2-hydroxy-6-methyl-8-methoxy-9-oxo-9H-xanthene-1-carboxylic acid

• 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: 2-hydroxy-6-methyl-8-methoxy-9-oxo-9H-xanthene-1-carboxylic acid
• 英文别名: 2-hydroxy-8-methoxy-6-methyl-9-oxoxanthene-1-carboxylic acid
• 化学式: C₁₆H₁₂O₆
• 分子量: 300.268
• InChiKey: BQOVQGSBHRLTFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 2-hydroxy-6-methyl-8-methoxy-9-oxo-9H-xanthene-1-carboxylic acid 以 甲醇 、 乙醚 为溶剂， 反应 1.0h， 以98%的产率得到2,8-dimethoxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Xanthones from a microfungus of the genus Xylaria

  摘要：

  Chemical investigations of a microfungus Xylaria sp. isolated from the Australian rainforest tree Glochidion ferdinandi have afforded two new natural products, 2-hydroxy-6-methyl-8-methoxy-9-oxo-9H-xanthene-1-carboxylic acid (1) and 2-hydroxy-6hydroxymethyl-8-methoxy-9-oxo-9H-xanthene-1-carboxylic acid (2). Compound 1 has previously been synthesised but only partially characterised. Methylation of 1 using diazomethane afforded the crystalline compound 2,8-dimethoxy-6-methyl-9-oxo9H-xanthene-1-carboxylic acid methyl ester (3), whose structure was determined by single crystal X-ray analysis. This paper reports the full spectroscopic characterisation of compounds 1-3 by NMR, UV, IR and MS data. All compounds were inactive in a brine shrimp lethality assay and several antimicrobial screens. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2004.07.019

文献信息

• Xanthones from a microfungus of the genus Xylaria
  作者：Peter C. Healy、Ailsa Hocking、Nai Tran-Dinh、John I. Pitt、Roger G. Shivas、Jennifer K. Mitchell、Mike Kotiw、Rohan A. Davis

  DOI：10.1016/j.phytochem.2004.07.019

  日期：2004.8

  Chemical investigations of a microfungus Xylaria sp. isolated from the Australian rainforest tree Glochidion ferdinandi have afforded two new natural products, 2-hydroxy-6-methyl-8-methoxy-9-oxo-9H-xanthene-1-carboxylic acid (1) and 2-hydroxy-6hydroxymethyl-8-methoxy-9-oxo-9H-xanthene-1-carboxylic acid (2). Compound 1 has previously been synthesised but only partially characterised. Methylation of 1 using diazomethane afforded the crystalline compound 2,8-dimethoxy-6-methyl-9-oxo9H-xanthene-1-carboxylic acid methyl ester (3), whose structure was determined by single crystal X-ray analysis. This paper reports the full spectroscopic characterisation of compounds 1-3 by NMR, UV, IR and MS data. All compounds were inactive in a brine shrimp lethality assay and several antimicrobial screens. (C) 2004 Elsevier Ltd. All rights reserved.