6-methylmercaptothiocarbonyl-5-(4-bromophenyl)-7-(4-methoxyphenyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine | 1255769-97-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 6-methylmercaptothiocarbonyl-5-(4-bromophenyl)-7-(4-methoxyphenyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine
• 英文别名: Methyl 5-(4-bromophenyl)-7-(4-methoxyphenyl)-1,3-dimethyl-2,4-dioxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carbodithioate
• CAS: 1255769-97-1
• 化学式: C₂₄H₂₂BrN₃O₃S₂
• 分子量: 544.493
• InChiKey: NACZNHDVHJJONV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,3-二甲基-6-氨基脲嘧啶 、 S-methyl 3-oxo-3-(4-methoxylphenyl)propanedithioate 、 对溴苯甲醛 在 H₂SO₄-SiO₂ 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以62%的产率得到6-methylmercaptothiocarbonyl-5-(4-bromophenyl)-7-(4-methoxyphenyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine
  参考文献：
  名称：

  Biginelli and Hantzsch-Type Reactions Leading to Highly Functionalized Dihydropyrimidinone, Thiocoumarin, and Pyridopyrimidinone Frameworks via Ring Annulation with β-Oxodithioesters

  摘要：

  An efficient and highly convergent route to dihydropyrimidinones (DHPMs) and hitherto unreported dihydropyridopyrimidinones has been developed by one-pot, three-component cyclocondensation of aromatic aldehydes, beta-oxodithioesters, and urea/6-amino-1,3-dimethyluracil in the presence of recyclable SiO2-H2SO4 On the other hand, salicylaldehyde, beta-oxodithioester, and urea reacted under similar conditions to afford the 3-aroyl/heteroaroyl-2H-chromen-2-thiones in high yields instead of Biginelli product The attractive feature of this approach is the synthesis of three important bioactive heterocyclic frameworks from the same beta-oxodithioester under the similar reaction conditions, making this new strategy highly useful in diversity-oriented synthesis (DOS)

  DOI：

  10.1021/jo101572c

文献信息

• Biginelli and Hantzsch-Type Reactions Leading to Highly Functionalized Dihydropyrimidinone, Thiocoumarin, and Pyridopyrimidinone Frameworks via Ring Annulation with β-Oxodithioesters
  作者：Ganesh Chandra Nandi、Subhasis Samai、Maya Shankar Singh

  DOI：10.1021/jo101572c

  日期：2010.11.19

  An efficient and highly convergent route to dihydropyrimidinones (DHPMs) and hitherto unreported dihydropyridopyrimidinones has been developed by one-pot, three-component cyclocondensation of aromatic aldehydes, beta-oxodithioesters, and urea/6-amino-1,3-dimethyluracil in the presence of recyclable SiO2-H2SO4 On the other hand, salicylaldehyde, beta-oxodithioester, and urea reacted under similar conditions to afford the 3-aroyl/heteroaroyl-2H-chromen-2-thiones in high yields instead of Biginelli product The attractive feature of this approach is the synthesis of three important bioactive heterocyclic frameworks from the same beta-oxodithioester under the similar reaction conditions, making this new strategy highly useful in diversity-oriented synthesis (DOS)