2-amino-5-hydroxy-6-methyl-3H-quinazolin-4-one | 502607-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-amino-5-hydroxy-6-methyl-3H-quinazolin-4-one
• 英文别名: 2-amino-5-hydroxy-6-methylquinazolin-4(3H)-one；2-Amino-5-hydroxy-6-methylquinazolin-4(1H)-one
• CAS: 502607-49-0
• 化学式: C₉H₉N₃O₂
• 分子量: 191.189
• InChiKey: BDEFOPNHFOPDCY-UHFFFAOYSA-N

物化性质

• 沸点：
  443.1±55.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴-5-甲基靛红 在 过氧乙酸 、 硫酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 2-amino-5-hydroxy-6-methyl-3H-quinazolin-4-one
  参考文献：
  名称：

  New Straightforward Synthesis of2‐Amino‐6‐methyl‐5‐(pyridin‐4‐ylsulfanyl)‐3H‐quinazolin‐4‐one

  摘要：

  The synthesis of 2-amino-6-methyl-5-(pyridin-4-ylsulfanyl)-3H-quinazolin-4-one (1) was studied via three different synthetic routes starting from 4-bromo-5-methylisatin. The best route was established, which is a straightforward route via 2-guanidino-5-bromo-6-methyl-quinazolin-4-one (6) as the key intermediate and a one-pot synthesis by treatment of compound 6 with 4-mercaptopyridine and KOH via the Ullmann reaction. When removing the amidino group from 2-guanyl of compound 6 under strong alkaline conditions, surprisingly we found that 4-mercaptopyridine could prevent the bromo group on a quinazoline ring from substitution by a hydroxyl group. Furthermore we found that 4-mercaptopyridine analogues such as hydroxypyridinones also play a role of protecting agent in such a reaction system.

  DOI：

  10.1080/00397910600978085

文献信息

• Pyridine-4-thiol and Amphoteric Analogs: Novel Protection of Aryl Bromides in Strong Alkali
  作者：Wei-Min Chen、Chao Cheng、Bing-Zhou Li、Tse-Lok Ho、Zhao-Shuo Cai、Yuqiang Wang、Ping-Hua Sun

  DOI：10.1002/hlca.200890219

  日期：2008.11

  The use of pyridine-4-thiol (PT) to preserve certain aryl bromides in strong alkali is reported (Scheme 1). The presence of this additive or of some of its amphoteric analogs such as 3-hydroxypyridin-4(1H)-ones suppresses the replacement of the Br-substituent by hydroxide and alkoxide ions. A mechanistic interpretation of the effect is proposed.

  据报道使用吡啶-4-硫醇（PT）在强碱中保存某些芳基溴化物（方案1）。该添加剂或其某些两性类似物（例如3-羟基吡啶-4（1 H）-ones）的存在抑制了氢氧根和烷氧基离子对Br取代基的取代。提出了对该效应的机械解释。