1-tert-butyl 5-ethyl 6-benzoyl-2-phenylpyrimidine-1,5(6H)-dicarboxylate | 1527528-10-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-tert-butyl 5-ethyl 6-benzoyl-2-phenylpyrimidine-1,5(6H)-dicarboxylate
• CAS: 1527528-10-4
• 化学式: C₂₅H₂₆N₂O₅
• 分子量: 434.492
• InChiKey: BJVCQMLONFJRJV-UHFFFAOYSA-N

物化性质

• 沸点：
  546.3±60.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  85.27
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  反-3-苯甲酰丙烯酸乙酯 、 1-tert-butoxycarbonyl-4-dimethylamino-2-phenyl-1,3-diaza-1,3-butadiene 在 lithium carbonate 、 碘甲烷 作用下， 以 均三甲苯 、 二氯甲烷 为溶剂， 反应 52.0h， 以62%的产率得到tert-butyl 6-ethyl 5-benzoyl-2-phenylpyrimidine-1,6(6H)-dicarboxylate
  参考文献：
  名称：

  Synthesis of 4-unsubstituted dihydropyrimidines having acyl and alkoxycarbonyl groups at 5- and 6-positions by cyclization–elimination reactions using 1,3-diaza-1,3-butadienes

  摘要：

  A synthetic method for novel 4-unsubstituted 2-phenyldihydropyrimidines having acyl and alkoxycarbonyl groups at the 5- and 6-positions was developed. The cyclization of 4-dimethylamino-1,3-diaza-1,3-butadiene having N-protecting groups (Boc, Cbz) with 1,2-disubstituted ethylenes, such as diethyl maleate, diethyl fumarate, (Z)-hex-3-ene-2,5-dione, (E)-1,4-diphenylbut-2-ene-1,4-dione, and unsymmetrical (E)-ethyl 4-oxo-4-phenylbut-2-enoate, following the elimination of a dimethylamino group proceeded smoothly, producing the corresponding dihydropyrimidines in good overall yield. The N-protecting group (Boc) could be easily removed to obtain N-unsubstituted dihydropyrimidines as a mixture of tautomers, and their tautomeric behavior was analyzed by H-1 NMR spectroscopy. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.11.038