2-hydroxy-1,7-dimethoxy-9H-xanthen-9-one

• 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-1,7-dimethoxy-9H-xanthen-9-one
• 英文别名: 2-hydroxyl-1,7-dimethoxyl-xanthone；1,7-dimethoxy-2-hydroxyxanthone；2-hydroxy-1,7-dimethoxyxanthone；2-hydroxy-1,7-dimethoxyxanthen-9-one
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: PIGYJVNDGBCMES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-(benzyloxy)-2-formylphenyl ethyl carbonate 在 吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 三氟甲磺酸酐 、 双氧水 、 溴 、 potassium carbonate 、 potassium bromide 、 copper(II) oxide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 56.0h， 生成 2-hydroxy-1,7-dimethoxy-9H-xanthen-9-one
  参考文献：
  名称：

  Synthesis of 1,7-dimethoxy-2-hydroxyxanthone, a natural product with potential activity on erectile dysfunction

  摘要：

  The natural product, 1,7-dimethoxy-2-hydroxyxanthone (1), isolated from Securidaca inappendiculate Hassk, has a potential in the treatment of erectile dysfunction due to its significant relaxation activity on rabbit Corpus cavernosum. However, the isolation of compound 1 is problematic because of its high similarity in structure to its analogs. In this paper, the first synthesis of 1 was reported featuring two key reactions: a copper-catalyzed coupling reaction and an intramolecular cyclization. (C) 2013 De-Sheng Mei, Wen-Hu Duan. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.03.038

文献信息

• Synthesis of 1,7-dimethoxy-2-hydroxyxanthone, a natural product with potential activity on erectile dysfunction
  作者：Wen-Jing Liu、De-Sheng Mei、Wen-Hu Duan

  DOI：10.1016/j.cclet.2013.03.038

  日期：2013.6

  The natural product, 1,7-dimethoxy-2-hydroxyxanthone (1), isolated from Securidaca inappendiculate Hassk, has a potential in the treatment of erectile dysfunction due to its significant relaxation activity on rabbit Corpus cavernosum. However, the isolation of compound 1 is problematic because of its high similarity in structure to its analogs. In this paper, the first synthesis of 1 was reported featuring two key reactions: a copper-catalyzed coupling reaction and an intramolecular cyclization. (C) 2013 De-Sheng Mei, Wen-Hu Duan. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.