2,5-dihydroxy-6-(p-methoxybenzylmercapto)acetophenone | 187273-93-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-dihydroxy-6-(p-methoxybenzylmercapto)acetophenone
• 英文别名: 1-[3,6-Dihydroxy-2-[(4-methoxyphenyl)methylsulfanyl]phenyl]ethanone
• CAS: 187273-93-4
• 化学式: C₁₆H₁₆O₄S
• 分子量: 304.367
• InChiKey: FCRKUJHDCVAPNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  92.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-dihydroxy-6-(p-methoxybenzylmercapto)acetophenone 在 氢氧化钾 、 四丁基氯化铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 71.5h， 生成 2',3,4,5'-tetrabenzyloxy-6'-(p-methoxybenzylmercapto)chalcone
  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
• 作为产物：
  描述：

  2-乙酰基-1,4-苯醌 、 4-甲氧基苄硫醇 以 乙醇 为溶剂， 反应 0.5h， 以90%的产率得到2,5-dihydroxy-6-(p-methoxybenzylmercapto)acetophenone
  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

• 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.