1,3,5,6-tetrahydroxy-2-prenylxanthone | 5490-48-2

• 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: 1,3,5,6-tetrahydroxy-2-prenylxanthone
• 英文别名: 9H-Xanthen-9-one, 1,3,5,6-tetrahydroxy-2-(3-methyl-2-butenyl)-；1,3,5,6-tetrahydroxy-2-(3-methylbut-2-enyl)xanthen-9-one
• CAS: 5490-48-2
• 化学式: C₁₈H₁₆O₆
• 分子量: 328.321
• InChiKey: NPQLJYVRPMRCAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 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：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3,5,6-tetrahydroxy-2-prenylxanthone 、 乙酸酐 在 吡啶 作用下， 反应 24.0h， 以56%的产率得到1-Hydroxy-2-(3,3-dimethylallyl)-3,5,6-triacetylxanthone
  参考文献：
  名称：

  Antifungal Xanthones from Calophyllum brasiliensis Heartwood

  摘要：

  The heartwood of the tropical tree Calophyllum brasiliensis is known to be highly resistant to fungi and termites. To determine whether resistance to wood-rotting fungi could be caused by bioactive secondary metabolites, a chemical and biological study was carried out. Hexane, acetone, methanol, and water extracts were prepared. The yield of the extracts ranged from 0.04% (hexane) to 4.81% (acetone). Methanol, acetone, and water extracts (5 mg/ml = 0.5%) inhibited the mycelial growth of the brown rot fungus Postia placenta by 83%, 59%, and 21%, respectively. Chromatographic separation of the acetone and methanol extracts afforded five prenylated xanthones: 6-desoxyjacareubin (I), 1,5-dihydroxy-2-(3,3-dimethylallyl)-3-methoxy-xanthone (II), jacareubin (III) and 1,3,5-trihydroxy-2-(3,3-dimethylallyl)-xanthone (IV) and 1,3,5,6-tetrahydroxy-2-(3,3-dimethylallyl)-xanthone (V). Xanthones III, IV, and especially V, were the most abundant constituents of both extracts and inhibited at 0.25 mg/ml the mycelial growth of P. placenta. Inhibitory activity ranged from 55.5% (V) to 68.8% (III and IV mixture). Acetylation of xanthones did not induce a sharp change in the extent of fungistasis compared with parent compounds. The above results suggest that C. brasiliensis xanthones actually play a defensive role against wood decay fungi.

  DOI：

  10.1023/b:joec.0000006459.88330.61

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS HYDROXY-ARYLE ORTHO-ALLYLÉS
  申请人：UNIV MCMASTER

  公开号：WO2021237371A1

  公开（公告）日：2021-12-02

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

  本申请描述了一种制备邻烯丙基羟基芳基化合物的方法，例如通过在非质子溶剂中，在氧化铝和铝烷氧化物中选择的铝化合物存在下，将烯丙醇与羟基芳基化合物反应，其中羟基芳基化合物中至少有一个碳原子位于羟基的邻位且未被取代。本申请还包括化合物的化学式（I）。
• PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
  申请人：McMaster University

  公开号：US20210380513A1

  公开（公告）日：2021-12-09

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).
• Antifungal Xanthones from Calophyllum brasiliensis Heartwood
  作者：Ricardo Reyes-Chilpa、Manuel Jimenez-Estrada、Elizabeth Estrada-Muñiz

  DOI：10.1023/b:joec.0000006459.88330.61

  日期：1997.7

  The heartwood of the tropical tree Calophyllum brasiliensis is known to be highly resistant to fungi and termites. To determine whether resistance to wood-rotting fungi could be caused by bioactive secondary metabolites, a chemical and biological study was carried out. Hexane, acetone, methanol, and water extracts were prepared. The yield of the extracts ranged from 0.04% (hexane) to 4.81% (acetone). Methanol, acetone, and water extracts (5 mg/ml = 0.5%) inhibited the mycelial growth of the brown rot fungus Postia placenta by 83%, 59%, and 21%, respectively. Chromatographic separation of the acetone and methanol extracts afforded five prenylated xanthones: 6-desoxyjacareubin (I), 1,5-dihydroxy-2-(3,3-dimethylallyl)-3-methoxy-xanthone (II), jacareubin (III) and 1,3,5-trihydroxy-2-(3,3-dimethylallyl)-xanthone (IV) and 1,3,5,6-tetrahydroxy-2-(3,3-dimethylallyl)-xanthone (V). Xanthones III, IV, and especially V, were the most abundant constituents of both extracts and inhibited at 0.25 mg/ml the mycelial growth of P. placenta. Inhibitory activity ranged from 55.5% (V) to 68.8% (III and IV mixture). Acetylation of xanthones did not induce a sharp change in the extent of fungistasis compared with parent compounds. The above results suggest that C. brasiliensis xanthones actually play a defensive role against wood decay fungi.