5-ethoxycarbonyl-4-(2-isothiocyanatophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one | 1248635-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-ethoxycarbonyl-4-(2-isothiocyanatophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one
• CAS: 1248635-38-2
• 化学式: C₁₅H₁₅N₃O₃S
• 分子量: 317.368
• InChiKey: KVOFGZBTZUVBDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  79.79
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-ethoxycarbonyl-4-(2-isothiocyanatophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以0.26 g的产率得到1-ethoxycarbonyl-2-methyl-6-thioxo-3,6,7,11b-tetrahydro-4H-pyrimido[1,6-c]quinazolin-4-one
  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：

  二硫化碳 、 5-ethoxycarbonyl-6-methyl-4-(2-(triphenylphosphoranylideneamino)phenyl)-3,4-dihydropyrimidin-2(1H)-one 以 乙腈 为溶剂， 反应 12.0h， 生成 5-ethoxycarbonyl-4-(2-isothiocyanatophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one
  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