2,7-bis[4-(methylsulfanyl)phenoxy]-3,6-diphenyl-3,4,5,6-tetrahydrothieno[2,3-d:5,4-d']dipyrimidine-4,5-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,7-bis[4-(methylsulfanyl)phenoxy]-3,6-diphenyl-3,4,5,6-tetrahydrothieno[2,3-d:5,4-d']dipyrimidine-4,5-dione
• 英文别名: 5,11-Bis(4-methylsulfanylphenoxy)-4,12-diphenyl-8-thia-4,6,10,12-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),5,10-tetraene-3,13-dione
• 化学式: C₃₄H₂₄N₄O₄S₃
• 分子量: 648.787
• InChiKey: PUBCKASVEIOHFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  45
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  163
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,5-二氨基-3,4-噻吩二羧酸二乙酯 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 六氯乙烷 、 乙腈 为溶剂， 反应 4.0h， 生成 2,7-bis[4-(methylsulfanyl)phenoxy]-3,6-diphenyl-3,4,5,6-tetrahydrothieno[2,3-d:5,4-d']dipyrimidine-4,5-dione
  参考文献：
  名称：

  Application of Bis(iminophosphorane) in Heterocyclic Synthesis:  New Entries to Symmetrically or Unsymmetrically Substituted Thieno[2,3-d:5,4-d‘]dipyrimidine-4,5(3H,6H)-diones

  摘要：

  The bis(carbodiimides) 4, obtained from bis-aza-Wittig reactions of bis(iminophosphorane) 3 with 2 equiv of aromatic isocyanates, were reacted with secondary amine to give symmetrically substituted 2,7-diaminothieno[2,3-d:5,4-d']dipyrimidine-4,5(3H,6H)-dione 6 in the presence of a catalytic amount of EtO-Na+ Reactions of 4 with phenols or ROH in the presence of a catalytic amount of potassium carbonate or RO-Na+ gave symmetrically substituted 2,7-diaryl(alkyl)oxythieno[2,3-d:5,4-d']dipyrimidine-4,5(3H,6H)-diones 6 in satisfactory yields. However, iminophosphoranes 9 were obtained via reaction of bis(iminophosphorane) 3 with 1 equiv of aromatic isocyanate and subsequent reaction with an amine in the presence of a catalytic amount of EtO-Na+. Further reaction of iminophosphoranes 9 with aromatic isocyanates and various nucleophile generated unsymmetrically substituted thieno[2,3-d:5,4-d']dipyrimidine-4,5(3H,6H)-diones 12 in good yields.

  DOI：

  10.1021/jo048691v

文献信息

• Application of Bis(iminophosphorane) in Heterocyclic Synthesis:  New Entries to Symmetrically or Unsymmetrically Substituted Thieno[2,3-<i>d</i>:5,4-<i>d</i>‘]dipyrimidine-4,5(3H,6H)-diones
  作者：Ming-Wu Ding、Sheng-Zhen Xu、Jun-Feng Zhao

  DOI：10.1021/jo048691v

  日期：2004.11.1

  The bis(carbodiimides) 4, obtained from bis-aza-Wittig reactions of bis(iminophosphorane) 3 with 2 equiv of aromatic isocyanates, were reacted with secondary amine to give symmetrically substituted 2,7-diaminothieno[2,3-d:5,4-d']dipyrimidine-4,5(3H,6H)-dione 6 in the presence of a catalytic amount of EtO-Na+ Reactions of 4 with phenols or ROH in the presence of a catalytic amount of potassium carbonate or RO-Na+ gave symmetrically substituted 2,7-diaryl(alkyl)oxythieno[2,3-d:5,4-d']dipyrimidine-4,5(3H,6H)-diones 6 in satisfactory yields. However, iminophosphoranes 9 were obtained via reaction of bis(iminophosphorane) 3 with 1 equiv of aromatic isocyanate and subsequent reaction with an amine in the presence of a catalytic amount of EtO-Na+. Further reaction of iminophosphoranes 9 with aromatic isocyanates and various nucleophile generated unsymmetrically substituted thieno[2,3-d:5,4-d']dipyrimidine-4,5(3H,6H)-diones 12 in good yields.