2-amino-5,5-dibenzyl-1H-pyrimidine-4,6-dione | 862999-47-1

• 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: 2-amino-5,5-dibenzyl-1H-pyrimidine-4,6-dione
• CAS: 862999-47-1
• 化学式: C₁₈H₁₇N₃O₂
• 分子量: 307.352
• InChiKey: QGWCUIUHNYXTRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  2-amino-5,5-dibenzyl-1H-pyrimidine-4,6-dione 、 十二烷基伯胺 、 三光气 在 N,N-二异丙基乙胺 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到1-(5,5-dibenzyl-4,6-dioxo-1,4,5,6-tetrahydro-pyrimidin-2-yl)-3-dodecyl-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 、 二苄基丙二酸二乙酯 在 sodium 作用下， 以 乙醇 为溶剂， 以64%的产率得到2-amino-5,5-dibenzyl-1H-pyrimidine-4,6-dione
  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

文献信息

• Self-Assembly with Degenerate Prototropy
  作者：Pranjal K. Baruah、Rajesh Gonnade、Usha D. Phalgune、Gangadhar J. Sanjayan

  DOI：10.1021/jo0508705

  日期：2005.8.1

  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.