5-[3-(4-bromophenyl)-2-propenoyl]-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one | 924724-65-2

• 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]-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: 5-[3-(4-bromophenyl)prop-2-enoyl]-6-methyl-4-phenyl-3,4-dihydro-1H-pyrimidin-2-one
• CAS: 924724-65-2
• 化学式: C₂₀H₁₇BrN₂O₂
• 分子量: 397.271
• InChiKey: NPWMPBIVIQNNBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  溴乙烷 、 5-[3-(4-bromophenyl)-2-propenoyl]-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one 在 potassium hydroxide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以32%的产率得到5-[3-(4-bromophenyl)-2-propenoyl]-1-ethyl-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 硫酸 、 sodium hydride 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 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]-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