ethyl 3-(aminocarbonyl)-2-[(2-chloroacetyl)amino]-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate | 1221682-40-1

• 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-(aminocarbonyl)-2-[(2-chloroacetyl)amino]-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate
• 英文别名: ethyl 3-carbamoyl-2-[(2-chloroacetyl)amino]-5,7-dihydro-4H-thieno[2,3-c]pyridine-6-carboxylate
• CAS: 1221682-40-1
• 化学式: C₁₃H₁₆ClN₃O₄S
• 分子量: 345.807
• InChiKey: JNAZMFROBONVMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-(aminocarbonyl)-2-[(2-chloroacetyl)amino]-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以87%的产率得到ethyl 2-(chloromethyl)-4-oxo-3,5,6,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7(4H)-carboxylate
  参考文献：
  名称：

  A convenient method for constructing novel tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]-pyrimidinones-carbohydrate and amino acid conjugates via copper(I)-catalyzed alkyne-azide ‘Click Chemistry’

  摘要：

  Novel conjugates of tetrahydropyridothienopyrimidones and carbohydrates of amino acids linked by 1,2,3-triazoles were synthesized After establishing the tetrahydropyridothienopyrimidones ring system by ring closure, propargyl groups were introduced by N-alkylation Cu-catalyzed cycloaddition of the propargyl products with azido group containing hexoses or amino acids gives the corresponding 1,2,3-triazoles in high yields This methodology also allowed attaching two carbohydrate molecules to the tetrahydropyridothienopyrimidone core Interesting dependence of the regioselectivity of the N-propargylation of the pyrimidone ring oil the exocyclic substituent found adjacent to the pyrimidine-N-atom was observed A remarkable case of a non-catalyzed intramolecular [3+2]-cycloaddition of an alkyne with ail azide to a 1,2,3-triazole was observed. which occurred in the solid state at it or below (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.01.071
• 作为产物：
  描述：

  2-氨基-3-(氨基羰基)-4,7-二氢噻吩并[2,3-C]吡啶-6(5H)-甲酸乙酯 、 氯乙酰氯 以 二氯甲烷 为溶剂， 以76%的产率得到ethyl 3-(aminocarbonyl)-2-[(2-chloroacetyl)amino]-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate
  参考文献：
  名称：

  A convenient method for constructing novel tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]-pyrimidinones-carbohydrate and amino acid conjugates via copper(I)-catalyzed alkyne-azide ‘Click Chemistry’

  摘要：

  Novel conjugates of tetrahydropyridothienopyrimidones and carbohydrates of amino acids linked by 1,2,3-triazoles were synthesized After establishing the tetrahydropyridothienopyrimidones ring system by ring closure, propargyl groups were introduced by N-alkylation Cu-catalyzed cycloaddition of the propargyl products with azido group containing hexoses or amino acids gives the corresponding 1,2,3-triazoles in high yields This methodology also allowed attaching two carbohydrate molecules to the tetrahydropyridothienopyrimidone core Interesting dependence of the regioselectivity of the N-propargylation of the pyrimidone ring oil the exocyclic substituent found adjacent to the pyrimidine-N-atom was observed A remarkable case of a non-catalyzed intramolecular [3+2]-cycloaddition of an alkyne with ail azide to a 1,2,3-triazole was observed. which occurred in the solid state at it or below (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.01.071

文献信息

• Novel nanoscaled molecular rods consisting of seven annulated heterocycles as scaffold for multiple sugar units
  作者：Mohamed A. Ameen、Sebastian Karsten、Robert Fenger、Jürgen Liebscher

  DOI：10.1016/j.tetlet.2010.06.040

  日期：2010.8

  A nanoscaled molecular rod consisting of a novel heterocyclic system of seven annulated heterocycles was obtained in a straight forward way It served as a scaffold for eight functionalized 1,2,3-triazoles established by multiple alkyne-azide click reaction affording nanoobjects which are surrounded by carbohydrate shells (c) 2010 Elsevier Ltd All rights reserved.
• A convenient method for constructing novel tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]-pyrimidinones-carbohydrate and amino acid conjugates via copper(I)-catalyzed alkyne-azide ‘Click Chemistry’
  作者：Mohamed A. Ameen、Sebastian Karsten、Jürgen Liebscher

  DOI：10.1016/j.tet.2010.01.071

  日期：2010.3

  Novel conjugates of tetrahydropyridothienopyrimidones and carbohydrates of amino acids linked by 1,2,3-triazoles were synthesized After establishing the tetrahydropyridothienopyrimidones ring system by ring closure, propargyl groups were introduced by N-alkylation Cu-catalyzed cycloaddition of the propargyl products with azido group containing hexoses or amino acids gives the corresponding 1,2,3-triazoles in high yields This methodology also allowed attaching two carbohydrate molecules to the tetrahydropyridothienopyrimidone core Interesting dependence of the regioselectivity of the N-propargylation of the pyrimidone ring oil the exocyclic substituent found adjacent to the pyrimidine-N-atom was observed A remarkable case of a non-catalyzed intramolecular [3+2]-cycloaddition of an alkyne with ail azide to a 1,2,3-triazole was observed. which occurred in the solid state at it or below (C) 2010 Elsevier Ltd All rights reserved