tris-{{2-benzaldehyde}-oxoethyl}-amine | 146253-69-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tris-{{2-benzaldehyde}-oxoethyl}-amine
• 英文别名: tris{[2-(2'-(oxomethyl)phenyl)oxy]ethyl}amine；2,2',2''-((nitrilotris(ethane-2,1-diyl))tris(oxy))tribenzaldehyde；tri[2-(2-formylphenoxy)ethyl]amine；2-[2-[Bis[2-(2-formylphenoxy)ethyl]amino]ethoxy]benzaldehyde
• CAS: 146253-69-2
• 化学式: C₂₇H₂₇NO₆
• 分子量: 461.514
• InChiKey: BHAFRTGNAVSNAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tris-{{2-benzaldehyde}-oxoethyl}-amine 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 N-[[2-[2-[bis[2-[2-[(1H-benzimidazol-2-ylamino)methyl]phenoxy]ethyl]amino]ethoxy]phenyl]methyl]-1H-benzimidazol-2-amine
  参考文献：
  名称：

  Benzimidazole-Based Tripodal Receptor:  Highly Selective Fluorescent Chemosensor for Iodide in Aqueous Solution

  摘要：

  We synthesized a novel tripodal fluorescent receptor bearing benzimidazole motifs as recognition sites in the pods of the receptor. The recognition behavior of the receptor toward various anions was evaluated in CH3CN/H2O (9:1, v/v) solution. The receptor showed changes in fluorescent intensity only with I-, but it showed no significant changes on addition of other anions such as F-, Cl-, Br-, HSO4-, NO3-, CH3COO-, and H2PO4-.

  DOI：

  10.1021/ol070592r
• 作为产物：
  描述：

  三(2-氯乙基)胺 、 水杨醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以48%的产率得到tris-{{2-benzaldehyde}-oxoethyl}-amine
  参考文献：
  名称：

  用于感测多种分析物单化学传感器：选择性荧光检测的Cu 2+和Br -

  摘要：

  设计了具有氮和氧基结合位点的三脚架受体R1，并将其用于选择性测定Cu 2+。在存在Cu 2+的情况下，R1的荧光发射曲线显示荧光强度显着增强，表明在其他金属离子中具有较高的选择性。所述R1 -Cu 2+复合物进一步探讨作为阴离子检测的传感器。在添加的Br - ，观察切换到荧光“关”状态。该溴-通过在发光光谱的变化通过滴定分析中观察到的复合物在宽浓度范围内的选择性。

  DOI：

  10.1016/j.tetlet.2018.09.024

文献信息

• Synthesis of cryptands having tritopic receptor sites by [2+3] Schiff base condensation using Cs(I) ion as the template
  作者：Kaliappa G. Ragunathan、Rameshwer Shukla、Swati Mishra、Parimal K. Bharadwaj

  DOI：10.1016/s0040-4039(00)73901-3

  日期：1993.8

  Synthesis of two tritopic receptors L1 and L2 by [2+3] Schiff base condensation of trialdehyde 1 or 2 and 1,2-diaminobenzene followed by reduction with NaBH4 are reported. The reactions undergo smoothly in presence of Cs(I) ion as the template.

  据报道，通过[2 + 3]三醛1或2与1,2-二氨基苯的席夫碱缩合，然后用NaBH 4还原，可以合成两个三位受体L 1和L 2。在以Cs（I）离子为模板的情况下，反应平稳进行。
• Complexation properties of a heteroditopic cryptand towards CuII and NiII, crystal structures of the cryptand and its nickel(II) cascade complex
  作者：Pradyut Ghosh、Sayam Sen Gupta、Parimal K. Bharadwaj

  DOI：10.1039/a605948a

  日期：——

  The crystal structure of the heteroditopic cryptand (L) formed by Schiff-base condensation of tris(2-aminoethyl)amine and 2,2′,2″-nitrilotris(ethyleneoxy)tris(benzaldehyde) followed by reduction with NaBH 4 has been determined. The molecule has an endo-endo conformation with a pseudo-three-fold symmetry axis passing through the two bridgehead nitrogens. This symmetry is maintained in chloroform solution as indicated by its 1 H NMR spectrum. The cryptand accepts a metal ion (Cu II , Zn II or Ni II ) inside the cavity forming mononuclear cryptates of general formula [ML][ClO 4 ] 2 . The metal ion occupies the N 4 end of the cavity. The light blue CuN 4 chromophore thus formed exhibits an axial EPR spectrum with very small A ∥ value (63 × 10 -4 cm -1 ) and a low-energy ligand-field band. Nickel(II) initially forms a blue [NiL][ClO 4 ] 2 complex which on dissolving in moist MeCN solution crystallizes as purple rectangular parallelopipeds with the formulation [NiL(H 2 O)(MeCN)][ClO 4 ] 2 ·H 2 O·2MeCN. The crystal structure of this complex has also been determined. The Ni II ion is octahedrally co-ordinated with the equatorial sites occupied by the three secondary amino N atoms of the cryptand and the N atom of the bound MeCN. The axial sites are occupied by the bridgehead N and the O atom of the water molecule which enters the cavity forming a cascade complex.

  通过Schiff-base缩合反应形成的异双齿穴醚(L)的晶体结构，由三(2-氨基乙基)胺和2,2′,2″-氮三(乙烯氧基)三(苯甲醛)组成，随后用NaBH4还原，已被确定。该分子具有endo-endo构型，通过两个桥头氮原子存在一个伪三重对称轴。这种对称性在氯仿溶液中得到保持，如1H NMR谱所示。该穴醚在腔内接受金属离子(Cu II、Zn II或Ni II)，形成通式为[ML][ClO4]2的单核穴合物。金属离子占据腔内N4端。形成的CuN4光蓝色素表现出轴向EPR谱，具有非常小的A∥值(63 × 10-4 cm-1)和低能量配体场带。镍(II)最初形成蓝色的[NiL][ClO4]2配合物，在湿润的MeCN溶液中溶解后结晶为紫色矩形平行六面体，具有配方[NiL(H2O)(MeCN)][ClO4]2· ·2MeCN。该配合物的晶体结构也已被确定。Ni II离子是八面体配位的，赤道位点由穴醚的三个二级氨基N原子和结合的MeCN的N原子占据。轴向位点由桥头N和进入腔内的水分子形成瀑布型配合物的O原子占据。
• Synthesis, characterization and complexation properties of a heteroditopic cryptand L towards CuII and ZnII: crystal structures of L·3H2O and [ZnL][ClO4]2·2H2O
  作者：Pradyut Ghosh、Parimal K. Bharadwaj

  DOI：10.1039/a701692a

  日期：——

  A new heteroditopic cryptand (L) has been synthesized in high yields, at 5 °C and in absence of any templating metal ion, by tripod–tripod Schiff-base condensation of tris(3-aminopropyl)amine and 2,2′,2″-nitrilotris(ethyleneoxy)tris(benzaldehyde) followed by reduction in situ with NaBH 4 . The molecule has an endo-endo conformation with a distance of 5.291 Å between the two bridgehead nitrogens. The cryptand forms mononuclear cryptates of the general formula [ML][ClO 4 ] 2 with copper(II) and zinc(II) perchlorates. The crystal structure of [ZnL][ClO 4 ] 2 ·2H 2 O was determined. The Zn II occupies the N 4 end of the cavity in an almost ideal tetrahedral geometry. The blue copper(II) cryptate exhibits ligand-field bands at 875 and 745 nm and a ligand-to-metal charge transfer at 275 nm in acetonitrile solution at 298 K indicative of pseudo-tetrahedral CuN 4 co-ordination. However, its EPR spectral characteristics in the solid state or in solution are typical of a magnetically concentrated complex.

  通过三(3-氨基丙基)胺和 2,2′,2″-硝基三(乙烯氧基)三(苯甲醛)的三脚架-三脚架席夫碱缩合，然后用 NaBH 4 原位还原，在 5 ℃ 和无任何模板金属离子的条件下，高产率地合成了一种新的杂二价隐核糖（L）。分子具有内端构象，两个桥头硝基之间的距离为 5.291 Å。这种隐核糖与铜（II）和锌（II）高氯酸盐形成通式为 [ML][ClO 4 ] 2 的单核隐核酸盐。测定了 [ZnL][ClO 4 ] 2 -2H 2 O 的晶体结构。Zn II 以几乎理想的四面体几何形状占据了空腔的 N 4 端。在 298 K 的乙腈溶液中，蓝色的隐色酸铜（II）在 875 和 745 纳米波长处显示出配位体场带，在 275 纳米波长处显示出配位体对金属的电荷转移，这表明存在假四面体 CuN 4 配位。不过，它在固态或溶液中的 EPR 光谱特征是典型的磁浓缩复合物。
• Novel Hydrazone-Based Tripodal Sensors: Single Selective Colorimetric Chemosensor for Acetate in Aqueous Solution
  作者：Youming Zhang、Qiao Li、Qinsheng Zhang、Qi Lin、Cheng Cao、Mingxia Liu、Taibao Wei

  DOI：10.1002/cjoc.201180275

  日期：2011.7

  series of novel tripodal colorimetric anion sensors based on hydrazone CHNNH groups have been synthesized and their recognition behavior with anionic guests has been studied. In DMSO solutions, sensors 1 and 2 show colorimetric responses for F−, H2PO−4 and AcO−, while in DMSO/H2O (9:1, V/V) solutions, sensor 1 shows single selectivity for AcO−. 1H NMR titration confirms that the tripodal sensors could

  一系列基于腙CHN新颖三足比色阴离子传感器 NH基团已被合成并与阴离子客人它们的识别的行为进行了研究。在DMSO溶液，传感器1和2示出适用于F比色反应-，H 2 PO - 4和ACO - ，而在DMSO / H 2 O（9：1，V / V）溶液，传感器1只示出了单个用于ACO选择性-。1个1 H NMR滴定证实三脚架传感器可以通过三个基团和驻留在传感器中心腔中的阴离子的结合而结合阴离子。
• Toward dynamic combinatorial libraries of cryptands
  作者：Krzysztof Ziach、Magdalena Ceborska、Janusz Jurczak

  DOI：10.1016/j.tetlet.2011.06.075

  日期：2011.8

  The first examples of dynamic combinatorial libraries of cryptands, created using the chemistry of imines is presented. Experiments, in which two trialdehydes compete for one triamine in a small library, show the full reversibility of cryptand formation, since the library composition is the same irrespective of the sequence of introducing the building blocks to the mixture. (C) 2011 Published by Elsevier Ltd.