N-(6-tridecyl-4-[1H]-pyrimidinon-2-yl)-1H-imidazole-1-carboxamide | 608137-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-(6-tridecyl-4-[1H]-pyrimidinon-2-yl)-1H-imidazole-1-carboxamide
• 英文别名: 2-(1-imidazolylcarbonylamino)-6-tridecyl-4[1H]-pyrimidinone；N-(6-oxo-4-tridecyl-1H-pyrimidin-2-yl)imidazole-1-carboxamide
• CAS: 608137-36-6
• 化学式: C₂₁H₃₃N₅O₂
• 分子量: 387.525
• InChiKey: FLPYAYIAHALSPU-UHFFFAOYSA-N

物化性质

• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  88.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,7-diamino-9,9-dihexylfluorene 、 N-(6-tridecyl-4-[1H]-pyrimidinon-2-yl)-1H-imidazole-1-carboxamide 以 氯仿 为溶剂， 以72%的产率得到2,7-bis(2-ureido-6-tridecyl-4[1H]-pyrimidinonyl)-9,9-dihexylfluorene
  参考文献：
  名称：

  氢键低聚芴的合成及能量传递特性

  摘要：

  已经通过芴单体的逐步钯催化（铃木）偶联合成了一组芴低聚物。脲基嘧啶酮 (UPy) 是可通过四重氢键二聚化的官能团，连接到低聚芴的两端。所得双 UPy 封端的低聚物自组装成超分子链聚合物。为了比较，合成了具有相同低聚物长度但没有末端氢键基团的低聚芴。氢键芴链可以简单地被各种链终止剂封端，分子具有一个 UPy 基团。以这种方式，我们用低聚（对亚苯基亚乙烯基）或苝双酰亚胺封端了氢键连接的芴链。

  DOI：

  10.1021/ja052054k
• 作为产物：
  描述：

  ethyl 3-oxohexadecanoate 以 乙醇 、 氯仿 为溶剂， 反应 3.0h， 生成 N-(6-tridecyl-4-[1H]-pyrimidinon-2-yl)-1H-imidazole-1-carboxamide
  参考文献：
  名称：

  氢键合脲基嘧啶酮的简便合成

  摘要：

  封闭的异胞嘧啶异氰酸酯可通过 1,1'-羰基二咪唑 (CDI) 与异胞嘧啶反应方便地获得。产生的四重氢键结构的前体可以被分离和储存以供进一步使用。与脂肪族或芳香族胺反应得到相应的单-、双-或三官能脲基嘧啶酮衍生物，分离产率良好至极好。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200300752

文献信息

• Competitive Intramolecular Hydrogen Bonding in Oligo(ethylene oxide) Substituted Quadruple Hydrogen Bonded Systems
  作者：Tom F. A. de Greef、Marko M. L. Nieuwenhuizen、Rint P. Sijbesma、E. W. Meijer

  DOI：10.1021/jo902053t

  日期：2010.2.5

  A series of oligo(ethylene oxide) (oligoEO) substituted 2-ureido-pyrimidinones (UPy), differing in the number of ethylene oxide units and the length of the aliphatic spacer connecting the oligoEO side chain with the UPy group, have been prepared. It was found that variation in these structural parameters strongly influences the dimerization constant (Kdim) of the UPy dimer and the association constant

  已经制备了一系列的低聚（环氧乙烷）（oligoEO）取代的2-脲基-嘧啶酮（UPy），其环氧乙烷单元的数目和连接低聚EO侧链与UPy基团的脂族间隔基的长度不同。发现这些结构参数的变化强烈影响UPy二聚体的二聚化常数（K dim）和缔合常数（K a）。）UPy与2,7-diamido-1,8-naphthyridine（NaPy）在氯仿中的溶液。通过分析二聚化强度，脂族间隔基的长度和oligoEO链中EO单元数之间的关系，我们提供了强有力的证据表明氢键强度的降低是由于oligoEO链的醚原子之间竞争性的分子内氢键引起的。 UPy单元的氢键供体。
• The influence of ethylene glycol chains on the thermodynamics of hydrogen-bonded supramolecular assemblies in apolar solvents
  作者：Tom F. A. de Greef、Marko M. L. Nieuwenhuizen、Patrick J. M. Stals、Carel F. C. Fitié、Anja R. A. Palmans、Rint P. Sijbesma、E. W. Meijer

  DOI：10.1039/b806506c

  日期：——

  Substitution of hydrogen bond directed supramolecular assemblies with ethylene glycol chains leads to a reduction in the association constant in apolar solvents, where the reduction of the association constant is dependent on the length of the aliphatic spacer connecting the hydrogen bonds and the ethylene glycol chain.

  用乙二醇链替代氢键导向的超分子组装会导致在非极性溶剂中结合常数的降低，而结合常数的降低则依赖于连接氢键和乙二醇链的脂肪族连接体的长度。
• Enantioselective Cyclization of Racemic Supramolecular Polymers
  作者：A. Tessa ten Cate、Patricia Y. W. Dankers、Huub Kooijman、Anthony L. Spek、Rint P. Sijbesma、E. W. Meijer

  DOI：10.1021/ja034273g

  日期：2003.6.1

  Homochiral hydrogen-bonded cyclic assemblies are formed in dilute solutions of racemic supramolecular polymers based on the quadruple hydrogen bonding 2-ureido-4[1H]-pyrimidinone unit, as observed by 1H NMR and SEC experiments. Preorganization of the monomers and the combined binding strength of the eight hydrogen bonds result in a very high stability of the cyclic aggregates with pronounced selectivity between homochiral and heterochiral cyclic species, usually only observed in crystalline or liquid crystalline phases.
• White-Light Emitting Hydrogen-Bonded Supramolecular Copolymers Based on π-Conjugated Oligomers
  作者：Robert Abbel、Christophe Grenier、Maarten J. Pouderoijen、Jan W. Stouwdam、Philippe E. L. G. Leclère、Rint P. Sijbesma、E. W. Meijer、Albertus P. H. J. Schenning

  DOI：10.1021/ja807996y

  日期：2009.1.21

  Three different pi-conjugated oligomers (a blue-emitting oligofluorene, a green-emitting oligo(phenylene vinylene), and a red-emitting perylene bisimide) have been functionalized with self-complementary quadruple hydrogen bonding ureidopyrimidinone (UPy) units at both ends. The molecules self-assemble in solution and in the bulk, forming supramolecular polymers. When mixed together in solution, random noncovalent copolymers are formed that contain all three types of chromophores, resulting in energy transfer upon excitation of the oligofluorene energy donor. At a certain mixing ratio, a white emissive supramolecular polymer can be created in solution. In contrast to their unfunctionalized counterparts, bis-UPy-chromophores can easily be deposited as smooth thin films on surfaces by spin coating. No phase separation is observed in these films, and energy transfer is much more efficient than in solution, giving rise to white fluorescence at much lower ratios of energy acceptor to donor. Light emitting diodes based on these supramolecular polymers have been prepared from all three types of pure materials, yielding blue, green, and red devices, respectively. At appropriate mixing ratios of these three compounds, white electroluminescence is observed. This approach yields a toolbox of molecules that can be easily used to construct pi-conjugated supramolecular polymers with a variety of compositions, high solution viscosities, and tuneable emission colors.
• Conformational Control in the Cyclization of Hydrogen-Bonded Supramolecular Polymers
  作者：A. Tessa ten Cate、Huub Kooijman、Anthony L. Spek、Rint P. Sijbesma、E. W. Meijer

  DOI：10.1021/ja039408x

  日期：2004.3.1

  Bifunctional 2-ureido-4[1H]-pyrimidinone (UPy) derivatives can form small cyclic oligomers as well as long supramolecular polymers in chloroform solutions using the quadruple hydrogen-bonding motif. Ring-chain equilibria of a set of supramolecular monomers containing methyl-substituted alkyl linkers between the hydrogen-bonding UPy moieties were investigated by H-1 NMR spectroscopy and viscometry. The data were characterized in terms of critical concentration (CC, denoting the onset of polymerization) and equilibrium cyclic dimer concentration (EDC, representing preorganization of the monomer toward selective formation of cyclic dimer), Methyl substituents in the monomer were found to promote conformations favorable for cyclic dimerization, leading to an increase in both the EDC and the CC with respect to unsubstituted monomer. Furthermore, we observed an odd-even effect in the CC and EDC with increasing length of the linker between the hydrogen-bonding units. The combined results allow tuning of the critical concentration over a broad range and offer detailed information on the correlation between monomer structure, conformation, and polymerizability which may provide new insights for the study and design of other ring-chain equilibria or helix-random coil transitions.