5-<5-bromo-1,3-benzodioxol-6-yl>methylenepyrimidin-2,4,6(1H,3H)-trione | 141266-46-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-<5-bromo-1,3-benzodioxol-6-yl>methylenepyrimidin-2,4,6(1H,3H)-trione
• 英文别名: o-bromopiperonylidene barbiturate；5-[(6-bromo-1,3-benzodioxol-5-yl)methylene]-2,4,6(1H,3H,5H)-pyrimidinetrione；5-[(6-bromo-1,3-benzodioxol-5-yl)methylidene]-1,3-diazinane-2,4,6-trione
• CAS: 141266-46-8
• 化学式: C₁₂H₇BrN₂O₅
• 分子量: 339.102
• InChiKey: GROSIPKLEJHTBE-UHFFFAOYSA-N

物化性质

• 密度：
  1.851±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-<5-bromo-1,3-benzodioxol-6-yl>methylenepyrimidin-2,4,6(1H,3H)-trione 在 sodium chloride 作用下， 反应 0.08h， 以98%的产率得到2H-[1,3]dioxolo[4',5':6,7]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 、 6-溴-3,4-亚甲基二氧苯甲醛 以 乙醇 为溶剂， 反应 1.0h， 以96%的产率得到5-<5-bromo-1,3-benzodioxol-6-yl>methylenepyrimidin-2,4,6(1H,3H)-trione
  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

文献信息

• Nuclear magnetic resonance and molecular modeling study of exocyclic carbon–carbon double bond polarization in benzylidene barbiturates
  作者：J. Daniel Figueroa-Villar、Andreia A. Vieira

  DOI：10.1016/j.molstruc.2012.09.021

  日期：2013.2

  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.
• Synthesis of Oxadeazaflavines from Barbituric Acid and Aromatic Aldehydes
  作者：José Daniel Figueroa-Villar、Elizabete Rangel Cruz、Nedina Lucia dos Santos

  DOI：10.1080/00397919208021101

  日期：1992.4

  2H-Chromeno[2,3-d]-pyrimidine-2,4(3H)-diones were prepared directly from barbituric acid and salicylaldehydes or by thermal cyclization of the condensation product of barbituric acid and 6-bromopiperonal.
• Synthesis and mechanism of formation of oxadeazaflavines by microwave thermal cyclization of ortho-halobenzylidene barbiturates
  作者：J. Daniel Figueroa-Villar、Sandra C. G. de Oliveira

  DOI：10.1590/s0103-50532011001100012

  日期：——

  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.