N-(4-oxo-6-butyl-1,4-dihydropyrimidin-2-yl)-1H-imidazole-1-carboxamide

• 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-(4-oxo-6-butyl-1,4-dihydropyrimidin-2-yl)-1H-imidazole-1-carboxamide
• 英文别名: N-(4-butyl-6-oxo-1H-pyrimidin-2-yl)imidazole-1-carboxamide
• 化学式: C₁₂H₁₅N₅O₂
• 分子量: 261.283
• InChiKey: SOYUZTBWKWNCDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  3-氨甲基吡啶 、 N-(4-oxo-6-butyl-1,4-dihydropyrimidin-2-yl)-1H-imidazole-1-carboxamide 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以77%的产率得到1-(4-oxo-6-butyl-1,4-dihydropyrimidin-2-yl)-3-(pyridine-3-ylmethyl)urea
  参考文献：
  名称：

  Self-Assembled Squares and Triangles by Simultaneous Hydrogen Bonding and Metal Coordination

  摘要：

  Through the combination of hydrogen bonding and metal-templated self-assembly, molecular squares and molecular triangles are observed in chloroform solution upon the complexation of hydrogen-bonded dimers of para-pyridyl-substituted 2-ureido-4-[1H]-pyrlmidinone (UPy) and an appropriate cis-substituted palladium complex. Molecular modeling studies and NMR analysis confirmed the presence of two distinct structures In solution: the tubular structure of the molecular square and propeller-bowl structure of the molecular triangle.

  DOI：

  10.1021/ol400326r
• 作为产物：
  描述：

  2-己酮 在 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 mineral oil 为溶剂， 反应 0.5h， 生成 N-(4-oxo-6-butyl-1,4-dihydropyrimidin-2-yl)-1H-imidazole-1-carboxamide
  参考文献：
  名称：

  Self-Assembled Squares and Triangles by Simultaneous Hydrogen Bonding and Metal Coordination

  摘要：

  Through the combination of hydrogen bonding and metal-templated self-assembly, molecular squares and molecular triangles are observed in chloroform solution upon the complexation of hydrogen-bonded dimers of para-pyridyl-substituted 2-ureido-4-[1H]-pyrlmidinone (UPy) and an appropriate cis-substituted palladium complex. Molecular modeling studies and NMR analysis confirmed the presence of two distinct structures In solution: the tubular structure of the molecular square and propeller-bowl structure of the molecular triangle.

  DOI：

  10.1021/ol400326r

文献信息

• Selective Formation of <i>S</i>₄- and <i>T</i>-Symmetric Supramolecular Tetrahedral Cages and Helicates in Polar Media Assembled via Cooperative Action of Coordination and Hydrogen Bonds
  作者：Qixun Shi、Xiaohong Zhou、Wei Yuan、Xiaoshi Su、Algirdas Neniškis、Xin Wei、Lukas Taujenis、Gustautas Snarskis、Jas S. Ward、Kari Rissanen、Javier de Mendoza、Edvinas Orentas

  DOI：10.1021/jacs.0c00722

  日期：2020.2.19

  the hydrogen-bonding unit with respect to the metal coordinating site results in a T-symmetric cage, whereas by introducing flexibility either through a methylene linker or rotating benzene ring allows the formation of S4-symmetric cages with self-filled interior. In addition, the possibility to select between tetrahedral cages or helicates, and to control the dimensions of the aggregate, has been demonstrated

  我们报告了包含四重氢键基序和金属配位 2,2'-联吡啶单元的新型超分子单体的合成和自组装研究。当与 Fe2+ 或 Zn2+ 等金属离子混合时，即使在高极性乙腈或甲醇溶剂中，也会以定量产率和完全非对映选择性形成四面体笼络合物。所获得的复合物的对称性已被证明在很大程度上取决于配体的灵活性。限制氢键单元相对于金属配位点的旋转会导致 T 对称笼，而通过亚甲基连接体或旋转苯环引入灵活性，可以形成具有自填充的 S4 对称笼内部的。此外，通过使用外部氢键分子插入物或通过改变金属离子半径（Hg2+ 与 Fe2+）的三组件组装，已经证明了在四面体笼或螺旋体之间进行选择以及控制聚集体尺寸的可能性。对具有不同大小配体的单个 Fe2+ 配合物的自分类研究揭示了它们对配体扰乱的惰性。
• The Convenient Synthesis of Hydrogen-Bonded Ureidopyrimidinones
  作者：Henk M. Keizer、Rint P. Sijbesma、E. W. Meijer

  DOI：10.1002/ejoc.200300752

  日期：2004.6

  Blocked isocytosine isocyanates are conveniently obtained by the reaction of 1,1′-carbonyldiimidazole (CDI) with isocytosines. The resulting precursors for quadruple hydrogen-bonded structures can be isolated and stored for further use. Reaction with either aliphatic or aromatic amines gives the corresponding mono-, bi-, or trifunctional ureidopyrimidinone derivatives in good to excellent isolated

  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)
• Reversible hydrogen-bonded polymerization regulated by allosteric metal templation
  作者：Tangxin Xiao、Weiwei Zhong、Weiwei Yang、Lijie Qi、Yan Gao、Andrew C.-H. Sue、Zheng-Yi Li、Xiao-Qiang Sun、Chen Lin、Leyong Wang

  DOI：10.1039/d0cc06381a

  日期：——

  common in biology, but have not been fully explored in the control of supramolecular polymerization. Herein, ditopic UPy derivatives with acyclic crown ether-like spacers were designed and synthesized, which can undergo supramolecular polymerization through quadruple hydrogen bonding. Upon the addition of K+, drastic molecular conformational change to the U-shape is induced by metal-coordination, reconfiguring

  变构作用在生物学中很常见，但在控制超分子聚合方面尚未得到充分研究。本文中，设计并合成了具有无环冠状醚样间隔基的对位UPy衍生物，其可以通过四氢键键合进行超分子聚合。添加K +后，金属配位作用导致U形分子构象发生剧烈变化，从而将远端的UPy位点重新配置为形成离散的环状二聚体。有趣的是，超分子聚合可以通过用水萃取简单地除去K +来恢复。
• Supramolecular organic network assembled from quadruple hydrogen-bonding motifs
  作者：Xue Huang、Yan-Chao Zhao、Bao-Hang Han

  DOI：10.1039/c6cc02206e

  日期：——

  A rigid triptycene derivative with three 2-ureido-4[1H]-pyrimidinone (UPy) terminals was employed to construct a supramolecular hydrogen-bonded organic polymer (HOP-1).

  使用一种带有三个2-尿素基-4[1H]-嘧啶酮（UPy）末端的刚性三环衍生物构建了一种超分子氢键有机聚合物（HOP-1）。
• Self-Assembled Squares and Triangles by Simultaneous Hydrogen Bonding and Metal Coordination
  作者：Laura J. Marshall、Javier de Mendoza

  DOI：10.1021/ol400326r

  日期：2013.4.5

  Through the combination of hydrogen bonding and metal-templated self-assembly, molecular squares and molecular triangles are observed in chloroform solution upon the complexation of hydrogen-bonded dimers of para-pyridyl-substituted 2-ureido-4-[1H]-pyrlmidinone (UPy) and an appropriate cis-substituted palladium complex. Molecular modeling studies and NMR analysis confirmed the presence of two distinct structures In solution: the tubular structure of the molecular square and propeller-bowl structure of the molecular triangle.