Ethyl 3-amino-4-(methoxymethyl)-6-methylthieno[2,3-b]pyridine-2-carboxylate | 170885-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: Ethyl 3-amino-4-(methoxymethyl)-6-methylthieno[2,3-b]pyridine-2-carboxylate
• CAS: 170885-35-5
• 化学式: C₁₃H₁₆N₂O₃S
• mdl: MFCD00432390
• 分子量: 280.348
• InChiKey: IHGUDXGXQBPTRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 3-amino-4-(methoxymethyl)-6-methylthieno[2,3-b]pyridine-2-carboxylate 以 溶剂黄146 为溶剂， 反应 9.5h， 生成 N-butyl-4-methoxymethyl-6-methyl-3-(1H-pyrrol-1-yl)thieno[2,3-b]pyridine-2-carboxamide
  参考文献：
  名称：

  3-(1H-pyrrol-1-yl)噻吩并[2,3-b]吡啶的合成与转化

  摘要：

  2,5-二甲氧基四氢呋喃与 3-氨基噻吩并 [2,3-b] 吡啶的反应提供了许多取代的 3-(1H-吡咯-1-基) 噻吩并 [2,3-b] 吡啶。反应的可能性和产物的产率由噻吩并[2,3-b]吡啶2位取代基的特征决定。2-acylazido-3(1H-pyrrol-1-yl)thieno[2,3-b]pyridines 的 Curtius 重排产生 4,5-dihydropyrido[3",2":4,5]thieno[2,3- e]吡咯并[1,2-a]吡嗪-4-酮。4-甲氧基甲基-6-甲基-3-(1H-吡咯-1-基)噻吩并[2,3-b]吡啶-2-羧酸乙酯的分子和晶体结构由X射线衍射分析确定。

  DOI：

  10.1023/b:rucb.0000037855.13096.6e
• 作为产物：
  描述：

  (3-Cyano-4-methoxymethyl-6-methyl-pyridin-2-ylsulfanyl)-acetic acid ethyl ester 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以78%的产率得到Ethyl 3-amino-4-(methoxymethyl)-6-methylthieno[2,3-b]pyridine-2-carboxylate
  参考文献：
  名称：

  Electrochemical synthesis and studies of substituted 2-thiopyridines

  摘要：

  A series of substituted 2-alkyl(aryl-, hetaryl-)thiopyridines was prepared by cathodic electrolysis of thiols in the presence of 2-chloro-3-cyano-4-methoxymethyl-6-methylpyridine or 4-chloro-6-methyl-3-oxo-1 H-furo[3,4-c]pyridine. The reaction of 3-cyano-4-methoxymethyl-6-methyl-2(1H)-thiopyridone with alkyl halides in the presence of KOH is regioselective and leads to S-alkyl derivatives. The advantages of electrosynthesis for the preparation of 2-alkylthiopyridines fused with 2(5H)-furanone and of 3-aminothieno[2,3-b]pyridines is demonstrated.

  DOI：

  10.1007/bf00700178

文献信息

• Cascade Transformations of 3-Amino-2-benzoylthieno[2,3-b]pyridines
  作者：V. K. Vasilin、T. A. Stroganova、N. V. Shitikov、A. V. Bespalov、G. D. Krapivin

  DOI：10.1134/s10703632220505x

  日期：2022.5

  Abstract A new series of thienopyridine derivatives, namely N-(thieno[2,3-b]pyridin-3-yl)aminoalcohols, was obtained by a cascade deacylation/alkylation reaction of 3-aminothieno[2,3-b]pyridine ketones. An alternative approach to the synthesis of these compounds by alkylation of 3-aminothienopyridines unsubstituted at position 2 with diols was proposed.

  摘要 通过3-氨基噻吩并[2,3- b ]吡啶酮的级联脱酰/烷基化反应，得到了一系列新的噻吩并吡啶衍生物，即N- (噻吩并[2,3 - b ]吡啶-3-基)氨基醇。提出了通过用二醇烷基化 2 位未取代的 3-氨基噻吩并吡啶来合成这些化合物的替代方法。
• Synthesis and properties of (thieno[2,3-b]pyridin-3-yl)iminotriphenylphosphoranes. Molecular structure of (2-benzoyl-4-methoxymethyl-6-methylthieno[2,3-b]pyridin-3-yl)iminotriphenylphosphorane
  作者：E. A. Kaigorodova、V. K. Vasilin、M. M. Lipunov、V. E. Zavodnik、G. D. Krapivin

  DOI：10.1007/s10593-005-0104-9

  日期：2004.12
• Synthesis and reactivity of 3-amino-9-methoxymethyl-7-methyl-3,4-dihydropyrido-[3′,2′:4,5]thieno[3,2-d]pyrimidin-4-ones
  作者：E. S. Kostenko、M. M. Lipunov、E. A. Kaigorodova、L. D. Konyushkin

  DOI：10.1007/s10593-007-0226-3

  日期：2007.11
• Electrochemical synthesis and studies of substituted 2-thiopyridines
  作者：E. A. Kaigorodova、L. D. Konyushkin、M. E. Niyazymbetov、S. N. Kvak、V. N. Zaplishny、V. P. Litvinov

  DOI：10.1007/bf00700178

  日期：1994.12

  A series of substituted 2-alkyl(aryl-, hetaryl-)thiopyridines was prepared by cathodic electrolysis of thiols in the presence of 2-chloro-3-cyano-4-methoxymethyl-6-methylpyridine or 4-chloro-6-methyl-3-oxo-1 H-furo[3,4-c]pyridine. The reaction of 3-cyano-4-methoxymethyl-6-methyl-2(1H)-thiopyridone with alkyl halides in the presence of KOH is regioselective and leads to S-alkyl derivatives. The advantages of electrosynthesis for the preparation of 2-alkylthiopyridines fused with 2(5H)-furanone and of 3-aminothieno[2,3-b]pyridines is demonstrated.
• Synthesis and transformations of 3-(1H-pyrrol-1-yl)thieno[2,3-b]pyridines
  作者：E. A. Kaigorodova、A. A. Osipova、L. D. Konyushkin、G. D. Krapivin

  DOI：10.1023/b:rucb.0000037855.13096.6e

  日期：2004.4

  5-dimethoxytetrahydrofuran with 3-aminothieno[2,3-b]pyridines afford a number of substituted 3-(1H-pyrrol-1-yl)thieno[2,3-b]pyridines. The possibility of the reaction and the yield of the product are determined by the character of a substituent in position 2 of thieno[2,3-b]pyridine. The Curtius rearrangement of 2-acylazido-3(1H-pyrrol-1-yl)thieno[2,3-b]pyridines yields 4,5-dihydropyrido[3",2":4,5]thieno[2

  2,5-二甲氧基四氢呋喃与 3-氨基噻吩并 [2,3-b] 吡啶的反应提供了许多取代的 3-(1H-吡咯-1-基) 噻吩并 [2,3-b] 吡啶。反应的可能性和产物的产率由噻吩并[2,3-b]吡啶2位取代基的特征决定。2-acylazido-3(1H-pyrrol-1-yl)thieno[2,3-b]pyridines 的 Curtius 重排产生 4,5-dihydropyrido[3",2":4,5]thieno[2,3- e]吡咯并[1,2-a]吡嗪-4-酮。4-甲氧基甲基-6-甲基-3-(1H-吡咯-1-基)噻吩并[2,3-b]吡啶-2-羧酸乙酯的分子和晶体结构由X射线衍射分析确定。