2',3',5,8-tetrahydroxythioflavone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻喃类
• 英文名称: 2',3',5,8-tetrahydroxythioflavone
• 英文别名: 2-(2,3-Dihydroxyphenyl)-5,8-dihydroxythiochromen-4-one
• 化学式: C₁₅H₁₀O₅S
• 分子量: 302.307
• InChiKey: AWHUZYBZLBEUGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 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：
  123
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3-二苄氧基苯甲醛 在 氢氧化钾 、 三氯化铝 、 四丁基氯化铵 、 十六烷基三甲基溴化铵 、 对甲苯磺酸 、 silver nitrate 、 N,N-二甲基苯胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 79.0h， 生成 2',3',5,8-tetrahydroxythioflavone
  参考文献：
  名称：

  Synthesis and Reactivity of 5,8-Dihydroxythioflavanone Derivatives

  摘要：

  The synthesis of substituted chalcones, thioflavanones, and thioflavones hydroxylated in both A and B rings is described. Acetoquinone (1) was transformed into 2,5-dihydroxy-6-(p-methoxybenzylmercapto)acetophenone (2) and subsequently into its 2,5-dimethoxy (3) and 2,5-dibenzyloxy (4) derivatives. Compounds 3 and 4 were condensed with suitable benzaldehydes to give chalcones 5-10. The thiol group of the chalcones was deprotected by a cleavage of the p-methoxybenzyl protecting group using a new, mild method (silver nitrate in boiling ethanol, 2 h), and the products were cyclized to thioflavanones (15-20). Dehydrogenation of the thioflavanones gave related thioflavones (25-27). Deprotection of methoxy and benzyloxy groups is also described.

  DOI：

  10.1021/jo980586w

文献信息

• [EN] FLAVONOID COMPOUNDS, AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS FLAVONOÏDES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：MCLACHLAN GRANT

  公开号：WO2013020184A9

  公开（公告）日：2013-04-18
• FLAVONOID COMPOUNDS, AND METHODS OF USE THEREOF
  申请人：ARMARON BIO PTY LTD

  公开号：EP2742033B1

  公开（公告）日：2018-09-19
• US20140275156A1
  申请人：——

  公开号：US20140275156A1

  公开（公告）日：2014-09-18
• Synthesis and Reactivity of 5,8-Dihydroxythioflavanone Derivatives
  作者：Marek T. Konieczny、Barbara Horowska、Antoni Kunikowski、Jerzy Konopa、Konstanty Wierzba、Yuji Yamada、Tetsuji Asao

  DOI：10.1021/jo980586w

  日期：1999.1.1

  The synthesis of substituted chalcones, thioflavanones, and thioflavones hydroxylated in both A and B rings is described. Acetoquinone (1) was transformed into 2,5-dihydroxy-6-(p-methoxybenzylmercapto)acetophenone (2) and subsequently into its 2,5-dimethoxy (3) and 2,5-dibenzyloxy (4) derivatives. Compounds 3 and 4 were condensed with suitable benzaldehydes to give chalcones 5-10. The thiol group of the chalcones was deprotected by a cleavage of the p-methoxybenzyl protecting group using a new, mild method (silver nitrate in boiling ethanol, 2 h), and the products were cyclized to thioflavanones (15-20). Dehydrogenation of the thioflavanones gave related thioflavones (25-27). Deprotection of methoxy and benzyloxy groups is also described.