena Machi-Lara、Karen O. Lara

  DOI：10.1002/ejoc.201001312

  日期：2011.4

  series of oxaazacyclophanes and oxaazacalix[4]arene analogues with 18-, 20- and 22-membered rings have been synthesized from diamine and dialdehyde building blocks and structurally characterized by spectroscopic methods. One diamine precursor and four macrocycles have additionally been analysed by single-crystal X-ray diffraction. Two of the oxaazacalix[4]arene analogues were employed for metal ion complexation

  已经从二胺和二醛结构单元合成了一系列具有 18、20 和 22 元环的氧氮杂环芳烃和氧氮杂杯 [4] 芳烃类似物，并通过光谱方法对其进行了结构表征。还通过单晶 X 射线衍射分析了一种二胺前体和四种大环。两种氧氮杂杯[4]芳烃类似物用于基于紫外/可见吸收光谱的金属离子络合研究，表明这两种化合物都能够与 Cu2+ 和 Zn2+ 形成络合物。
• Experimental and theoretical study on the regioselective synthesis and reaction of some bis- and poly(3-mercapto-1,2,4-triazin-5(4H)-one) derivatives
  作者：Hadeer M. Diab、Walid M.I. Hassan、Ismail A. Abdelhamid、Ahmed H.M. Elwahy

  DOI：10.1016/j.molstruc.2019.07.047

  日期：2019.12

  method wb97xd and 6-311++g(d,p) as basis set was implemented to investigate the reaction products energetics parameters. The atomic charges were calculated and discussed in details using three different methods. The transition state search were implemented to estimate the Gibbs free activation energy barrier of the reaction to emphasis the experimental results.

  摘要 3-thioxo-1,2,4-triazin-5-ones 1 和 4-amino-3-mercapto-1,2,4-triazin-5(4H)-ones 2 作为新型结构单元的合成效用双和聚（1,2,4-三嗪）通过烷基化与相应的双和聚（卤）化合物进行了研究。已经使用光谱数据证实了烷基化位点的预测。使用混合密度泛函方法 wb97xd 和 6-311++g(d,p) 作为基础进行理论计算，以研究反应产物的能量参数。使用三种不同的方法计算和详细讨论了原子电荷。实施过渡态搜索以估计反应的吉布斯自由激活能垒，以强调实验结果。
• Synthesis, characterization, and fluorescence behavior of four novel macrocyclic emissive ligands containing a flexible 8-hydroxyquinoline unit
  作者：Cristina Núñez、Rufina Bastida、Alejandro Macías、Emilia Bértolo、Luz Fernandes、José Luis Capelo、Carlos Lodeiro

  DOI：10.1016/j.tet.2009.05.046

  日期：2009.8

  Four emissive macrocyclic ligands mono-substituted with an 8-hydroxyquinoline pendant arm are presented. The new compounds have been used for metal-ion detection, which results from the competition between PET (photo-induced electron transfer) and PPT (photo-induced proton transfer) mechanisms. Solid metal complexes with divalent Cu(II), Zn(II), and Cd(II), and trivalent metal ions Al(III) and Cr(III)

  提出了用8-羟基喹啉侧链单取代的四个发光大环配体。这些新化合物已用于金属离子检测，这是由于PET（光诱导电子转移）和PPT（光诱导质子转移）机理之间的竞争而产生的。还合成并表征了具有二价Cu（II），Zn（II）和Cd（II）以及三价金属离子Al（III）和Cr（III）的固体金属配合物。化合物已分离为单核或双核（Cu（II））配合物，证实了溶液中观察到的化学计量。
• Macrocyclic ligand design. Structure–function relationships involving the interaction of pyridinyl-containing, mixed oxygen–nitrogen donor macrocycles with cobalt(ii), nickel(ii), copper(ii), zinc(ii), cadmium(ii), silver(i) and lead(ii)
  作者：Ronald R. Fenton、Robert Gauci、Peter C. Junk、Leonard F. Lindoy、Robert C. Luckay、George V. Meehan、Jason R. Price、Peter Turner、Gang Wei

  DOI：10.1039/b201195f

  日期：2002.5.13

  A comparative investigation of the interaction of three dibenzo-substituted, mixed oxygen–nitrogen donor macrocycles with cobalt(II), nickel(II), copper(II), zinc(II), cadmium(II), silver(I) and lead(II) has been carried out. The thermodynamic stabilities of the respective complexes in 95% methanol (I = 0.1; Et4NClO4, 25 °C) have been determined. All ligands form 1 ∶ 1 (metal ∶ ligand) species with

  三种二苯并取代的混合氧相互作用的比较研究氮 捐赠者 大环用钴（II），镍（II），铜（II），锌（II），镉（II），银（I）和铅（II）进行了处理。各个配合物的热力学稳定性为95％甲醇（我 = 0.1;的Et 4 NClO 4，25°C）已被确定。全部配体 形式1：1（金属： 配体）具有上述金属离子的物质。将结果与先前从相关混合施主（循环）系统获得的结果进行比较。这些20元环的六个金属配合物的单晶结构配体 由...决定 X射线衍射。所有的大环供体位点都与铜（II）和镉（II）配合物中的金属离子结合。铜配合物为六坐标，而镉配合物为八坐标，并添加了双齿硝酸根离子。与银（I）络合形成三核络合物，其中两个含银大环 通过桥接的两个坐标链接 银离子。钴（II），镍（II）和锌（II）配合物中的每个金属原子都是六配位的，但是它们与大循环 仅在三个 仲胺 氮网站。配位球是由锌（II）络合物中的两个硝酸根