disparinol A

• 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: disparinol A
• 英文别名: 5,7-dihydroxy-8-(2-hydroxy-3-methylbut-3-enyl)-6-(3-methylbutanoyl)-4-phenylchromen-2-one
• 化学式: C₂₅H₂₆O₆
• 分子量: 422.478
• InChiKey: IQMQJKCHMGXLEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-苯基-5,7-二羟基-6-(3-甲基丁酰基)-8-(3-甲基-2-丁烯基)-2H-1-苯并吡喃-2-酮 在 氧气 、 tetraphenylporphyrin 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以60%的产率得到disparinol A
  参考文献：
  名称：

  Synthesis of 2-hydroxy-3-methylbut-3-enyl substituted coumarins and xanthones as natural products. Application of the Schenck ene reaction of singlet oxygen with ortho-prenylphenol precursors

  摘要：

  Application of our original photooxidation-reduction methodology to prenylated dihydroxycoumarin and trihydroxyxanthone compounds led to the corresponding ortho-(2-hydroxy-3-methylbut-3-enyl)phenol derivatives with yields ranging from 8 to 65%. In most of the reported experiments, the oxidation products distribution, after the photooxygenation step, was controlled by the competition between the large group effect and the stabilising phenolic assistance effect. We also showed that ortho-(3-hydroxy-3-methylbut-1-enyl)phenol derivatives could be considered as biogenetic precursors of 2,2-dimethylbenzopyranic structures. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.033

文献信息

• Four New 4-Phenylcoumarins from Calophyllum dispar. Isolation and Hemisynthesis
  作者：Pascal Richomme、David Guilet、Cécile Morel、Nathalie Noyer、Maryse Cornec、Denis Séraphin、Christian Wiart、A. Hamid A. Hadi、Thierry Sévenet、Jean Bruneton

  DOI：10.3987/com-98-8338

  日期：——
• Synthesis of 2-hydroxy-3-methylbut-3-enyl substituted coumarins and xanthones as natural products. Application of the Schenck ene reaction of singlet oxygen with ortho-prenylphenol precursors
  作者：Jean-Jacques Helesbeux、Olivier Duval、Caroline Dartiguelongue、Denis Séraphin、Jean-Michel Oger、Pascal Richomme

  DOI：10.1016/j.tet.2004.01.033

  日期：2004.3

  Application of our original photooxidation-reduction methodology to prenylated dihydroxycoumarin and trihydroxyxanthone compounds led to the corresponding ortho-(2-hydroxy-3-methylbut-3-enyl)phenol derivatives with yields ranging from 8 to 65%. In most of the reported experiments, the oxidation products distribution, after the photooxygenation step, was controlled by the competition between the large group effect and the stabilising phenolic assistance effect. We also showed that ortho-(3-hydroxy-3-methylbut-1-enyl)phenol derivatives could be considered as biogenetic precursors of 2,2-dimethylbenzopyranic structures. (C) 2004 Elsevier Ltd. All rights reserved.