ethyl 2-(ethoxymethyl)-4-oxo-3-(2-propynyl)-3,5,6,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7(4H)-carboxylate | 1221682-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: ethyl 2-(ethoxymethyl)-4-oxo-3-(2-propynyl)-3,5,6,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7(4H)-carboxylate
• 英文别名: Ethyl 5-(ethoxymethyl)-3-oxo-4-prop-2-ynyl-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7),5-triene-11-carboxylate；ethyl 5-(ethoxymethyl)-3-oxo-4-prop-2-ynyl-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7),5-triene-11-carboxylate
• CAS: 1221682-44-5
• 化学式: C₁₈H₂₁N₃O₄S
• 分子量: 375.448
• InChiKey: NBSGXCUVYMQWIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  疊氮乙酸 、 ethyl 2-(ethoxymethyl)-4-oxo-3-(2-propynyl)-3,5,6,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7(4H)-carboxylate 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 以86%的产率得到2-(4-([7-(ethoxycarbonyl)-2-(ethoxymethyl)-4-oxo-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-3(4H)-yl]methyl)-1H-1,2,3-triazol-1-yl)acetic acid
  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：

  ethyl 2-(ethoxymethyl)-4-oxo-3,5,6,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7(4H)-carboxylate 、 3-溴丙炔 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以89%的产率得到ethyl 2-(ethoxymethyl)-4-oxo-3-(2-propynyl)-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