1,3,5-trihydroxy-2-(2-hydroxy-3-methylbut-3-enyl)-9H-xanthen-9-one | 581101-18-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1,3,5-trihydroxy-2-(2-hydroxy-3-methylbut-3-enyl)-9H-xanthen-9-one
• 英文别名: caledol；9H-Xanthen-9-one, 1,3,5-trihydroxy-2-(2-hydroxy-3-methyl-3-butenyl)-；1,3,5-trihydroxy-2-(2-hydroxy-3-methylbut-3-enyl)xanthen-9-one
• CAS: 581101-18-0
• 化学式: C₁₈H₁₆O₆
• 分子量: 328.321
• InChiKey: LGHOTBXEERKYDS-UHFFFAOYSA-N

物化性质

• 沸点：
  609.3±55.0 °C(Predicted)
• 密度：
  1.465±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Rubraxanthone 在 氧气 、 tetraphenylporphyrin 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以63%的产率得到1,3,5-trihydroxy-2-(2-hydroxy-3-methylbut-3-enyl)-9H-xanthen-9-one
  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

• 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.