2-[14,20-Bis(carboxymethyl)-12,22-dioxo-6,28-dioxa-11,14,17,20,23-pentazapentacyclo[27.2.2.22,5.27,10.224,27]nonatriaconta-1(32),2(39),3,5(38),7,9,24(35),25,27(34),29(33),30,36-dodecaen-17-yl]acetic acid | 1364601-70-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[14,20-Bis(carboxymethyl)-12,22-dioxo-6,28-dioxa-11,14,17,20,23-pentazapentacyclo[27.2.2.22,5.27,10.224,27]nonatriaconta-1(32),2(39),3,5(38),7,9,24(35),25,27(34),29(33),30,36-dodecaen-17-yl]acetic acid
• 英文别名: 2-[14,20-bis(carboxymethyl)-12,22-dioxo-6,28-dioxa-11,14,17,20,23-pentazapentacyclo[27.2.2.22,5.27,10.224,27]nonatriaconta-1(32),2(39),3,5(38),7,9,24(35),25,27(34),29(33),30,36-dodecaen-17-yl]acetic acid
• CAS: 1364601-70-6
• 化学式: C₃₈H₃₉N₅O₁₀
• 分子量: 725.755
• InChiKey: ATVHTGQOYJJKRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  53
• 可旋转键数：
  6
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  198
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  二亚乙基三胺五乙酸二酐 、 4,4'-二(4―氨基苯氧基)联苯 以 N,N-二甲基甲酰胺 为溶剂， 以33%的产率得到2-[14,20-Bis(carboxymethyl)-12,22-dioxo-6,28-dioxa-11,14,17,20,23-pentazapentacyclo[27.2.2.22,5.27,10.224,27]nonatriaconta-1(32),2(39),3,5(38),7,9,24(35),25,27(34),29(33),30,36-dodecaen-17-yl]acetic acid
  参考文献：
  名称：

  Fluorescent aza-cyclophanes derived from diethylenetriaminepentaacetic acid (DTPA), and their complexation with Gd(III)

  摘要：

  Chelating aza-cyclophanes were synthesized by reactions of diethylenetriaminepentaacetic acid (or DTPA) dianhydride with aromatic diamines, 4,4'-diaminobibenzyl (DAB) and 4,4'-bis(1,1'-biphenyl-4,4'-diyldioxy)dianiline (BPA). The former amine gave a 2:2-cyclization product bearing six -CH2CO2H arms, 2,12,29,39-tetraoxo-4,7,10,31,34,37-hexakis(carboxymethylene)-1,4,7,10,13,28,31,34,37,40-decaaza-[13.2.13.2]ethylenparacyclophane, abbreviated as cy(bisdtpadab)H-6, whereas BPA yielded a 1:1-cyclization product carrying three -CH2CO2H arms, 2,12-dioxo-4,7,10-trakis(carboxymethylene)1,4,7,10,13-pentaaza-20,33-dioxa[13.0.1]paracyclophane, abbreviated as cy(dtpabpa)H-3. Their protonation and complexation with Gd(III) were studied by fluorescence spectra, H-1 NMR and potentiometry. The macrocyclic framework of cy(dtpabpa)H-3 has a high rigidity: as a consequence, this ligand is incapable of forming a complex with Gd(III). In contrast, cy(bisdtpadab)H-6, which is moderately rigid, forms a binuclear Gd(III) complex, as confirmed by a sensitive quenching of the fluorescence upon complexation. On the basis of the pH dependence of the fluorescence spectra, the logarithmic overall formation constants were determined as log beta(M2L) = 28.3, log beta(M2LH) = 31.9, log beta(M2LH-1)= 21.0, log beta(M2LH-2) = 9.8. For the chelating cyclophanes, the rigidity is one of major controlling factors for the stability of their complexes. The sharp change in the fluorescence intensity upon complexation with Gd3+ ion suggests that the chelating cyclophane works potentially as fluorescent probes toward specific metal ions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.01.007