1,4-bis(2-n-butylamino-4-oxopyrazino[2',3':4,5]thieno[3,2-d]pyrimidin-3(4H)-yl)benzene

• 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: 1,4-bis(2-n-butylamino-4-oxopyrazino[2',3':4,5]thieno[3,2-d]pyrimidin-3(4H)-yl)benzene
• 英文别名: 4-(Butylamino)-5-[4-[4-(butylamino)-6-oxo-8-thia-3,5,10,13-tetrazatricyclo[7.4.0.02,7]trideca-1(13),2(7),3,9,11-pentaen-5-yl]phenyl]-8-thia-3,5,10,13-tetrazatricyclo[7.4.0.02,7]trideca-1(13),2(7),3,9,11-pentaen-6-one
• 化学式: C₃₀H₂₈N₁₀O₂S₂
• 分子量: 624.75
• InChiKey: AVXYSKXRBPQOIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  197
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  C₂₆H₁₈N₈O₄S₂ 在 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 7.0h， 生成 1,4-bis(2-n-butylamino-4-oxopyrazino[2',3':4,5]thieno[3,2-d]pyrimidin-3(4H)-yl)benzene
  参考文献：
  名称：

  Efficient one-pot preparation of bis(pyrazino[2′,3′:4,5]thieno[3,2-d]pyrimidin-4-yl)benzenes based on an aza–Wittig/mediated annulation strategy

  摘要：

  Aza-Wittig mediated annulation provides a highly facile and straightforward one-pot strategy for the synthesis of bis(pyrazino[2',3':4,5]thieno[3,2-d]pyrimidin-4-yl)benzenes 5 and 7. A tandem aza-Wittig reaction of iminophosphorane 2 with 1,4- or 1,3-phenylene diisocyanate, followed by intramolecular heteroconjugate addition annulation after addition of a nucleophilic reagent (amine, phenol, thiophenol or ROH), in presence of catalytic K2CO3 Or NaOR, gives selectively the functionalized bis(pyrazinothienopyrimidinones) 5 and 7. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.049

文献信息

• An efficient one-pot three-step domino synthesis of substituted bis(pyrazino[2′,3′:4,5]thieno[3,2-d]pyrimidin-4(3H)-ones)
  作者：Gerardo Blanco、Antonio Fernández-Mato、José M. Quintela、Carlos Peinador

  DOI：10.1016/j.tet.2008.09.067

  日期：2008.12

  A convenient and efficient one-pot three-step domino approach to bis(pyrazinothienopyrimidinones) from ethyl 3-(triphenylphosphoranylideneamino)-thieno[2,3-b]pyrazine-6-carboxylate 1 has been developed. In this method, treatment of phosphazene 1 with a mixture of isocyanates, nitrogen, sulfur, and oxygen bis(nucleophiles) and K2CO3 in refluxing THF regioselectively furnishes the corresponding bis (pyrazino[2',3':4,5]thieno[3,2-d]pyrimid in-4(3H)-ones) in satisfactory to good yields. This methodology is highly versatile and efficient for the generation of these functionalized bis(triheterocyclic) compounds that are not readily available by other synthetic methods. (C) 2008 Elsevier Ltd. All rights reserved.
• Efficient one-pot preparation of bis(pyrazino[2′,3′:4,5]thieno[3,2-d]pyrimidin-4-yl)benzenes based on an aza–Wittig/mediated annulation strategy
  作者：Gerardo Blanco、José M. Quintela、Carlos Peinador

  DOI：10.1016/j.tet.2006.12.049

  日期：2007.2

  Aza-Wittig mediated annulation provides a highly facile and straightforward one-pot strategy for the synthesis of bis(pyrazino[2',3':4,5]thieno[3,2-d]pyrimidin-4-yl)benzenes 5 and 7. A tandem aza-Wittig reaction of iminophosphorane 2 with 1,4- or 1,3-phenylene diisocyanate, followed by intramolecular heteroconjugate addition annulation after addition of a nucleophilic reagent (amine, phenol, thiophenol or ROH), in presence of catalytic K2CO3 Or NaOR, gives selectively the functionalized bis(pyrazinothienopyrimidinones) 5 and 7. (c) 2006 Elsevier Ltd. All rights reserved.