4-amino-1-hexyl-1H-pyrimidin-2-one | 137732-52-6

• 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: 4-amino-1-hexyl-1H-pyrimidin-2-one
• 英文别名: N-hexylcytosine；N¹-hexylcytosine；4-amino-1-hexylpyrimidin-2-one
• CAS: 137732-52-6
• 化学式: C₁₀H₁₇N₃O
• 分子量: 195.264
• InChiKey: CLQJIQYAEDEGOV-UHFFFAOYSA-N

物化性质

• 熔点：
  216-217 °C
• 沸点：
  314.5±25.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-amino-1-hexyl-1H-pyrimidin-2-one 在 硝酸 作用下， 以 甲醇 为溶剂， 以80%的产率得到N1-hexylcytosinium nitrate
  参考文献：
  名称：

  Experimental and theoretical study of N1-hexylcytosine and N1-hexylcytosinium nitrate: the crucial role of hydrophobic and anion–π interactions

  摘要：

  We report the synthesis and X-ray characterization of N-1-hexylcytosine (1) and N-1-hexylcytosinium nitrate (2). N-1-hexylcytosine (1) does not follow the same behaviour previously described for N-1-hexylthymine and N-1-hexyluracil in the solid state. This different behavior has been analyzed by means of density functional theory (DFT) calculations including the latest available correction for dispersion (D3). In addition hydrophobic and anion-pi noncovalent interactions play a key role in stabilizing the 3D architectures of the compounds, which have been energetically studied using theoretical calculations and compared with similar structures retrieved from the Cambridge Structural Database (CSD). The anion-pi-anion binding mode observed for nitrate in compound 2 is also observed in several crystal structures involving cytosine ring coordinated to transition metals. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.099
• 作为产物：
  描述：

  N-(1-hexyl-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide 以 solution 、 氨 、 甲醇 为溶剂， 反应 48.0h， 以afforded 4-Amino-1-hexyl-1H-pyrimidin-2-one (C) as a colourless solid (0.052 g, 63%)的产率得到4-amino-1-hexyl-1H-pyrimidin-2-one
  参考文献：
  名称：

  Supramolecular Polymers

  摘要：

  该发明涉及新型以胞嘧啶为基础的模块，特别是它们在线性多氢键阵列中的应用，以形成公式（II）的超分子聚合物，并将其用于超分子材料中。

  公开号：

  US20090005519A1

文献信息

• Experimental and theoretical study of thymine and cytosine derivatives: the crucial role of weak noncovalent interactions
  作者：Miquel Barceló-Oliver、Beatriz A. Baquero、Antonio Bauzá、Angel García-Raso、Angel Terrón、Ignasi Mata、Elies Molins、Antonio Frontera

  DOI：10.1039/c2ce25580d

  日期：——

  In this paper we report the synthesis of N1-hexylthymine (1), N1-hexylcytosine (2), N1-hexylcytosine hydrobromide (3) and [(N1-hexylcytosinium)·(N1-hexylcytosine)]2·[Cl2Hg(μ-Cl)2HgCl2] (4) (the hemiprotonated form of the N1-hexylcytosine forming a CHC+ pair with carbonyl-amino symmetric and N3–N3 recognitions) and X-ray characterization of compounds 1, 3 and 4. In the solid state, N1-hexylthymine 1 follows exactly the same behaviour as N1-hexyluracil. In addition to strong hydrogen bonding interactions, various weak forces, i.e. C–H/π, carbonyl–carbonyl (CO⋯CO) and anion–π interactions (between the bromide and N1 of cytosine in 3), play a key role in stabilizing the 3D architectures of the compounds. The theoretical calculations allow estimation of the strength of these contacts and how they influence each other.

  在本文中，我们报告了N1-己基胸腺嘧啶（1），N1-己基胞嘧啶（2），N1-己基胞嘧啶溴化氢盐（3）以及[(N1-己基胞嘧啶阳离子)·(N1-己基胞嘧啶)]2·[Cl2Hg(μ-Cl)2HgCl2]（4）（N1-己基胞嘧啶的半质子化形式，与羰基-氨基对称及N3–N3识别形成CHC+对）和化合物1、3与4的X射线表征。在固态中，N1-己基胸腺嘧啶1的行为与N1-己基尿嘧啶完全相同。除了强氢键相互作用外，各种弱作用力，即C–H/π相互作用、羰基-羰基（CO⋯CO）和阴离子-π相互作用（在3中溴化物与胞嘧啶的N1之间），在稳定化合物的三维结构中起着关键作用。理论计算使我们能够估计这些相互接触的强度及其相互影响。
• Cytosine modules in quadruple hydrogen bonded arrays
  作者：Elisabetta Greco、Abil E. Aliev、Valerie G. H. Lafitte、Kason Bala、David Duncan、Laura Pilon、Peter Golding、Helen C. Hailes

  DOI：10.1039/c0nj00197j

  日期：——

  Cytosine modules have been investigated for applications in supramolecular quadruple hydrogen bonded arrays. Notably, the importance of the C-5–H in the formation of unfolded and folded arrays by substitution to C-5–F was established. In addition, the incorporation of different alkyl chain lengths at N-1 and N-9 indicated that longer alkyl chains give rise to more of the unfolded rotamer, with the chain length and degree of unsaturation at N-1 having the major effect. Methyl cytosine modules were also able to readily form hetero-associated Upy–UCyt dimers as efficiently as the hexyl cytosine modules and a polyadipate telechelic polymer was used to prepare cytosine polymers.

  胞嘧啶模块已被研究用于超分子四重氢键阵列的应用。值得注意的是，C-5–H在通过替换为C-5–F形成未折叠和折叠阵列中的重要性得到了确立。此外，在N-1和N-9处引入不同的烷基链长度表明，较长的烷基链会产生更多的未折叠转态，而链长和N-1处的不饱和度对这一效果有主要影响。甲基胞嘧啶模块也能够像己基胞嘧啶模块一样高效地形成异构关联的Upy–UCyt二聚体，同时使用聚己二酸酯的末端接枝聚合物来制备胞嘧啶聚合物。
• Synthesis, X-ray characterization and regium bonding interactions of a trichlorido(1-hexylcytosine)gold(<scp>iii</scp>) complex
  作者：Angel Terrón、Jordi Buils、Tiddo J. Mooibroek、Miquel Barceló-Oliver、Angel García-Raso、Juan J. Fiol、Antonio Frontera

  DOI：10.1039/d0cc00505c

  日期：——

  Herein we report the synthesis and X-ray characterization of a gold(iii) complex of 1-hexylcytosine via N(3). The AuCl3N complexes stack on top of each other by reciprocal [AuCl] regium bonding interactions. After the first example 35 years ago, this is the second available structure of a cytosine nucleobase model complexed to gold(iii).

  本文中，我们通过N（3）报告了1-己基胞嘧啶的金（iii）配合物的合成和X射线表征。AuCl3N络合物通过相互的[AuCl] reg键相互作用相互堆叠。在35年前的第一个例子之后，这是与金（iii）络合的胞嘧啶核碱基模型的第二个可用结构。
• Supramolecular polymers
  申请人：The Secretary of State for Defence

  公开号：US08076426B2

  公开（公告）日：2011-12-13

  The invention concerns novel cytosine based modules and in particular their application in linear multiple hydrogen bonded arrays to form supramolecular polymers of the formula (II): and the use of these in supramolecular materials.

  本发明涉及一种新型的以胞嘧啶为基础的模块，特别是它们在线性多氢键阵列中的应用，以形成公式（II）的超分子聚合物，并将其用于超分子材料中。
• Construction of photoswitchable urea-based multiple H-bonding motifs
  作者：Lan-Yun Chen、Lu Wei、Yu Hai、Li-Juan Liu、Kang-Da Zhang、Tian-Guang Zhan

  DOI：10.1016/j.tet.2023.133343

  日期：2023.2

  photoactive urea-based multiple H-bonding motifs were rationally constructed by tethering the photoisomerizable azobenzene units aside to the urea groups of several typical urea-constituted H-bonding arrays. Taking the integrated azo units as photoswitches, their phototriggered E/Z isomerization can be used to reversibly manipulate the locking (with intramolecular H-bonds) and unlocking (without intramolecular

  在本文中，通过将可光致异构化的偶氮苯单元束缚在几个典型的尿素构成的氢键阵列的尿素基团旁边，合理地构建了一系列基于光活性尿素的多重氢键基序。将集成的偶氮单元作为光开关，它们的光触发E / Z 异构化可用于分别可逆地操纵这些基序的尿素氢键位点的锁定（具有分子内氢键）和解锁（无分子内氢键） . 此功能使E / Z光异构尿素衍生物表现出可切换的分子间氢键亲和力，从而在不同光源照射下实现独特的光控自/异互补多氢键二聚化。受益于尿素基团的广泛应用，开发这种具有光开关二聚亲和力的尿素基多氢键系统有望为构建丰富的尿素基氢键超分子组装系统和材料提供一种普遍适用的方法。光调节特性和功能。