6-hydroxy-4-(4-hydroxyphenyl)-7-methoxy-2H-1-benzopyran-2-one | 58115-08-5

• 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: 6-hydroxy-4-(4-hydroxyphenyl)-7-methoxy-2H-1-benzopyran-2-one
• 英文别名: melanettin；6-hydroxy-4-(4-hydroxy-phenyl)-7-methoxy-chromen-2-one；Melannin；6-hydroxy-4-(4-hydroxyphenyl)-7-methoxychromen-2-one
• CAS: 58115-08-5
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: HUGUGFBIYQBLCS-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  233-234°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Methyl 3-[4-methoxy-2,5-bis(methoxymethoxy)phenyl]prop-2-ynoate 、 4-(叔丁基二甲基硅氧基)苯基硼酸 在 copper (I) acetate 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以94%的产率得到6-hydroxy-4-(4-hydroxyphenyl)-7-methoxy-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Synthesis of 4-Arylcoumarins via Cu-Catalyzed Hydroarylation with Arylboronic Acids

  摘要：

  In the presence of 2-4 mol % of CuOAc, methyl phenylpropiolates having a MOM-protected hydroxy group at the ortho position underwent hydroarylation with various arylboronic acids in MeOH at ambient temperature, resulting in the formation of 4-arylcoumarins in high yields after the acidic workup. This method was effectively used for the synthesis of biologically active natural and artificial compounds.

  DOI：

  10.1021/ol802239n

文献信息

• Synthesis of 4-Arylcoumarins via Cu-Catalyzed Hydroarylation with Arylboronic Acids
  作者：Yoshihiko Yamamoto、Naohiro Kirai

  DOI：10.1021/ol802239n

  日期：2008.12.18

  In the presence of 2-4 mol % of CuOAc, methyl phenylpropiolates having a MOM-protected hydroxy group at the ortho position underwent hydroarylation with various arylboronic acids in MeOH at ambient temperature, resulting in the formation of 4-arylcoumarins in high yields after the acidic workup. This method was effectively used for the synthesis of biologically active natural and artificial compounds.