5,5-dibromo-1-o-tolylbarbituric acid | 929032-02-0

• 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: 5,5-dibromo-1-o-tolylbarbituric acid
• 英文别名: 5,5-dibromo-1-(2-methylphenyl)-1,3-diazinane-2,4,6-trione
• CAS: 929032-02-0
• 化学式: C₁₁H₈Br₂N₂O₃
• 分子量: 376.004
• InChiKey: VPNPFQXTWLGRBA-UHFFFAOYSA-N

物化性质

• 熔点：
  174 °C(Solv: acetic acid (64-19-7))
• 密度：
  1.972±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5,5-dibromo-1-o-tolylbarbituric acid 、 alpha-D-半乳糖 在 吡啶 作用下， 以 乙醇 为溶剂， 以82%的产率得到(3'aR,5'R,6'R,7'S,7'aR)-6',7'-dihydroxy-5'-(hydroxymethyl)-1-(2-methylphenyl)spiro[1,3-diazinane-5,2'-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran]-2,4,6-trione
  参考文献：
  名称：

  Synthesis of Novel Galactopyranosyl‐Derived Spiro Barbiturates

  摘要：

  Malonic acid undergoes condensation readily with ureas to yield barbituric acids 2, which on bromination give 5,5-dibromobarbituric acids 3. Reaction of alpha-D-galactose with these 5,5-dibromo barbituric acids afforded 2,3-alpha-D-galactopyrano-1,4-dioxo-7,9-diaza-spiro[4,5]deca-6,8,10-triones 4. The structures of the products have been assigned on the basis of H-1 NMR, C-13 NMR, FAB-MS, optical activity, and elemental analysis. The title compounds are found to have antibacterial and antifungal activities.

  DOI：

  10.1080/07328300601039328
• 作为产物：
  描述：

  1-(o-tolyl)barbituric acid 在 溴 作用下， 以69%的产率得到5,5-dibromo-1-o-tolylbarbituric acid
  参考文献：
  名称：

  Synthesis of Novel Galactopyranosyl‐Derived Spiro Barbiturates

  摘要：

  Malonic acid undergoes condensation readily with ureas to yield barbituric acids 2, which on bromination give 5,5-dibromobarbituric acids 3. Reaction of alpha-D-galactose with these 5,5-dibromo barbituric acids afforded 2,3-alpha-D-galactopyrano-1,4-dioxo-7,9-diaza-spiro[4,5]deca-6,8,10-triones 4. The structures of the products have been assigned on the basis of H-1 NMR, C-13 NMR, FAB-MS, optical activity, and elemental analysis. The title compounds are found to have antibacterial and antifungal activities.

  DOI：

  10.1080/07328300601039328