5-[3-(4-bromophenyl)-2-propenoyl]-1-methoxymethyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one | 1612860-37-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 5-[3-(4-bromophenyl)-2-propenoyl]-1-methoxymethyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one
• CAS: 1612860-37-3
• 化学式: C₂₂H₂₁BrN₂O₃
• 分子量: 441.324
• InChiKey: RSYVSOWKNRFEBD-UHFFFAOYSA-N

物化性质

• 熔点：
  159-161 °C
• 沸点：
  622.4±55.0 °C(predicted)
• 密度：
  1.363±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.64
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-[3-(4-bromophenyl)-2-propenoyl]-1-methoxymethyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 以89%的产率得到5-[3-(4-bromophenyl)-2-propenoyl]-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  Synthesis of 5-Cinnamoyl-3,4-dihydropyrimidine-2(1H)-ones

  摘要：

  Two different approaches to the synthesis of 1-unsubstituted 5-cinnamoyl-3,4- dihydropyrimidine-2(1H)-ones have been developed. The first includes N(1)-protection of the starting 5-acetyl-3,4-dihydropyrimidine-2(1H)-one, further Claisen-Schmidt reaction, and cleavage of the protecting group. The second approach consists of one-pot condensation of urea, aldehyde, and cinnamoylacetone as dicarbonyl component. The 5-cinnamoylderivative synthesis starting from 5-acetyl-1,3-dialkyl-3,4-dihydropyrimidine2(1H)-ones is also shown.

  DOI：

  10.1080/00397911.2013.869341
• 作为产物：
  描述：

  5-乙酰基-6-甲基-4-苯基-3,4-二氢-1H-嘧啶-2-酮 在 sodium hydride 、 potassium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 6.0h， 生成 5-[3-(4-bromophenyl)-2-propenoyl]-1-methoxymethyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  Synthesis of 5-Cinnamoyl-3,4-dihydropyrimidine-2(1H)-ones

  摘要：

  Two different approaches to the synthesis of 1-unsubstituted 5-cinnamoyl-3,4- dihydropyrimidine-2(1H)-ones have been developed. The first includes N(1)-protection of the starting 5-acetyl-3,4-dihydropyrimidine-2(1H)-one, further Claisen-Schmidt reaction, and cleavage of the protecting group. The second approach consists of one-pot condensation of urea, aldehyde, and cinnamoylacetone as dicarbonyl component. The 5-cinnamoylderivative synthesis starting from 5-acetyl-1,3-dialkyl-3,4-dihydropyrimidine2(1H)-ones is also shown.

  DOI：

  10.1080/00397911.2013.869341