5-ethoxycarbonyl-6-methyl-1-phenyl-4-(2-(triphenylphosphoranylideneamino)phenyl)-3,4-dihydropyrimidine-2(1H)-thione | 1248635-32-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-ethoxycarbonyl-6-methyl-1-phenyl-4-(2-(triphenylphosphoranylideneamino)phenyl)-3,4-dihydropyrimidine-2(1H)-thione
• CAS: 1248635-32-6
• 化学式: C₃₈H₃₄N₃O₂PS
• 分子量: 627.747
• InChiKey: QUGFHZYXTXMXKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.77
• 重原子数：
  45.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  53.93
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-ethoxycarbonyl-6-methyl-1-phenyl-4-(2-(triphenylphosphoranylideneamino)phenyl)-3,4-dihydropyrimidine-2(1H)-thione 、 邻氯苯甲酰氯 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以92%的产率得到6-(2-chlorophenyl)-1-ethoxycarbonyl-2-methyl-3-phenyl-3,11b-dihydro-4H-pyrimido[1,6-c]quinazoline-4-thione
  参考文献：
  名称：

  New efficient synthesis of pyrimido[1,6-c]quinazolin-4-ones by a Biginelli 3CC/Staudinger/aza-Wittig sequence

  摘要：

  Dihydropyrimidinone azides 1, obtained from trimethylsilyl chloride-catalyzed Biginelli reaction of 2-azidobenzaldehyde, ethyl acetoacetate, and urea (or thiourea) at room temperature, reacted with triphenylphosphine to give iminophosphorane 2. A tandem aza-Wittig reaction of iminophosphorane 2 with isocyanate, acyl chloride or CS2 in the presence of K2CO3 or NEt3 generated pyrimido[1,6-c]quinazolin-4-ones 4, 6 or 8 in moderate to good yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.046
• 作为产物：
  描述：

  4-(2-azidophenyl)-5-ethoxycarbonyl-6-methyl-1-phenyl-3,4-dihydropyrimidine-2(1H)-thione 、 三苯基膦 以 二氯甲烷 为溶剂， 反应 2.0h， 以93%的产率得到5-ethoxycarbonyl-6-methyl-1-phenyl-4-(2-(triphenylphosphoranylideneamino)phenyl)-3,4-dihydropyrimidine-2(1H)-thione
  参考文献：
  名称：

  New efficient synthesis of pyrimido[1,6-c]quinazolin-4-ones by a Biginelli 3CC/Staudinger/aza-Wittig sequence

  摘要：

  Dihydropyrimidinone azides 1, obtained from trimethylsilyl chloride-catalyzed Biginelli reaction of 2-azidobenzaldehyde, ethyl acetoacetate, and urea (or thiourea) at room temperature, reacted with triphenylphosphine to give iminophosphorane 2. A tandem aza-Wittig reaction of iminophosphorane 2 with isocyanate, acyl chloride or CS2 in the presence of K2CO3 or NEt3 generated pyrimido[1,6-c]quinazolin-4-ones 4, 6 or 8 in moderate to good yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.046