5,5-diallyl-2-amino-1H-pyrimidine-4,6-dione | 862999-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: 5,5-diallyl-2-amino-1H-pyrimidine-4,6-dione
• 英文别名: 2-amino-5,5-bis(prop-2-enyl)-1H-pyrimidine-4,6-dione
• CAS: 862999-46-0
• 化学式: C₁₀H₁₃N₃O₂
• 分子量: 207.232
• InChiKey: VNEKWJAKTOUEGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5-diallyl-2-amino-1H-pyrimidine-4,6-dione 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.17h， 生成 1-(4,6-dioxo-5,5-di-n-propyl-1,4,5,6-tetrahydro-pyrimidin-2-yl)-3-isobutyl-urea
  参考文献：
  名称：

  Self-Assembly with Degenerate Prototropy

  摘要：

  This work describes a rational approach for addressing the prototropy-related problems in heterocycle-based self-assembling systems by the use of degenerate prototropy. As a proof of principle, the utility of degenerate prototropy is demonstrated herein by developing heterocycle-based AADD-type self-assembling modules that exist as "single set of protameric pair (duplex)" in both solution and solid states. These self-assembling modules are quickly accessible in good yield by reacting 2-amino-5,5-disubstituted-1H-pyrimidine-4,6-diones, available in one step by the condensation of (x,a-dialkyl malonates and free guanidine, with isocyanates. Evidence from NMR spectroscopy, ESI mass spectrometry, and single-crystal X-ray diffraction studies confirmed the formation of molecular duplexes. The effect of electronic repulsion in duplex formation is also investigated. Their ready synthetic accessibility, remarkably high propensity to crystal formation, and the novel property of degenerate prototropy would make these novel self-assembling molecules promising candidates for many proposed applications.

  DOI：

  10.1021/jo0508705
• 作为产物：
  描述：

  盐酸胍 、 二烯丙基丙二酸二乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 5,5-diallyl-2-amino-1H-pyrimidine-4,6-dione
  参考文献：
  名称：

  Efficient Electronic Communication between Two Identical Ferrocene Centers in a Hydrogen-Bonded Dimer

  摘要：

  A novel ferrocene derivative that contains a donor-donor-acceptor-acceptor (DDAA) hydrogen bonding motif forms highly stable, noncovalent dimers in chloroform and dichloromethane solutions. Its voltammetric behavior and the observation of an intervalence charge-transfer band reveal that the two equivalent ferrocene centers in the hydrogen-bonded dimer exhibit a surprisingly efficient level of electronic communication.

  DOI：

  10.1021/ja060386z

文献信息

• Dimerization of aromatic ureido pyrimidinedione derivatives: observation of an unexpected tautomer in the solid state
  作者：Lu Cui、Suresh Gadde、Atindra D. Shukla、Hao Sun、Joel T. Mague、Angel E. Kaifer

  DOI：10.1039/b717285k

  日期：——

  Ureido pyrimidinedione derivatives with phenyl, 1-naphthyl and 2-naphthyl substituents form stable dimers via quadruple hydrogen bonding, but the 1-naphthyl derivative presents an unexpected tautomer in the solid state.

  带有苯基、1-萘基和 2-萘基取代基的脲基嘧啶二酮衍生物通过四重氢键形成稳定的二聚体，但 1-萘基衍生物在固态下呈现出一种意想不到的同分异构体。
• Johnson; Hill, American Chemical Journal, 1911, vol. 46, p. 540
  作者：Johnson、Hill

  DOI：——

  日期：——
• Pichlmaier, Markus; Winter, Rainer F.; Zabel, Manfred, Journal of the American Chemical Society, 2009, vol. 131, p. 4892 - 4903
  作者：Pichlmaier, Markus、Winter, Rainer F.、Zabel, Manfred、Zalis, Stanislav

  DOI：——

  日期：——
• Carbamate-Protected (BOC and <i>O</i>-NB) 2-Aminopyrimidinedione-Based Janus G-C Nucleobase Motifs as Building Blocks for Supramolecular Assembly and Smart Polymers
  作者：Dharmendra Singh、Durga Lakshmi、Chhuttan L. Meena、Gamidi Rama Krishna、Gangadhar J. Sanjayan

  DOI：10.1021/acs.joc.3c01318

  日期：2023.11.3