5-hydroxy-6-methoxy-3-methylisocoumarin | 1396319-52-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 5-hydroxy-6-methoxy-3-methylisocoumarin
• 英文别名: 5-Hydroxy-6-methoxy-3-methylisochromen-1-one；5-hydroxy-6-methoxy-3-methylisochromen-1-one
• CAS: 1396319-52-0
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: IOIJSJONVQBPIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-benzyloxy-6-methoxy-3-methylisocoumarin 在 palladium(II) hydroxide 、 环己烯 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以87%的产率得到5-hydroxy-6-methoxy-3-methylisocoumarin
  参考文献：
  名称：

  Pd(II)-Mediated Cyclization of o-Allylbenzaldehydes in Water: A Novel Synthesis of Isocoumarins

  摘要：

  A novel, concise and efficient synthesis of substituted isocoumarins is disclosed. o-Allylbenzaldehydes prepared from isovanillin were mediated by PdCl2-CuCl2 in water to undergo a domino reaction sequence, including 6-exo-trig cyclization, the addition of water, the elimination of PdHCl, the isomerization of carbon-carbon double bond, the oxidation of hemiacetals with the elimination of PdHCl, and regeneration of PdCl2 in situ to yield a series of new substituted isocoumarins in high yields, in one pot.

  DOI：

  10.1021/ol302256y

文献信息

• Pd(II)-Mediated Cyclization of <i>o</i>-Allylbenzaldehydes in Water: A Novel Synthesis of Isocoumarins
  作者：Po-Yuan Chen、Keng-Shiang Huang、Chin-Chuan Tsai、Tzu-Pin Wang、Eng-Chi Wang

  DOI：10.1021/ol302256y

  日期：2012.9.21

  A novel, concise and efficient synthesis of substituted isocoumarins is disclosed. o-Allylbenzaldehydes prepared from isovanillin were mediated by PdCl2-CuCl2 in water to undergo a domino reaction sequence, including 6-exo-trig cyclization, the addition of water, the elimination of PdHCl, the isomerization of carbon-carbon double bond, the oxidation of hemiacetals with the elimination of PdHCl, and regeneration of PdCl2 in situ to yield a series of new substituted isocoumarins in high yields, in one pot.