N',N''',N'''''-tri(naphthalen-1-yl)-N,N'',N''''-(nitrilotriethane-2,1-diyl)tris[urea]

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N',N''',N'''''-tri(naphthalen-1-yl)-N,N'',N''''-(nitrilotriethane-2,1-diyl)tris[urea]
• 英文别名: 1-[2-[Bis[2-(naphthalen-1-ylcarbamoylamino)ethyl]amino]ethyl]-3-naphthalen-1-ylurea；1-[2-[bis[2-(naphthalen-1-ylcarbamoylamino)ethyl]amino]ethyl]-3-naphthalen-1-ylurea
• 化学式: C₃₉H₃₉N₇O₃
• 分子量: 653.784
• InChiKey: UJEVFDOVVWOQEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  127
• 氢给体数：
  6
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  四丁基氯化铵 、 N',N''',N'''''-tri(naphthalen-1-yl)-N,N'',N''''-(nitrilotriethane-2,1-diyl)tris[urea] 在 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到
  参考文献：
  名称：

  被卤化物包裹的六聚体中性受体核心困住的冰状循环水六聚体：束缚在受体-阴离子胶囊组件中的水团簇的第一个晶体学证据

  摘要：

  在过去的几十年中，tren [三（2-氨基乙基）胺]骨架已经成为最高阴离子结合的结构单元之一，显示出拓扑结构，互补性，协同性和协调性之间的强大相互作用。然而，由于适度的基于tren的未取代芳族脲对阴离子的识别尚未得到充分的研究，这主要是由于缺乏π-酸性或吸电子的芳基末端。该报告建立了不常见的六聚体中性受体-阴离子-水分子自组装体，其中构象柔性的C 3 v-对称卤化物（F – / Cl –）包含N桥三脚架尿素受体的封装的富含电子的萘基，可以有效地将椅子状的冰状中性环状水六聚体截留在中性受体-卤化物主体-客体组合的六聚体腔内。

  DOI：

  10.1021/acs.cgd.7b01693
• 作为产物：
  描述：

  三(2-氨基乙基)胺 、 1-Alapha-萘异氰酸酯 以 乙腈 为溶剂， 以84%的产率得到N',N''',N'''''-tri(naphthalen-1-yl)-N,N'',N''''-(nitrilotriethane-2,1-diyl)tris[urea]
  参考文献：
  名称：

  被卤化物包裹的六聚体中性受体核心困住的冰状循环水六聚体：束缚在受体-阴离子胶囊组件中的水团簇的第一个晶体学证据

  摘要：

  在过去的几十年中，tren [三（2-氨基乙基）胺]骨架已经成为最高阴离子结合的结构单元之一，显示出拓扑结构，互补性，协同性和协调性之间的强大相互作用。然而，由于适度的基于tren的未取代芳族脲对阴离子的识别尚未得到充分的研究，这主要是由于缺乏π-酸性或吸电子的芳基末端。该报告建立了不常见的六聚体中性受体-阴离子-水分子自组装体，其中构象柔性的C 3 v-对称卤化物（F – / Cl –）包含N桥三脚架尿素受体的封装的富含电子的萘基，可以有效地将椅子状的冰状中性环状水六聚体截留在中性受体-卤化物主体-客体组合的六聚体腔内。

  DOI：

  10.1021/acs.cgd.7b01693

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.
• Ice-like Cyclic Water Hexamer Trapped within a Halide Encapsulated Hexameric Neutral Receptor Core: First Crystallographic Evidence of a Water Cluster Confined within a Receptor-Anion Capsular Assembly
  作者：Utsab Manna、Senjuti Halder、Gopal Das

  DOI：10.1021/acs.cgd.7b01693

  日期：2018.3.7

  Over the past few decades, the tren [tris(2-aminoethyl)amine] skeleton has materialized as one of the supreme anion binding building blocks demonstrating a strong interplay among topology, complementarity, cooperativity, and coordination. However, anion recognition by modest tren-based unsubstituted aromatic urea has been underexplored, mainly due to the deficiency of π-acidic or electron-withdrawing

  在过去的几十年中，tren [三（2-氨基乙基）胺]骨架已经成为最高阴离子结合的结构单元之一，显示出拓扑结构，互补性，协同性和协调性之间的强大相互作用。然而，由于适度的基于tren的未取代芳族脲对阴离子的识别尚未得到充分的研究，这主要是由于缺乏π-酸性或吸电子的芳基末端。该报告建立了不常见的六聚体中性受体-阴离子-水分子自组装体，其中构象柔性的C 3 v-对称卤化物（F – / Cl –）包含N桥三脚架尿素受体的封装的富含电子的萘基，可以有效地将椅子状的冰状中性环状水六聚体截留在中性受体-卤化物主体-客体组合的六聚体腔内。