6-[3,4,5-tris(dodecyloxy)phenyl]isocytosine | 210709-58-3

• 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: 6-[3,4,5-tris(dodecyloxy)phenyl]isocytosine
• 英文别名: 6-[3,4,5-tri(dodecyloxy)phenyl]isocytosine；2-amino-4-(3,4,5-tridodecoxyphenyl)-1H-pyrimidin-6-one
• CAS: 210709-58-3
• 化学式: C₄₆H₈₁N₃O₄
• 分子量: 740.167
• InChiKey: CVWYVRRAYMHPIX-UHFFFAOYSA-N

物化性质

• 沸点：
  781.9±70.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  17
• 重原子数：
  53
• 可旋转键数：
  37
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-[3,4,5-tris(dodecyloxy)phenyl]isocytosine 以 氘代氯仿 、 氯仿 为溶剂， 反应 2.5h， 生成 1-(4-Bromo-phenyl)-3-[4-oxo-6-(3,4,5-tris-dodecyloxy-phenyl)-1,4-dihydro-pyrimidin-2-yl]-urea
  参考文献：
  名称：

  基于四氢键的金属卟啉的环状四聚体。

  摘要：

  [反应：见正文]本文描述了由具有两个自互补四氢键合单元的易于合成的金属卟啉选择性形成环状四聚体的方法。极强的四氢键合单元2-ureido-4 [1H]-嘧啶酮能够在宽浓度范围内基于四苯基卟啉衍生物形成稳定的环状四聚体。这种氢键结合的四聚体是一种新的功能单元，可用于超分子卟啉组装体的高级结构。

  DOI：

  10.1021/ol060488u
• 作为产物：
  描述：

  3-Oxo-2-(3,4,5-tris-dodecyloxy-benzoyl)-butyric acid ethyl ester 在 sodium methylate 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 6-[3,4,5-tris(dodecyloxy)phenyl]isocytosine
  参考文献：
  名称：

  Strong Dimerization of Ureidopyrimidones via Quadruple Hydrogen Bonding

  摘要：

  6-Methyl-2-butylureidopyrimidone dimerizes via four hydrogen bonds in the solid state as well as in CHCl3 solution via a donor-donor-acceptor-acceptor (DDAA) array of hydrogen bonding sites in the 4[1H]-pyrimidinone tautomer. An intramolecular hydrogen bond from the pyrimidine NH group to the urea oxygen atom preorganizes the molecules for dimerization. The dimerization constant of the dimer in CHCl3 exceeds 10(6) M-1. In CHCl3 containing DMSO, the dimer is in equilibrium with the monomeric 6[1H]-pyrimidinone tautomer. In 6-phenyl-2-butylureidopyrimidone, the 4[1H]-pyrimidinone tautomer coexists with the pyrimidin-4-ol form, which dimerizes with similar high dimerization constants via four hydrogen bonds in a DADA array. The latter tautomer predominates in derivatives with electronegative 6-substituents, like 6-nitrophenyl- and 6-trifluoromethyl-2-butylureidopyrimidone. Due to its simple preparation and high dimerization constant, the ureidopyrimidone functionality is a useful building block far supramolecular chemistry.

  DOI：

  10.1021/ja974112a

文献信息

• Controlled Sol–Gel Transitions by Actuating Molecular Machine Based Supramolecular Polymers
  作者：Antoine Goujon、Giacomo Mariani、Thomas Lang、Emilie Moulin、Michel Rawiso、Eric Buhler、Nicolas Giuseppone

  DOI：10.1021/jacs.7b00983

  日期：2017.4.5

  [c2]daisy chain rotaxanes (i.e., molecular muscles) can be linked into main-chain Upy-based supramolecular polymers. We then reveal by an in depth quantitative study that the pH actuation of the mechanically active rotaxane at the nanoscale influences the physical reticulation of the polymer chains by changing the supramolecular behavior of the Upy units. This nanoactuation within the local structure of the

  在聚合物科学中实施人工分子机器是挑战化学家和物理学家以获取全新一类智能材料的重要目标。为了设计这样的系统，将机械驱动从纳米级放大到大块材料中的宏观响应是一个核心问题。在本文中，我们展示了双稳态 [c2] 菊花链轮烷（即分子肌肉）可以连接到主链 Upy 型超分子聚合物中。然后，我们通过深入的定量研究揭示，纳米级机械活性轮烷的 pH 驱动通过改变 Upy 单元的超分子行为影响聚合物链的物理网状结构。
• 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。
• Helical Supramolecular Aggregates Based on Ureidopyrimidinone Quadruple Hydrogen Bonding
  作者：J. H. K. Ky Hirschberg、Rolf A. Koevoets、Rint P. Sijbesma、E. W. Meijer

  DOI：10.1002/chem.200204495

  日期：2003.9.5

  Dodecane solutions of compounds 3, 4 b, and 7 b display a Cotton effect at the absorption band of the phenyl-pyrimidinone unit. Amplification of chirality was observed in mixtures of 7 a and 7 b, but not in mixtures of 4 a and 4 b, indicating that 7 a and 7 b form mixed polymeric aggregates with a helical architecture in dodecane solution, whereas 4 a and 4 b do not. The Cotton effect is lost upon increasing

  制备了一系列基于脲基嘧啶酮四氢键合单元的单官能和双官能化合物2-7，以研究这些化合物在本体和溶液中的聚集方式。化合物2-7表现出热致液晶性质，如通过差示扫描量热法和光学偏振显微镜所证明的。通过在对准的样品上的X射线衍射确认2a的有序六方盘状（D（ho））相的存在。在氯仿中，双功能化合物在毫摩尔浓度下形成环状二聚体，这些二聚体与高于临界浓度的线性物质平衡存在，取决于间隔物的结构，该临界浓度可能为6 mM至大于260 mM。在氯仿中的圆二色性测量未显示出棉花效应。化合物3、4b和7b的十二烷溶液在苯基-嘧啶酮单元的吸收带上表现出棉花效应。在7a和7b的混合物中观察到手性的放大，但在4a和4b的混合物中未观察到，表明7a和7b在十二烷溶液中形成具有螺旋结构的混合聚合物聚集体，而4a和4b不要。升高温度会失去棉花效应。在25摄氏度下3失去了一半的螺旋度，在60摄氏度下4 b失去了一半的螺旋度，这表明带有较短间隔基的3形成的稳定性不如4
• Cyclic Tetramer of a Metalloporphyrin Based on a Quadruple Hydrogen Bond
  作者：Haruki Ohkawa、Akihiro Takayama、Satoshi Nakajima、Hiroyuki Nishide

  DOI：10.1021/ol060488u

  日期：2006.5.1

  formation of a cyclic tetramer from a readily synthesized metalloporphyrin with two self-complementary quadruple hydrogen-bonding units. The extremely strong quadruple hydrogen-bonding unit, 2-ureido-4[1H]-pyrimidinone, enabled the formation of a stable cyclic tetramer based on a tetraphenylporphyrin derivative over a wide concentration range. This hydrogen-bonded tetramer is a new functional unit

  [反应：见正文]本文描述了由具有两个自互补四氢键合单元的易于合成的金属卟啉选择性形成环状四聚体的方法。极强的四氢键合单元2-ureido-4 [1H]-嘧啶酮能够在宽浓度范围内基于四苯基卟啉衍生物形成稳定的环状四聚体。这种氢键结合的四聚体是一种新的功能单元，可用于超分子卟啉组装体的高级结构。
• Strong Dimerization of Ureidopyrimidones via Quadruple Hydrogen Bonding
  作者：Felix H. Beijer、Rint P. Sijbesma、Huub Kooijman、Anthony L. Spek、E. W. Meijer

  DOI：10.1021/ja974112a

  日期：1998.6.13

  6-Methyl-2-butylureidopyrimidone dimerizes via four hydrogen bonds in the solid state as well as in CHCl3 solution via a donor-donor-acceptor-acceptor (DDAA) array of hydrogen bonding sites in the 4[1H]-pyrimidinone tautomer. An intramolecular hydrogen bond from the pyrimidine NH group to the urea oxygen atom preorganizes the molecules for dimerization. The dimerization constant of the dimer in CHCl3 exceeds 10(6) M-1. In CHCl3 containing DMSO, the dimer is in equilibrium with the monomeric 6[1H]-pyrimidinone tautomer. In 6-phenyl-2-butylureidopyrimidone, the 4[1H]-pyrimidinone tautomer coexists with the pyrimidin-4-ol form, which dimerizes with similar high dimerization constants via four hydrogen bonds in a DADA array. The latter tautomer predominates in derivatives with electronegative 6-substituents, like 6-nitrophenyl- and 6-trifluoromethyl-2-butylureidopyrimidone. Due to its simple preparation and high dimerization constant, the ureidopyrimidone functionality is a useful building block far supramolecular chemistry.