1,3,5-三羟基-4-异戊二烯氧蒽酮 | 53377-61-0

• 物质功能分类: 天然产物 - 氧杂蒽酮
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 1,3,5-三羟基-4-异戊二烯氧蒽酮
• 中文别名: 1,3,5-三羟基-4-异戊烯基氧杂蒽酮
• 英文名称: 1,3,5-trihydroxy-4-(3-methylbut-2-enyl)-9H-xanthen-9-one
• 英文别名: 1,3,5-trihydroxy-4-prenylxanthone；1,3,6-trihydroxy-4-prenylxanthone；1,3,5-Trihydroxy-4-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one；1,3,5-trihydroxy-4-(3-methylbut-2-enyl)xanthen-9-one
• CAS: 53377-61-0
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: JCHQJCJKSHNCBA-UHFFFAOYSA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  1,3,5-三羟基-4-异戊二烯氧蒽酮 在 氧气 、 tetraphenylporphyrin 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以17%的产率得到6-去氧异巴西红厚壳素
  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
• 作为产物：
  描述：

  2,3-二甲氧基苯甲酸 在 吡啶 、 氢氧化钾 、 三氯化铝 、 草酰氯 、 四甲基氢氧化铵 、 氢碘酸 、 苯酚 作用下， 以 二氯甲烷 为溶剂， 反应 62.0h， 生成 1,3,5-三羟基-4-异戊二烯氧蒽酮
  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

• JPH10203976A
  申请人：——

  公开号：JPH10203976A

  公开（公告）日：1998-08-04
• 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.