2,5-dibenzyloxy-6-(p-methoxybenzylmercapto)acetophenone | 187273-95-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-dibenzyloxy-6-(p-methoxybenzylmercapto)acetophenone
• 英文别名: 1-[2-[(4-Methoxyphenyl)methylsulfanyl]-3,6-bis(phenylmethoxy)phenyl]ethanone
• CAS: 187273-95-6
• 化学式: C₃₀H₂₈O₄S
• 分子量: 484.616
• InChiKey: SZBPYDOFOQPYSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-dibenzyloxy-6-(p-methoxybenzylmercapto)acetophenone 在 氢氧化钾 、 四丁基氯化铵 、 十六烷基三甲基溴化铵 、 对甲苯磺酸 、 silver nitrate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 74.0h， 生成 3',4',5,8-tetrabenzyloxythioflavanone-1,1-dioxide
  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 在 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 2.0h， 生成 2,5-dibenzyloxy-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.