1,1'-(propane-1,3-diyl)-bis[3-(naphthalen-2-yl)urea] | 1309655-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,1'-(propane-1,3-diyl)-bis[3-(naphthalen-2-yl)urea]
• 英文别名: 1-Naphthalen-2-yl-3-[3-(naphthalen-2-ylcarbamoylamino)propyl]urea；1-naphthalen-2-yl-3-[3-(naphthalen-2-ylcarbamoylamino)propyl]urea
• CAS: 1309655-87-5
• 化学式: C₂₅H₂₄N₄O₂
• 分子量: 412.491
• InChiKey: VFGXQTQLXMKBEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  82.3
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1'-(propane-1,3-diyl)-bis[3-(naphthalen-2-yl)urea] 以 氘代二甲亚砜 为溶剂， 生成
  参考文献：
  名称：

  Phosphate selective alkylenebisurea receptors: structure-binding relationship

  摘要：

  New host molecules for anions, adamantane, and alkyl urea derivatives substituted by naphthalene chromophores, were synthesized. Their binding with F-, Cl-, Br-, OAc-, HSO4-, NO3-, and H2PO4- was investigated by UV-vis, fluorescence and NMR spectroscopy. The anion binding ability of adamantyl bisurea derivatives was compared with the analogous host molecules, wherein the urea moieties are separated by flexible alkyl linkers of the same length, and adamantane monourea derivative. The host molecules show the highest selectivity toward F- and H2PO4-. The binding stoichiometry and the values of the association constants depend on the basicity of anions, availability of H-bonding sites, preorganization, and rigidity of the hosts, as well as solvent polarity and H-bonding availability. Rigid adamantane receptors, compared to flexible analogues show increased selectivity for H2PO4-, whereas binding of OAc- is better with flexible receptors. The binding of OAc- and H2PO4- was investigated by microcalorimetry. The stoichiometries and the stability constants of the corresponding complexes obtained by this method were in good agreement compared to those determined by UV-vis titrations. In both cases the enthalpic contribution to the overall complex stability was predominant. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.096
• 作为产物：
  描述：

  1,3-丙二胺 、 2-萘基异氰酸酯 以 甲苯 为溶剂， 反应 16.0h， 以175 mg的产率得到1,1'-(propane-1,3-diyl)-bis[3-(naphthalen-2-yl)urea]
  参考文献：
  名称：

  Phosphate selective alkylenebisurea receptors: structure-binding relationship

  摘要：

  New host molecules for anions, adamantane, and alkyl urea derivatives substituted by naphthalene chromophores, were synthesized. Their binding with F-, Cl-, Br-, OAc-, HSO4-, NO3-, and H2PO4- was investigated by UV-vis, fluorescence and NMR spectroscopy. The anion binding ability of adamantyl bisurea derivatives was compared with the analogous host molecules, wherein the urea moieties are separated by flexible alkyl linkers of the same length, and adamantane monourea derivative. The host molecules show the highest selectivity toward F- and H2PO4-. The binding stoichiometry and the values of the association constants depend on the basicity of anions, availability of H-bonding sites, preorganization, and rigidity of the hosts, as well as solvent polarity and H-bonding availability. Rigid adamantane receptors, compared to flexible analogues show increased selectivity for H2PO4-, whereas binding of OAc- is better with flexible receptors. The binding of OAc- and H2PO4- was investigated by microcalorimetry. The stoichiometries and the stability constants of the corresponding complexes obtained by this method were in good agreement compared to those determined by UV-vis titrations. In both cases the enthalpic contribution to the overall complex stability was predominant. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.096

文献信息

• Phosphate selective alkylenebisurea receptors: structure-binding relationship
  作者：Vesna Blažek、Nikola Bregović、Kata Mlinarić-Majerski、Nikola Basarić

  DOI：10.1016/j.tet.2011.03.096

  日期：2011.5

  New host molecules for anions, adamantane, and alkyl urea derivatives substituted by naphthalene chromophores, were synthesized. Their binding with F-, Cl-, Br-, OAc-, HSO4-, NO3-, and H2PO4- was investigated by UV-vis, fluorescence and NMR spectroscopy. The anion binding ability of adamantyl bisurea derivatives was compared with the analogous host molecules, wherein the urea moieties are separated by flexible alkyl linkers of the same length, and adamantane monourea derivative. The host molecules show the highest selectivity toward F- and H2PO4-. The binding stoichiometry and the values of the association constants depend on the basicity of anions, availability of H-bonding sites, preorganization, and rigidity of the hosts, as well as solvent polarity and H-bonding availability. Rigid adamantane receptors, compared to flexible analogues show increased selectivity for H2PO4-, whereas binding of OAc- is better with flexible receptors. The binding of OAc- and H2PO4- was investigated by microcalorimetry. The stoichiometries and the stability constants of the corresponding complexes obtained by this method were in good agreement compared to those determined by UV-vis titrations. In both cases the enthalpic contribution to the overall complex stability was predominant. (C) 2011 Elsevier Ltd. All rights reserved.