1,3-bis{[3-(naphthalen-1-yl)ureido]methyl}adamantane | 1246887-93-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3-bis{[3-(naphthalen-1-yl)ureido]methyl}adamantane
• 英文别名: 1-Naphthalen-1-yl-3-[[3-[(naphthalen-1-ylcarbamoylamino)methyl]-1-adamantyl]methyl]urea
• CAS: 1246887-93-3
• 化学式: C₃₄H₃₆N₄O₂
• 分子量: 532.685
• InChiKey: MMCSPNHJWYBABB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  1,3-bis{[3-(naphthalen-1-yl)ureido]methyl}adamantane 、 四丁基醋酸铵 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Adamantane bisurea derivatives: anion binding in the solution and in the solid state

  摘要：

  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.

  DOI：

  10.1016/j.tet.2012.11.030
• 作为产物：
  描述：

  1,3-金刚烷二乙酸 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 1,3-bis{[3-(naphthalen-1-yl)ureido]methyl}adamantane
  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

• 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。
• 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.