5-methoxyindole-4,7-quinone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-methoxyindole-4,7-quinone
• 英文别名: 5-methoxy-1H-indole-4,7-dione
• 化学式: C₉H₇NO₃
• 分子量: 177.159
• InChiKey: VVHSETXVMNVIMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-甲氧基-1H-吲哚-4-醇 在 salcomine 、 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以58%的产率得到5-methoxyindole-4,7-quinone
  参考文献：
  名称：

  Antimicrobial indolequinones from the mid-intestinal gland of the muricid gastropod Drupella fragum

  摘要：

  Three new indolequinones, 6-merhoxyindole-4,7-quinone (1), 5-methoxyindole-4,7-quinone (2) and 5-methylindole-4,7-quinone (3) were isolated from the mid-intestinal gland of the muricid gastropod Drupella fragum. The structures of 1 and 2 were established by spectroscopic methods and total synthesis, whereas the structure of 3 was elucidated mainly by NMR spectroscopic analyses. Compounds 1 3 exhibited moderate antimicrobial activities against Staphylococcus aureus, Bacillus subtilis, and Escherichia coli with MIC = 6.25 similar to 50 mu g/mL. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00593-6

文献信息

• Iridium-Catalyzed C–H Borylation-Based Synthesis of Natural Indolequinones
  作者：Christy Wang、Jonathan Sperry

  DOI：10.1021/jo300330u

  日期：2012.3.16

  An iridium-catalyzed C-H borylation provides the key step in a short synthesis of two indolequinone natural products. This regioselective C-H functionalization strategy delivers 7-borylindoles that undergo facile oxidation hydrolysis to 7-hydroyindoles and subsequent oxidation to the desired indolequinones, thereby demonstrating a powerful application of the iridium-catalyzed C H borylation reaction. A significant result has arisen from the iridium-catalyzed borylation of N-diethylhydrosilyl-6-methoxyindole; even in the presence of a substituent at C6, the N-hydrosilyl group still directs borylation exclusively into the more sterically hindered C7 position in preference to C2.
• Antimicrobial indolequinones from the mid-intestinal gland of the muricid gastropod Drupella fragum
  作者：Yoshiyasu Fukuyama、Chie Iwatsuki、Mitsuaki Kodama、Masamitsu Ochi、Kumi Kataoka、Kozo Shibata

  DOI：10.1016/s0040-4020(98)00593-6

  日期：1998.8

  Three new indolequinones, 6-merhoxyindole-4,7-quinone (1), 5-methoxyindole-4,7-quinone (2) and 5-methylindole-4,7-quinone (3) were isolated from the mid-intestinal gland of the muricid gastropod Drupella fragum. The structures of 1 and 2 were established by spectroscopic methods and total synthesis, whereas the structure of 3 was elucidated mainly by NMR spectroscopic analyses. Compounds 1 3 exhibited moderate antimicrobial activities against Staphylococcus aureus, Bacillus subtilis, and Escherichia coli with MIC = 6.25 similar to 50 mu g/mL. (C) 1998 Elsevier Science Ltd. All rights reserved.

表征谱图