3'-benzyloxy-4',5,7-trimethoxy-4-phenyl-2H-1-benzopyran-2-one | 243990-60-5

• 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: 3'-benzyloxy-4',5,7-trimethoxy-4-phenyl-2H-1-benzopyran-2-one
• 英文别名: 4-(3'-benzyloxy-4'-methoxyphenyl)-5,7-dimethoxychromen-2-one；5,7-Dimethoxy-4-(4-methoxy-3-phenylmethoxyphenyl)chromen-2-one
• CAS: 243990-60-5
• 化学式: C₂₅H₂₂O₆
• 分子量: 418.446
• InChiKey: CRCONSCSQWKBHD-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：

  3'-benzyloxy-4',5,7-trimethoxy-4-phenyl-2H-1-benzopyran-2-one 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到3'-hydroxy-4',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
• 作为产物：
  描述：

  2-(苄氧基)-4-溴苯甲醚 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 3'-benzyloxy-4',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 <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.