6-methoxy-1H-indole-4,7-dione | 137542-70-2

• 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: 6-methoxy-1H-indole-4,7-dione
• 英文别名: 6-methoxyindole-4,7-quinone
• CAS: 137542-70-2
• 化学式: C₉H₇NO₃
• 分子量: 177.159
• InChiKey: UVIWOIATAPBTCZ-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

• 作为反应物：
  描述：

  6-methoxy-1H-indole-4,7-dione 、 苄胺 以 甲醇 为溶剂， 反应 72.0h， 以35%的产率得到6-(N'-Benzylamino)indole-4,7-quinone
  参考文献：
  名称：

  Regioselective Amination of Indole-4,7-quinones

  摘要：

  DOI：

  10.1021/jo00116a049
• 作为产物：
  描述：

  6-甲氧基吲哚 在 salcomine 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 双氧水 、 氧气 、 sodium acetate 、 联硼酸频那醇酯 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 34.17h， 生成 6-methoxy-1H-indole-4,7-dione
  参考文献：
  名称：

  Iridium-Catalyzed C–H Borylation-Based Synthesis of Natural Indolequinones

  摘要：

  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.

  DOI：

  10.1021/jo300330u

文献信息

• Azide-Mediated Detosylation of <i>N</i>-Tosylpyrroloiminoquinones and <i>N</i>-Tosylindole-4,7-quinones
  作者：Sadanandan Velu、Swayamprabha Patel、Dwayaja Nadkarni、Srinivasan Murugesan、Jason King

  DOI：10.1055/s-0028-1083570

  日期：——

  The utility of NaN3 as a reagent for the detosylation of N-tosylpyrroloiminoquinones and N-tosylindole-4,7-quinones is described. The NaN3-mediated detosylation is carried out in polar aprotic solvents such as DMF and DMSO. The reaction occurs under neutral, mild conditions and results in good to excellent yields of the detosylated quinones.

  NaN3作为N-甲苯磺酰吡咯并咪诺喹啉和N-甲苯磺酰吲哚-4,7-喹啉脱甲苯磺酰化反应试剂的实用性已经得到了描述。在极性质子惰性溶剂如DMF和DMSO中进行NaN3介导的脱甲苯磺酰化反应。该反应在温和中性条件下进行，并能获得较好的至优异的脱甲苯磺酰化喹啉产率。
• A novel entry to 4,7-indoloquinones via the Fremy's salt oxidative degradation of 4-formyl-7-hydroxyindoles
  作者：Jose M. Saa、Catalina Marti、Angel Garcia-Raso

  DOI：10.1021/jo00028a035

  日期：1992.1

  A novel synthetic approach toward 4-formyl-7-hydroxyindoles and 4,7-indoloquinones is described. Basically, two major operations need to be carried out, namely: (1) ozonization of the appropriately protected 4-amino-5-hydroxyindenes leading eventually to 4-formyl-7-hydroxyindoles and (2) Fremy's salt promoted oxidative degradation of the later compounds to the desired 4,7-indoloquinones. A formal synthesis of PDE I and PDE II has been achieved.
• 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.
• Regioselective Amination of Indole-4,7-quinones
  作者：Yvette A. Jackson、Adil D. Billimoria、Eyyani V. Sadanandan、Michael P. Cava

  DOI：10.1021/jo00116a049

  日期：1995.6
• 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.

表征谱图