7-氨基-2-甲基喹啉-3-羧酸甲酯 | 1013629-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 7-氨基-2-甲基喹啉-3-羧酸甲酯
• 英文名称: 7-amino-2-methylquinoline-3-carboxylic acid methyl ester
• 英文别名: Methyl 7-amino-2-methylquinoline-3-carboxylate；methyl 7-amino-2-methylquinoline-3-carboxylate
• CAS: 1013629-22-5
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: CUECTNICHWIVOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-氨基-2-甲基喹啉-3-羧酸甲酯 、 4-甲苯磺酸酐 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以82%的产率得到7-di-p-tosylamino-2-methylquinoline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of new lavendamycin analogues

  摘要：

  Friedlander reaction between methyl acetoacetate and 2,4-diaminobenzaldehyde provided quinoline 11. Subsequent tosylation, reduction, silylation, and then oxidation led to aldehyde 15. The latter was subjected to a Pictet-Spengler reaction with tryptophan methyl ester that yielded product 16, and then desilylation gave the lavendamycin analogue 17. This compound was oxidized by Dess-Martin periodinane, and the cyclized derivative 18 was obtained via a hemiaminal intermediate. The same sequence from 2,4-diamino-5-methoxybenzaldehyde or from (2,4-diaminophenyl)propan-3-one led to compounds 30 and 31, or 40 and 41, respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.12.016
• 作为产物：
  描述：

  2,4-二氨基苯甲醛 、 乙酰乙酸甲酯 在 哌啶 作用下， 以 甲醇 为溶剂， 反应 120.0h， 以76%的产率得到7-氨基-2-甲基喹啉-3-羧酸甲酯
  参考文献：
  名称：

  Synthesis of new lavendamycin analogues

  摘要：

  Friedlander reaction between methyl acetoacetate and 2,4-diaminobenzaldehyde provided quinoline 11. Subsequent tosylation, reduction, silylation, and then oxidation led to aldehyde 15. The latter was subjected to a Pictet-Spengler reaction with tryptophan methyl ester that yielded product 16, and then desilylation gave the lavendamycin analogue 17. This compound was oxidized by Dess-Martin periodinane, and the cyclized derivative 18 was obtained via a hemiaminal intermediate. The same sequence from 2,4-diamino-5-methoxybenzaldehyde or from (2,4-diaminophenyl)propan-3-one led to compounds 30 and 31, or 40 and 41, respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.12.016

文献信息

• Synthesis of new lavendamycin analogues
  作者：Arnaud Nourry、Stéphanie Legoupy、François Huet

  DOI：10.1016/j.tet.2007.12.016

  日期：2008.2

  Friedlander reaction between methyl acetoacetate and 2,4-diaminobenzaldehyde provided quinoline 11. Subsequent tosylation, reduction, silylation, and then oxidation led to aldehyde 15. The latter was subjected to a Pictet-Spengler reaction with tryptophan methyl ester that yielded product 16, and then desilylation gave the lavendamycin analogue 17. This compound was oxidized by Dess-Martin periodinane, and the cyclized derivative 18 was obtained via a hemiaminal intermediate. The same sequence from 2,4-diamino-5-methoxybenzaldehyde or from (2,4-diaminophenyl)propan-3-one led to compounds 30 and 31, or 40 and 41, respectively. (C) 2008 Elsevier Ltd. All rights reserved.