1-(3-hydroxypropyl)-4-(4-bromophenyl)-5-carboethoxy-6-methyl-3,4-dihydropyrimidinone

• 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: 1-(3-hydroxypropyl)-4-(4-bromophenyl)-5-carboethoxy-6-methyl-3,4-dihydropyrimidinone
• 英文别名: Ethyl 6-(4-bromophenyl)-3-(3-hydroxypropyl)-4-methyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate
• 化学式: C₁₇H₂₁BrN₂O₄
• 分子量: 397.269
• InChiKey: UGVCPOCOZYJKTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(3-triisopropylsiloxypropyl)-4-(4-bromophenyl)-5-carboethoxy-6-methyl-3,4-dihydropyrimidinone 在 甲氧基三甲基硅烷 、 氢氟酸 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 3.5h， 生成 1-(3-hydroxypropyl)-4-(4-bromophenyl)-5-carboethoxy-6-methyl-3,4-dihydropyrimidinone
  参考文献：
  名称：

  Demonstration of the Feasibility of a Direct Solid-Phase Split-Pool Biginelli Synthesis of 3,4-Dihydropyrimidinones

  摘要：

  A direct, Lewis acid-catalyzed Bigineilli synthesis of 3,4-dihydropyrimidinones has been performed on high-capacity polystyrene macrobeads with a polymer O-silyi-attached N-(3-hydroxypropyl)urea. Resin-urea was first reacted separately with either 4-bromo- or 4-chlorobenzaldehyde and LiOTf in MeCN at 80 degreesC. After washing, the beads were pooled and reacted with ethyl acetoacetate and LiOTf in MeCN at 80 degreesC. Formation of only one kind of Biginelli product per bead demonstrated the feasibility of a solid-phase non-Atwal two-step split-and-pool synthesis of 3,4-dlhydropyrimidinones.

  DOI：

  10.1021/ol048946r

文献信息

• Demonstration of the Feasibility of a Direct Solid-Phase Split-Pool Biginelli Synthesis of 3,4-Dihydropyrimidinones
  作者：Michael J. Lusch、John A. Tallarico

  DOI：10.1021/ol048946r

  日期：2004.9.1

  A direct, Lewis acid-catalyzed Bigineilli synthesis of 3,4-dihydropyrimidinones has been performed on high-capacity polystyrene macrobeads with a polymer O-silyi-attached N-(3-hydroxypropyl)urea. Resin-urea was first reacted separately with either 4-bromo- or 4-chlorobenzaldehyde and LiOTf in MeCN at 80 degreesC. After washing, the beads were pooled and reacted with ethyl acetoacetate and LiOTf in MeCN at 80 degreesC. Formation of only one kind of Biginelli product per bead demonstrated the feasibility of a solid-phase non-Atwal two-step split-and-pool synthesis of 3,4-dlhydropyrimidinones.