(Z)-6-amino-2-(3,5-dibromo-4-hydroxybenzylidene)-2H-benzo[b][1,4]-oxazin-3-(4H)-one | 1245277-01-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: (Z)-6-amino-2-(3,5-dibromo-4-hydroxybenzylidene)-2H-benzo[b][1,4]-oxazin-3-(4H)-one
• 英文别名: (2Z)-6-amino-2-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-4H-1,4-benzoxazin-3-one
• CAS: 1245277-01-3
• 化学式: C₁₅H₁₀Br₂N₂O₃
• 分子量: 426.064
• InChiKey: JIUSSIJNYRNALI-ACAGNQJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-2,6-dibromo-4-{(6-nitro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-ylidene)methyl}phenyl acetate 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以70%的产率得到(Z)-6-amino-2-(3,5-dibromo-4-hydroxybenzylidene)-2H-benzo[b][1,4]-oxazin-3-(4H)-one
  参考文献：
  名称：

  Synthesis of 2-Benzylidene and 2-Hetarylmethyl Derivatives of 2H-1,4-Benzoxazin-3-(4H)-ones as Neuroprotecting Agents

  摘要：

  A wide variety of the title compounds were synthesized by conventional and microwave methods in which the main step is a condensation of an aldehyde with a 1,4-benzoxazin-3-(4H)-one. In all cases, the Z diasteromers were the major products. Of particular importance is the synthesis of novel 2-(3,5-dibromo-4-hydroxy) and 2-(4-acetoxy-3,5-dibromobenzylidene derivatives of 2H-1,4-benzoxazin-3-(4H)-ones, four of which were shown in a previous publication to exhibit potent neuroprotecting properties. The yields of titled compounds ranged from 25 to 83%.

  DOI：

  10.1080/00397910903243823

文献信息

• [EN] 1,4-BENZOXAZINE COMPOUNDS AND DERIVATIVES THEREOF AS THERAPEUTIC DRUGS FOR THE TREATMENT OF NEURODEGENERATIVE CONDITIONS<br/>[FR] COMPOSÉS DE 1,4-BENZOXAZINE, ET DÉRIVÉS DE CEUX-CI EN TANT QUE MÉDICAMENTS THÉRAPEUTIQUES POUR LE TRAITEMENT DE TROUBLES NEURODÉGÉNÉRATIFS
  申请人：UNIV TEXAS

  公开号：WO2010019911A3

  公开（公告）日：2010-05-27
• US8680094B2
  申请人：——

  公开号：US8680094B2

  公开（公告）日：2014-03-25
• Synthesis of 2-Benzylidene and 2-Hetarylmethyl Derivatives of 2<i>H</i>-1,4-Benzoxazin-3-(4<i>H</i>)-ones as Neuroprotecting Agents
  作者：Haribabu Ankati、Shashidhar Kumar Akubathini、Santosh R. D'Mello、Edward R. Biehl

  DOI：10.1080/00397910903243823

  日期：2010.7.27

  A wide variety of the title compounds were synthesized by conventional and microwave methods in which the main step is a condensation of an aldehyde with a 1,4-benzoxazin-3-(4H)-one. In all cases, the Z diasteromers were the major products. Of particular importance is the synthesis of novel 2-(3,5-dibromo-4-hydroxy) and 2-(4-acetoxy-3,5-dibromobenzylidene derivatives of 2H-1,4-benzoxazin-3-(4H)-ones, four of which were shown in a previous publication to exhibit potent neuroprotecting properties. The yields of titled compounds ranged from 25 to 83%.