1,1'-(adamantane-1,3-diyl)-bis[3-(naphthalen-2-yl)urea] | 1246887-92-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,1'-(adamantane-1,3-diyl)-bis[3-(naphthalen-2-yl)urea]
• 英文别名: 1-Naphthalen-2-yl-3-[3-(naphthalen-2-ylcarbamoylamino)-1-adamantyl]urea
• CAS: 1246887-92-2
• 化学式: C₃₂H₃₂N₄O₂
• 分子量: 504.632
• InChiKey: CHHCMZXTCCQQIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 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'-(adamantane-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-金刚烷二甲酸 在 二苯基膦叠氮化物 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 21.0h， 生成 1,1'-(adamantane-1,3-diyl)-bis[3-(naphthalen-2-yl)urea]
  参考文献：
  名称：

  萘-，蒽-和pyr基-金刚烷双脲衍生物聚集体的光物理研究

  摘要：

  Adamantaneurea衍生物1 - 13的合成和它们的光物理性质的影响。化合物1 - 13是由刚性的金刚烷部分的，1或2个脲基团和发色团的不同，以及金刚烷和脲之间和/或尿素和发色团之间的亚甲基间隔基。在CH 3 CN和DMSO中测量了荧光量子产率和单线激发态寿命。发现在金刚烷和尿素之间具有亚甲基间隔基的分子在CH 3 CN中聚集，而在DMSO中未观察到聚集。9-氨基蒽衍生物10的聚集趋势最高在两种溶剂中聚集的pyr衍生物13。由于脲之间的分子间氢键和芳族发色团的π，π堆积，可能发生聚集。芘13可能引起的准分子激光和分子间的聚集。

  DOI：

  10.1016/j.jphotochem.2011.12.005

文献信息

• Adamantane bisurea derivatives: anion binding in the solution and in the solid state
  作者：Vesna Blažek、Krešimir Molčanov、Kata Mlinarić-Majerski、Biserka Kojić-Prodić、Nikola Basarić

  DOI：10.1016/j.tet.2012.11.030

  日期：2013.1

  1,3-Bis-(3-arylureido)adamantane receptors, bearing phenyl (5,6), 1-naphthyl (7,8) and 9-anthryl (9) fluorophore, were synthesized. Their ability for complexation with F-, Cl-, Br-, OAc-, NO3-, HSO4-, and H2PO4- in solution was investigated by UV-vis and fluorescence spectrophotometry. The binding was compared to that of 2-naphthyl bisurea derivatives with flexible spacers (bearing propylene or pentalene, 2 and 4) and rigid adamantane analogues (1 and 3). In solution, the receptors form stable complexes with all anions except with NO3-. The complexation ability in CH3CN correlates with the basicity of anion and the acidity of the urea N-H, whereas in DMSO the complexes stability variations are less pronounced. The X-ray structure of receptor 1 indicates that incorporation of the adamantane moiety preorganizes the receptor in a tweezer-like conformation for the optimal formation of hydrogen bonding network and high selectivity for H2PO4- anion. Incorporation of the methylene spacers between the adamantane and the urea additionally increases stability of the complexes with anions. X-ray structural analysis was performed on the following complexes: 1 center dot Bu4NH2PO4, 3 center dot Bu4NH2PO4, 5 center dot Bu4NH2PO4 center dot 4H(2)O, and 5 center dot Bu4NOAc center dot 3H(2)O. All H2PO4- complexes include extensive receptor ... H2PO4- hydrogen bonds, essential for the anion recognition, as well as H2PO4- ... H2PO4- hydrogen bonds. (c) 2012 Elsevier Ltd. All rights reserved.
• [EN] ADAMANTANE BISUREA DERIVATIVES, METHOD OF PREPARATION AND APPLICATION IN ANION SENSING<br/>[FR] DÉRIVÉS D'ADAMANTANE-BISURÉE, PROCÉDÉ DE PRÉPARATION ET APPLICATION À LA DÉTECTION D'ANIONS
  申请人：RUDJER BOSKOVIC INST

  公开号：WO2010112946A1

  公开（公告）日：2010-10-07

  The invention relates to adamantane bisurea derivatives and their use. Adamantane bisurea derivatives are obtained by reaction of adamantane diamine with appropriate isocyanate, or by in situ preparation of adamantane isocyanate from adamantane diacid and subsequent reaction with the appropriate amine. Adamantane bisureas bind the following anions: F-, Cl-, Br-, acetate, HSO4- NO3-, and H2PO4-, and particularly F- and H2PO4-. The presence of anions can be detected by UV -vis or fluorescence spectroscopy. Formula (I).
• 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.
• Photophysical study of the aggregation of naphthyl-, anthryl- and pyrenyl-adamantanebisurea derivatives
  作者：Vesna Blažek、Kata Mlinarić-Majerski、Wenwu Qin、Nikola Basarić

  DOI：10.1016/j.jphotochem.2011.12.005

  日期：2012.2

  Adamantaneurea derivatives 1–13 were synthesized and their photophysical properties investigated. The compounds 1–13 are comprised of a rigid adamantane moiety, 1 or 2 urea groups and different chromophores, as well as methylene spacer between the adamantane and the urea and/or between the urea and the chromophores. Fluorescence quantum yields and singlet excited state lifetimes were measured in CH3CN

  Adamantaneurea衍生物1 - 13的合成和它们的光物理性质的影响。化合物1 - 13是由刚性的金刚烷部分的，1或2个脲基团和发色团的不同，以及金刚烷和脲之间和/或尿素和发色团之间的亚甲基间隔基。在CH 3 CN和DMSO中测量了荧光量子产率和单线激发态寿命。发现在金刚烷和尿素之间具有亚甲基间隔基的分子在CH 3 CN中聚集，而在DMSO中未观察到聚集。9-氨基蒽衍生物10的聚集趋势最高在两种溶剂中聚集的pyr衍生物13。由于脲之间的分子间氢键和芳族发色团的π，π堆积，可能发生聚集。芘13可能引起的准分子激光和分子间的聚集。