3',4'-dibenzyloxy-5,8-dimethoxythioflavanone | 220468-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫铬烷
• 英文名称: 3',4'-dibenzyloxy-5,8-dimethoxythioflavanone
• 英文别名: 2-[3,4-Bis(phenylmethoxy)phenyl]-5,8-dimethoxy-2,3-dihydrothiochromen-4-one
• CAS: 220468-27-9
• 化学式: C₃₁H₂₈O₅S
• 分子量: 512.626
• InChiKey: UVSDGSLANJNHOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3',4'-dibenzyloxy-5,8-dimethoxythioflavanone 在 BF₃(methanethiol) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以59%的产率得到3',4',5,8-tetrahydroxythioflavanone
  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：

  3,4-二苄氧基苯甲醛 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 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 73.0h， 生成 3',4'-dibenzyloxy-5,8-dimethoxythioflavanone
  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