1-(n-butyl)-5-phenylbarbituric acid | 92256-09-2

• 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: 1-(n-butyl)-5-phenylbarbituric acid
• 英文别名: 1-Butyl-5-phenyl-1,3-diazinane-2,4,6-trione
• CAS: 92256-09-2
• 化学式: C₁₄H₁₆N₂O₃
• 分子量: 260.293
• InChiKey: QRFRPXOWZLDYIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(n-butyl)-5-phenylbarbituric acid 在 硫酸 、 potassium nitrate 作用下， 以19%的产率得到1-n-butyl-5-(4-nitrophenyl)barbituric acid
  参考文献：
  名称：

  Probing Molecular Recognition in the Solid-State by Use of an Enolizable Chromophoric Barbituric Acid

  摘要：

  Complex formation of the enolizable chromophor 1-n-butyl-5-(4-nitrophenyl)barbituric acid 1 with multiple binding sites for supramolecular assemblies and its corresponding adducts produced with the Proton Sponge (1,8-bis(dimethylamino)naphthalene), PS) and the adenine-mimetic 2,6-diacetamidopyridine (DAC) have been studied by means of solid-state proton NMR spectroscopy under fast magic-angle spinning, X-ray analysis, and UV/vis spectroscopy. Both NMR data and X-ray results reveal that the enolic chromophor undergoes self-aggregation to hydrogen-bonded dimers which are involved in stacked arrangements. Depending on the nature of the added base, this dimeric assembly is preserved in the formed enolate anion but can be broken in the presence of complementary hydrogen-bonding pattern leading to supramolecular complexes. Molecular recognition of these structural different bases significantly influences the chromophoric pi-system of 1.

  DOI：

  10.1021/jo800598z
• 作为产物：
  描述：

  N-丁基脲 、 苯基丙二酸二乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以45%的产率得到1-(n-butyl)-5-phenylbarbituric acid
  参考文献：
  名称：

  Probing Molecular Recognition in the Solid-State by Use of an Enolizable Chromophoric Barbituric Acid

  摘要：

  Complex formation of the enolizable chromophor 1-n-butyl-5-(4-nitrophenyl)barbituric acid 1 with multiple binding sites for supramolecular assemblies and its corresponding adducts produced with the Proton Sponge (1,8-bis(dimethylamino)naphthalene), PS) and the adenine-mimetic 2,6-diacetamidopyridine (DAC) have been studied by means of solid-state proton NMR spectroscopy under fast magic-angle spinning, X-ray analysis, and UV/vis spectroscopy. Both NMR data and X-ray results reveal that the enolic chromophor undergoes self-aggregation to hydrogen-bonded dimers which are involved in stacked arrangements. Depending on the nature of the added base, this dimeric assembly is preserved in the formed enolate anion but can be broken in the presence of complementary hydrogen-bonding pattern leading to supramolecular complexes. Molecular recognition of these structural different bases significantly influences the chromophoric pi-system of 1.

  DOI：

  10.1021/jo800598z

文献信息

• Barbituric Acid as a Substituent at Aryl Methylium Ions
  作者：Stefan Spange、Mirko Bauer、Bernhard Walfort、Heinrich Lang

  DOI：10.1021/jo061196+

  日期：2006.9.1

  Activation of different benzophenone derivatives with triflic anhydride for electrophilic aromatic substitution of 5-phenylbarbituric acids leads to regioselective formation of the ortho-substituted product. The resulting triphenylmethylium salt can be isolated when the Michlers ketone is used. More electrophilic cations form cyclic enol ethers such as 1-n-butyl-9,9-diaryl-1,9-dihydro-10-oxa-1,3-diazaphenanthrene-2

  用三氟甲磺酸酐将不同的二苯甲酮衍生物活化以进行5-苯基巴比妥酸的亲电芳香取代反应，会导致邻位取代产物的区域选择性形成。当使用米氏酮时，可以分离得到的三苯基甲基盐。更多的亲电子阳离子形成环状烯醇醚，例如1-正丁基-9,9-二芳基-1,9-二氢-10-氧杂-1,3-二氮杂菲-2,4-二酮。或者，已经研究了与2，6-二乙酰氨基吡啶形成的超分子复合物以及碳正离子的产生。尽管在稀酸中仅发生羰基氧之一的质子化，但在96％的硫酸中观察到了环状烯醇醚向碳正离子的开环。
• Bauer, Mirko; Spange, Stefan, ARKIVOC, 2012, vol. 2012, # 3, p. 38 - 48
  作者：Bauer, Mirko、Spange, Stefan

  DOI：——

  日期：——