6-hydroxy-7-methoxyquinazoline | 884344-38-1

• 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: 6-hydroxy-7-methoxyquinazoline
• 英文别名: 7-Methoxyquinazolin-6-ol
• CAS: 884344-38-1
• 化学式: C₉H₈N₂O₂
• 分子量: 176.175
• InChiKey: CLKLTFDXEGVZGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-hydroxy-7-methoxyquinazoline 在 过氧乙酸 、 硫酸 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 6-(3-chloropropoxy)-7-methoxyquinazolin-4-ol
  参考文献：
  名称：

  Facile and Efficient Oxidation of Quinazolines into Quinazolin-4(3H)-ones by Peracetic Acid

  摘要：

  A new approach to synthesize quinazoline-4(3H)-ones was achieved by oxidation of quinazolines using peracetic acid, which possesses some advantages of economic reagents, simplified operation, high efficiency, and environmental friendliness. Application of this method allowed us to synthesize a series of quinazolin-4(3H)-ones with different substituents at 6 and 7 positions in good to excellent yields, including the key intermediates of tyrosine kinase inhibitors such as PD153035, Erlotinib, and Gefitinib. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.805230
• 作为产物：
  描述：

  5-苄氧基-4-甲氧基-2-硝基苯甲醛 在 盐酸 、 palladium on activated charcoal 、 氢气 、 铁粉 作用下， 以 乙醇 为溶剂， 生成 6-hydroxy-7-methoxyquinazoline
  参考文献：
  名称：

  Facile and Efficient Oxidation of Quinazolines into Quinazolin-4(3H)-ones by Peracetic Acid

  摘要：

  A new approach to synthesize quinazoline-4(3H)-ones was achieved by oxidation of quinazolines using peracetic acid, which possesses some advantages of economic reagents, simplified operation, high efficiency, and environmental friendliness. Application of this method allowed us to synthesize a series of quinazolin-4(3H)-ones with different substituents at 6 and 7 positions in good to excellent yields, including the key intermediates of tyrosine kinase inhibitors such as PD153035, Erlotinib, and Gefitinib. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.805230

文献信息

• VERFAHREN ZUR HERSTELLUNG VON CHINAZOLINONDERIVATEN
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP1904458A1

  公开（公告）日：2008-04-02
• [DE] VERFAHREN ZUR HERSTELLUNG VON CHINAZOLINONDERIVATEN<br/>[EN] METHOD FOR THE PRODUCTION OF QUINAZOLINONE DERIVATIVES<br/>[FR] PROCEDE POUR PRODUIRE DES DERIVES DE QUINAZOLINONE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2007003486A1

  公开（公告）日：2007-01-11

  [EN] The invention relates to a method for producing quinazolinone derivatives of general formula (I), wherein the radicals R¹ to R³ have the meanings indicated in the claims and the description.
  [FR] L'invention concerne un procédé servant à produire des dérivés de quinazolinone de formule générale (I), dans laquelle les restes R¹ à R³ ont les significations données dans les revendications et la description.
  [DE] Die Erfindung betrifft ein Verfahren zur Herstellung von Chinazolinonderivaten der allgemeinen Formel (I) wobei die Reste R¹ bis R³ die in den Ansprüchen und der Beschreibung genannten Bedeutungen haben.
• Facile and Efficient Oxidation of Quinazolines into Quinazolin-4(3<i>H</i>)-ones by Peracetic Acid
  作者：Jian-Wen Jin、Lin Zhang、Guang-Rong Meng、Jian-Hua Zhu、Qian Zhang

  DOI：10.1080/00397911.2013.805230

  日期：2014.2

  A new approach to synthesize quinazoline-4(3H)-ones was achieved by oxidation of quinazolines using peracetic acid, which possesses some advantages of economic reagents, simplified operation, high efficiency, and environmental friendliness. Application of this method allowed us to synthesize a series of quinazolin-4(3H)-ones with different substituents at 6 and 7 positions in good to excellent yields, including the key intermediates of tyrosine kinase inhibitors such as PD153035, Erlotinib, and Gefitinib. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]