4'-hydroxy-5'-formyl-benzo-15-crown-5 | 154615-42-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-hydroxy-5'-formyl-benzo-15-crown-5
• 英文别名: 4'-hydroxy-5'-formylbenzo-18-crown-6 ether；21-Hydroxy-2,5,8,11,14,17-hexaoxabicyclo[16.4.0]docosa-1(18),19,21-triene-20-carbaldehyde
• CAS: 154615-42-6
• 化学式: C₁₇H₂₄O₈
• 分子量: 356.373
• InChiKey: FZEAQMAHHPLRDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4'-hydroxy-5'-formyl-benzo-15-crown-5 在 哌啶 、 tetra-N-butylammonium tribromide 、 potassium hydrogencarbonate 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 14.17h， 生成 Dodecanoic acid 2-oxo-2-(22-oxo-2,5,8,11,14,17,21-heptaoxa-tricyclo[16.8.0.0^20,25]hexacosa-1(18),19,23,25-tetraen-23-yl)-ethyl ester
  参考文献：
  名称：

  Synthesis and Evaluation of Novel Crowned Coumarins as Self-Catalytic Fluorescence Reagents

  摘要：

  设计并合成了三种具有冠醚部分作为荧光衍生化羧酸的催化位点的香豆素试剂。根据与金属醋酸盐在甲醇中的配位稳定常数（Ks）评估了这些试剂的催化能力。这些试剂与羧酸的衍生化反应是在没有冠醚催化剂的情况下自催化进行的，并且可以获得相应的香豆素酯，其产率良好。研究发现，反应的反应性显著依赖于试剂分子的金属结合能力，反应的动力学处理证实了这一点。衍生化产品在甲醇中显示出超过0.8的显著高荧光量子产率。这些结果表明，试剂的功能化是开发新型分析试剂的一个非常有用的方法。

  DOI：

  10.1246/bcsj.68.3105
• 作为产物：
  描述：

  2,4,5-三羟基苯甲醛 、 1,14-diiodo-3,6,9,12-tetraoxatetradecane 在 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 65.0h， 生成 4'-hydroxy-5'-formyl-benzo-15-crown-5
  参考文献：
  名称：

  3-芳基香豆素冠醚的合成和络合特性。一类新的光敏大环化合物。

  摘要：

  描述了由3-苯甲酰基香豆素与冠醚稠合的氟离子载体在两种不同模式下的合成。所得的大环化合物的发射性质强烈依赖于金属离子和香豆素的取代，因此可以用作依赖阳离子的荧光信号系统或镧系元素发光的三重态敏化剂。

  DOI：

  10.1016/s0040-4039(00)60154-5

文献信息

• Synthesis and characterization of unsymmetrically tetrasubstituted porphyrin and their nickel (II) complexes with the crystal structure of 5,15-bis(4-aminophenyl)-10, 20-diphenylporphyrinatonickel(II)
  作者：M. Hayvalı、H. Gündüz、N. Gündüz、Z. Kılıç、T. Hökelek

  DOI：10.1016/s0022-2860(00)00417-8

  日期：2000.7

  New unsymmetrically tetrasubstituted porphyrin-Schiff base ligands (8-10) containing recognition sites for alkali and transition metal quest cations have been synthesized by the condensations of 5-(4-aminophenyl)-10,15,20- triphenylporphyrin (5) with salycylaldehyde, 2-hydroxy-1-naphthaldehyde and 4'-hydroxy-5'-formyl-benzo-15-crown-5. Homonuclear crystalline 1:1 [Ni(II): ligand] complexes (8a-10a) of the ligands with Ni(CH2COO)(2). 4H(2)O have been obtained. The porphyrin ligands and their complexes have been characterized by elemental analysis, IR, UV-VIS, H-1, C-13 NMR and MS, and the structure of trans-5,15-bis(4-aminophenyl)-10,20-diphenylporphyrinato-nickel(II) (7a) has been examined crystallographically. It crystallizes in the monoclinic space group C2/c with a = 22.096(2), b = 13.455(1), c = 15.599(1) Angstrom, beta = 134.81(1)degrees, V = 3290.6(2) Angstrom(3), Z = 4 and D-x = 1.42 g cm(-3). The molecule is centrosymmetric and the porphine nucleus is non-planar. The average value for the diameter of the hole has been estimated as 3.830(4) Angstrom. (C) 2000 Elsevier Science B.V. All rights reserved.
• Supramolecular assemblies of crown-substituted dinickel and dicobalt complexes with guest cation binding
  作者：Hisashi Shimakoshi、Daisuke Maeda、Yoshio Hisaeda

  DOI：10.1080/10610278.2010.514910

  日期：2011.1.1

  A new macrocyclic ligand (L1) having four crown ether moieties at the peripheral position was synthesised by a conventional Schiff-base condensation reaction. The corresponding dinickel (1) and dicobalt (2) complexes formed a unique face-to-face dimerised structure by complexation with a Cs+ ion, which was characterised by 1H NMR, UV-vis and electrospray ionisation (ESI)-MS. Multi-sandwich structures consist of a 2:1 interaction of the benzo-18-crown-6 ether with the Cs+ ion affording a significantly high overall formation constant (Kall=25.9 +/- 0.9 at 298K). The redox behaviour of the assembled structure of the dicobalt complex was investigated by cyclic voltammetry. In the dimerised structure, two sequential reductions ascribed to the CoIICoII/CoIICoI and CoIICoI/CoICoI couples were observed at -1.13V (E1) and -1.36V (E2) vs. Ag/AgCl, and both potentials were separated by E=E1-E2=0.23V. A mixed valence state (CoIICoI) was stabilised in the complex with the comproportionation constant Kcom=7.7x103 at 298K.