4'-benzyloxy-3',5,7-trimethoxy-4-phenyl-2H-1-benzopyran-2-one | 97746-19-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 4'-benzyloxy-3',5,7-trimethoxy-4-phenyl-2H-1-benzopyran-2-one
• 英文别名: 4-(4'-benzyloxy-3'-methoxyphenyl)-5,7-dimethoxychromen-2-one；5,7,3'-trimethoxy-4'-benzyloxy-4-phenylcoumarin；5,7-Dimethoxy-4-(3-methoxy-4-phenylmethoxyphenyl)chromen-2-one；5,7-dimethoxy-4-(3-methoxy-4-phenylmethoxyphenyl)chromen-2-one
• CAS: 97746-19-5
• 化学式: C₂₅H₂₂O₆
• 分子量: 418.446
• InChiKey: NQLNSHHYYLJZAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4'-benzyloxy-3',5,7-trimethoxy-4-phenyl-2H-1-benzopyran-2-one 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 96.0h， 以57%的产率得到4'-hydroxy-3',5,7-trimethoxy-4-phenyl-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Coutarea hexandra 4-芳基香豆素的合成

  摘要：

  摘要 从 Coutarea hexandra 中分离出的 5,7-二甲氧基-4-芳基香豆素的结构已通过间苯三酚和苯甲酰乙酸乙酯衍生物的 Pechmann 缩合合成得到证实，其羟基被苄基化或亚甲二氧基保护。形成。

  DOI：

  10.1016/s0031-9422(00)81132-2
• 作为产物：
  描述：

  1-(苄氧基)-4-溴-2-甲氧基苯 在 四(三苯基膦)钯 盐酸 、 copper(l) iodide 、 正丁基锂 、 水 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 苯 为溶剂， 反应 22.5h， 生成 4'-benzyloxy-3',5,7-trimethoxy-4-phenyl-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Synthesis of C-Ring Hydroxylated Neoflavonoids by Ligand Coupling Reactions

  摘要：

  Reaction of 4-trifluoromethanesulfonyloxycoumarin derivatives with benzyloxyphenylboronic acid derivatives under modified Suzuki reaction conditions afforded the corresponding neoflavones. Selective debenzylation took place in high yields when the palladium-catalysed hydrogenolysis was performed in the presence of acetic acid.

  DOI：

  10.1080/00397919908086434

文献信息

• Synthesis of 4-arylcoumarins from Coutarea hexandra
  作者：G Monache

  DOI：10.1016/s0031-9422(00)81132-2

  日期：——

  Abstract The structures assigned to the 5,7-dimethoxy-4-arylcoumarins isolated from Coutarea hexandra have been confirmed by synthesis, via Pechmann condensation of phloroglucinol and an ethyl benzoylacetate derivative, the hydroxy groups of which were protected either by benzylation or by methylenedioxy group formation.

  摘要 从 Coutarea hexandra 中分离出的 5,7-二甲氧基-4-芳基香豆素的结构已通过间苯三酚和苯甲酰乙酸乙酯衍生物的 Pechmann 缩合合成得到证实，其羟基被苄基化或亚甲二氧基保护。形成。
• Synthesis of <i>C</i>-Ring Hydroxylated Neoflavonoids by Ligand Coupling Reactions
  作者：Dervilla M.X. Donnelly、Jean-Pierre Finet、Patrick J. Guiry、Martin D. Rea

  DOI：10.1080/00397919908086434

  日期：1999.8.1

  Reaction of 4-trifluoromethanesulfonyloxycoumarin derivatives with benzyloxyphenylboronic acid derivatives under modified Suzuki reaction conditions afforded the corresponding neoflavones. Selective debenzylation took place in high yields when the palladium-catalysed hydrogenolysis was performed in the presence of acetic acid.
• Synthesis and Biological Evaluation of 4-Arylcoumarin Analogues of Combretastatins
  作者：Christian Bailly、Christine Bal、Pascale Barbier、Sébastien Combes、Jean-Pierre Finet、Marie-Paule Hildebrand、Vincent Peyrot、Nicole Wattez

  DOI：10.1021/jm030903d

  日期：2003.12.1

  A series of A-ring polymethoxylated neoflavonoids was prepared by ligand coupling reactions involving either Suzuki or Stille reactions. Cytotoxicity studies indicated a potent activity against a CEM leukemia cell line for the compounds presenting a substitution pattern related to that of combretastatin A-4. The two compounds having a 3'-OH and a 4'-OCH3 substituents on the 4-phenyl B-ring have no effect on human topoisomerases I and II but potently inhibit, in vitro, microtubule assembly. At the cell level, the active compounds were characterized as proapoptotic agents, but they can also trigger cell death via a nonapoptotic pathway.