5-(2-bromobenzylidene)barbituric acid | 57270-77-6

• 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: 5-(2-bromobenzylidene)barbituric acid
• 英文别名: o-Brombenzyliden-barbitursaeure；o-bromobenzylidene barbiturate；5-(2-Bromobenzylidene)-2,4,6(1H,3H,5H)-pyrimidinetrione；5-[(2-bromophenyl)methylidene]-1,3-diazinane-2,4,6-trione
• CAS: 57270-77-6
• 化学式: C₁₁H₇BrN₂O₃
• 分子量: 295.092
• InChiKey: RKGKIGKAOFHESE-UHFFFAOYSA-N

物化性质

• 密度：
  1.715±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933540000

反应信息

• 作为反应物：
  描述：

  5-(2-bromobenzylidene)barbituric acid 在 碳酸氢钠 作用下， 反应 0.17h， 以47%的产率得到2H-chromeno<2,3-d>pyrimidine-2,4(3H)-dione
  参考文献：
  名称：

  Synthesis and mechanism of formation of oxadeazaflavines by microwave thermal cyclization of ortho-halobenzylidene barbiturates

  摘要：

  The thermal cyclization reaction of o-halobenzylidene barbiturates was developed as an efficient and simple method for the preparation of oxadeazaflavines. The use of solid state reaction conditions with microwave irradiation afforded the products in 5 min with 47 to 98% yield. Experimental synthetic results and thermogravimetric reaction analyses agree with the molecular modeling mechanism simulation, indicating that this reaction occurs through an intramolecular hetero-Diels-Alder cyclization followed by fast re-aromatization.

  DOI：

  10.1590/s0103-50532011001100012
• 作为产物：
  描述：

  巴比妥酸 、 邻溴苯甲醛 以 乙醇 、 水 为溶剂， 反应 0.5h， 以90%的产率得到5-(2-bromobenzylidene)barbituric acid
  参考文献：
  名称：

  Nuclear magnetic resonance and molecular modeling study of exocyclic carbon–carbon double bond polarization in benzylidene barbiturates

  摘要：

  Benzylidene barbiturates are important materials for the synthesis of heterocyclic compounds with potential for the development of new drugs. The reactivity of benzylidene barbiturates is mainly controlled by their exocyclic carbon-carbon double bond. In this work, the exocyclic double bond polarization was estimated experimentally by NMR and correlated with the Hammett sigma values of the aromatic ring substituents and the molecular modeling calculated atomic charge difference. It is demonstrated that carbon chemical shift differences and NBO charge differences can be used to predict their reactivity. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.09.021

文献信息

• Regiospecific synthesis of novel <i>spiro</i>‐pyrimidobarbiturates with promising antibacterial activities
  作者：Bahgat R. M. Hussein、Amr H. Moustafa

  DOI：10.1002/jhet.4770

  日期：2024.2

  In this work, a novel series of 9-amino-7-aryl-11-imino-2,4,8,10-tetraazaspiro[5.5]undeca-7,9-diene-1,3,5-triones 3a-l was synthesized via the treatment of cyanoguanidine 1 with respective arylidene barbituric acids 2a-l in dry pyridine. The products were evaluated for in vitro antibacterial activity against Bacillus cereus (+G), Staphylococcus aureus (+G), Pseudomonas aeruginosa (−G) and Escherichia

  在这项工作中，一系列新的 9-amino-7-aryl-11-imino-2,4,8,10-tetraazaspiro[5.5]undeca-7,9-diene-1,3,5-triones 3a-l通过在无水吡啶中用相应的亚芳基巴比妥酸2a-1处理氰基胍1来合成。评估产品对蜡样芽孢杆菌（+G）、金黄色葡萄球菌（+G）、铜绿假单胞菌（-G）和大肠杆菌（-G）的体外抗菌活性。结果表明，一些测试产品是有前途的抗菌药物。
• Barbituric acid in the synthesis of fused 1,7-phenanthroline derivatives
  作者：N. G. Kozlov、A. B. Tereshko

  DOI：10.1134/s1070428014070124

  日期：2014.7
• Synthesis and antibacterial activity of 2-substituted 5-(1,2-diarylethyl)-4,6-dichloropyrimidine derivatives
  作者：Y Fellahi、P Dubois、D Mandin、JE Ombetta-Goka、J Guenzet、JP Chaumont、Y Frangin

  DOI：10.1016/0223-5234(96)88279-1

  日期：1995.1

  A series of 5-(1,2-diarylethyl)-2,4,6-trichloropyrimidines and 2-amino- and 2-(1-piperazinyl)-5-(1,2-diarylethyl)-4,6-dichloropyrimidines were synthesized via organozinc reagents. These new pyrimidine derivatives were tested against human bacterial flora. Biological tests showed that 5-[1-(4-chlorophenyl)-2-phenylethyl]-2,4,6-trichloropyrimidine is very active against a wide range of bacterial flora of the axilla and foot, while 2-amino and 2-(1-piperazinyl)-4,6- dichloropyrimidine derivatives display a great selectivity against Corynebacterium xerosis and Arcanobacterium haemolyticum of the human axilla.