6-amino-5-methoxy-1,2,3-trimethylindole

• 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-amino-5-methoxy-1,2,3-trimethylindole
• 英文别名: 5-methoxy-1,2,3-trimethyl-1H-indol-6-ylamine；6-Amino-5-methoxy-1,2,3-trimethylindole；5-methoxy-1,2,3-trimethylindol-6-amine
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: QMJWZSKIUCTCTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-amino-5-methoxy-1,2,3-trimethylindole 、 草酰乙酸二乙酯 在 溶剂黄146 作用下， 以 苯 为溶剂， 反应 60.0h， 以68%的产率得到diethyl (2-Z)-2-(5-methoxy-1,2,3-trimethyl-1H-indol-6-ylamino)-2-butenedioate
  参考文献：
  名称：

  由取代的6-氨基吲哚和草酰乙酸酯合成吡咯并喹啉

  摘要：

  It was established that the initial condensation of substituted 6-aminoindoles and oxaloacetic ester in boiling benzene with the addition of catalytic amounts of acetic acid takes place exclusively through the carboxyl group of the keto ester with the formation of the corresponding enamines, which successfully undergo thermal cyclization (biphenyl, 280 degrees C) to pyrroloquinolines. Here, irrespective of the nature of substituents at the N-1 and C-5 atoms enamines with a free position 7 are transformed into pyrrolo-[2,3-f]quinolines (structural analogs of vitamin PQQ) while 7-OMe-substituted enamines give pyrrolo[3,2-g]quinolines with linear fusion of the rings.

  DOI：

  10.1007/s10593-008-0111-8

文献信息

• Chloroacetates of Substituted 1H-Indol-5-,6-,7-Ylamines and Their Antimicrobial Activity
  作者：S. A. Yamashkin、I. S. Stepanenko、A. I. Kiryutina、T. N. Platkova

  DOI：10.1007/s11094-024-03047-8

  日期：2024.1

  reaction of substituted 1H-indol-5-, 6-, 7-ylamines with chloroacetic acid; identified based on PMR, UV, and mass spectra; and screened in the laboratory for antimicrobial activity. All the tested compounds could suppress the growth of microorganism test strains at various minimum inhibitory concentrations (MICs). The MIC values were observed to depend on the nature and pattern of substitution on the indole

  由取代的1H-吲哚-5-,6-,7-基胺与氯乙酸反应得到水溶性1H-吲哚-5-,6-,7-基氯乙酸铵；基于 PMR、UV 和质谱进行鉴定；并在实验室进行抗菌活性筛选。所有测试的化合物都能在不同的最低抑制浓度（MIC）下抑制微生物测试菌株的生长。观察到 MIC 值取决于吲哚系统取代的性质和模式。
• The potential use of 6-amino-5-methoxy(methyl)-2,3-dimethyl-and 6-amino-5-methoxy(methyl)-1,2,3-trimethyl-indoles in the synthesis of pyrrolo[2,3-f]quinolines
  作者：S. A. Yamashkin、E. A. Oreshkina、I. S. Romanova、M. A. Yurovskaya

  DOI：10.1007/s10593-006-0051-0

  日期：2006.1
• Synthesis of pyrroloquinolines from substituted 6-aminoindoles and oxaloacetic ester
  作者：S. A. Yamashkin、N. V. Zhukova、I. S. Romanova

  DOI：10.1007/s10593-008-0111-8

  日期：2008.7

  It was established that the initial condensation of substituted 6-aminoindoles and oxaloacetic ester in boiling benzene with the addition of catalytic amounts of acetic acid takes place exclusively through the carboxyl group of the keto ester with the formation of the corresponding enamines, which successfully undergo thermal cyclization (biphenyl, 280 degrees C) to pyrroloquinolines. Here, irrespective of the nature of substituents at the N-1 and C-5 atoms enamines with a free position 7 are transformed into pyrrolo-[2,3-f]quinolines (structural analogs of vitamin PQQ) while 7-OMe-substituted enamines give pyrrolo[3,2-g]quinolines with linear fusion of the rings.