1-{4-[bis(2-methoxyethyl)amino]phenyl}-3-(4-nitrophenyl)urea | 1186076-87-8

• 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: 1-{4-[bis(2-methoxyethyl)amino]phenyl}-3-(4-nitrophenyl)urea
• 英文别名: 1-[4-[Bis(2-methoxyethyl)amino]phenyl]-3-(4-nitrophenyl)urea
• CAS: 1186076-87-8
• 化学式: C₁₉H₂₄N₄O₅
• 分子量: 388.423
• InChiKey: IANPRBGCRXZGIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N,N-bis(2-methoxyethyl)benzene-1,4-diamine 、 异氰酸对硝基苯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到1-{4-[bis(2-methoxyethyl)amino]phenyl}-3-(4-nitrophenyl)urea
  参考文献：
  名称：

  “Wurster-Type” Ureas as Redox-Active Receptors for Anions

  摘要：

  Four redox-active receptors, 1-4, based on the incorporation of p-phenylenediamine(s) within a urea framework, were synthesized, and the affinities of two for a series of anions were quantified through UV-vis and NMR spectroscopic studies. The structure of 1 was confirmed by X-ray crystallography. For the oxoanions studied, complex stabilities approached 10(6) M-1 in acetonitrile and decreased with the decreasing basicity of the anion (CH3COO- > C6H5COO- > H2PO4- > NO2- > NO3-). The presence of the urea functionality caused an increase in the oxidation potential of the p-phenylenediamine subunit compared to that of free p-phenylenediamine. Electrochemical studies of the anion complexes revealed two-wave behavior with the appearance of a second oxidation wave cathodic to that in the free receptors and characteristic of the bound anion, Ab initio DFT studies of a representative acetate complex revealed the consequences of host oxidation state on complex structure.

  DOI：

  10.1021/jo9011392

文献信息

• “Wurster-Type” Ureas as Redox-Active Receptors for Anions
  作者：John P. Clare、Anna Statnikov、Vincent Lynch、Andrew L. Sargent、John W. Sibert

  DOI：10.1021/jo9011392

  日期：2009.9.4

  Four redox-active receptors, 1-4, based on the incorporation of p-phenylenediamine(s) within a urea framework, were synthesized, and the affinities of two for a series of anions were quantified through UV-vis and NMR spectroscopic studies. The structure of 1 was confirmed by X-ray crystallography. For the oxoanions studied, complex stabilities approached 10(6) M-1 in acetonitrile and decreased with the decreasing basicity of the anion (CH3COO- > C6H5COO- > H2PO4- > NO2- > NO3-). The presence of the urea functionality caused an increase in the oxidation potential of the p-phenylenediamine subunit compared to that of free p-phenylenediamine. Electrochemical studies of the anion complexes revealed two-wave behavior with the appearance of a second oxidation wave cathodic to that in the free receptors and characteristic of the bound anion, Ab initio DFT studies of a representative acetate complex revealed the consequences of host oxidation state on complex structure.