N',N''',N'''''-tris(3-phenylpropyl)-N,N'',N''''-(nitrilotriethan-2,1-diyl)tris[urea]

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N',N''',N'''''-tris(3-phenylpropyl)-N,N'',N''''-(nitrilotriethan-2,1-diyl)tris[urea]
• 英文别名: 1-[2-[Bis[2-(3-phenylpropylcarbamoylamino)ethyl]amino]ethyl]-3-(3-phenylpropyl)urea；1-[2-[bis[2-(3-phenylpropylcarbamoylamino)ethyl]amino]ethyl]-3-(3-phenylpropyl)urea
• 化学式: C₃₆H₅₁N₇O₃
• 分子量: 629.846
• InChiKey: BKOYCSZPDAITPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  46
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  127
• 氢给体数：
  6
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三(3-氨基丙基)胺 、 3-苯丙基异氰酸酯 以 甲苯 为溶剂， 以1.76 g的产率得到N',N''',N'''''-tris(3-phenylpropyl)-N,N'',N''''-(nitrilotriethan-2,1-diyl)tris[urea]
  参考文献：
  名称：

  Complexation of Anions Including Nucleotide Anions by Open-Chain Host Compounds with Amide, Urea, and Aryl Functions

  摘要：

  A systematical evaluation of association constants between halide, phosphate, and carboxylate anions with N-methylformamide (1) and the related bidentate receptors 2-6 (derived from, e.g., phthalic acid or ethylenediamine) in CDCl3 as solvent yielded increments of complexation free-energy Delta Delta G for each single H-bond, which varied like, e.g., 5.1 kJ/mol (for Cl-), 4.0 kJ/mol (for Br-), 4.0 kJ/mol (for I-) (with values taken from Tables 1 and 2), in line with expected H-bond strength. The observed complexation induced NH-NMR shift (CIS) values also showed a regular change, in the case of 1 e.g., from 5.0 to 2.8 to 2.1 ppm (Table 1), with about half of these values with the bidentate ligands (Tables 2 and 3). Tridentate hosts led to a substantial binding increase, if strain-free convergence of all NH donor functions towards the anion was possible. The tris[urea] ligand 10 yielded, even in the polar solvent DMSO, with Cl- a Delta G of - 21.5 kJ/mol and with Br- of - 10.5 kJ/mol, whereas with I-, no association was detectable. The results demonstrated that small, inexpensive, and conformationally mobile host compounds can exhibit high affinities as well as descrimination with anions, as much as more preorganized receptors do which require multistep synthesis. The corresponding adamantyl derivative 13 allowed measurements also in CDCl3, with K = 4.3 . 10(4) M-1 for chloride (Table 7). Complexes with nucleotide anions were again particularly strong with the tridentate urea-based ligands, the latter being optimal ligands for chloride complexation. For the association of 10 with AMP(2-) and GMP(2-)in (D-6)DMSO, the association constants were 3 . 10(4) M-1 (Table 8) and almost the: same as with Cl-. In the case of the urea derivatives 17 18, and 21, containing only one phenyl or pyrenyl substituent, however, the Delta G values decreased in the order A > C > T > G (e.g. - 13.6, - 11.6, - 7.6, - 10.5 kJ/mol in the case of 17 resp.; Table 8). In H2O, the pyrenyl-substituted urea derivatives allow measurements with fluorescence, and, unexpectedly show only smaller nucleobase discrimination, with constants around 3 . 10(3) M-1.

  DOI：

  10.1002/(sici)1522-2675(20000216)83:2<465::aid-hlca465>3.0.co;2-f

文献信息

• Complexation of Anions Including Nucleotide Anions by Open-Chain Host Compounds with Amide, Urea, and Aryl Functions
  作者：Frank Werner、Hans-Jörg Schneider

  DOI：10.1002/(sici)1522-2675(20000216)83:2<465::aid-hlca465>3.0.co;2-f

  日期：2000.2.16

  A systematical evaluation of association constants between halide, phosphate, and carboxylate anions with N-methylformamide (1) and the related bidentate receptors 2-6 (derived from, e.g., phthalic acid or ethylenediamine) in CDCl3 as solvent yielded increments of complexation free-energy Delta Delta G for each single H-bond, which varied like, e.g., 5.1 kJ/mol (for Cl-), 4.0 kJ/mol (for Br-), 4.0 kJ/mol (for I-) (with values taken from Tables 1 and 2), in line with expected H-bond strength. The observed complexation induced NH-NMR shift (CIS) values also showed a regular change, in the case of 1 e.g., from 5.0 to 2.8 to 2.1 ppm (Table 1), with about half of these values with the bidentate ligands (Tables 2 and 3). Tridentate hosts led to a substantial binding increase, if strain-free convergence of all NH donor functions towards the anion was possible. The tris[urea] ligand 10 yielded, even in the polar solvent DMSO, with Cl- a Delta G of - 21.5 kJ/mol and with Br- of - 10.5 kJ/mol, whereas with I-, no association was detectable. The results demonstrated that small, inexpensive, and conformationally mobile host compounds can exhibit high affinities as well as descrimination with anions, as much as more preorganized receptors do which require multistep synthesis. The corresponding adamantyl derivative 13 allowed measurements also in CDCl3, with K = 4.3 . 10(4) M-1 for chloride (Table 7). Complexes with nucleotide anions were again particularly strong with the tridentate urea-based ligands, the latter being optimal ligands for chloride complexation. For the association of 10 with AMP(2-) and GMP(2-)in (D-6)DMSO, the association constants were 3 . 10(4) M-1 (Table 8) and almost the: same as with Cl-. In the case of the urea derivatives 17 18, and 21, containing only one phenyl or pyrenyl substituent, however, the Delta G values decreased in the order A > C > T > G (e.g. - 13.6, - 11.6, - 7.6, - 10.5 kJ/mol in the case of 17 resp.; Table 8). In H2O, the pyrenyl-substituted urea derivatives allow measurements with fluorescence, and, unexpectedly show only smaller nucleobase discrimination, with constants around 3 . 10(3) M-1.