tert-butyl 5,6-dibenzoyl-2-phenylpyrimidine-1(6H)-carboxylate | 1527528-07-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl 5,6-dibenzoyl-2-phenylpyrimidine-1(6H)-carboxylate
• 英文别名: tert-butyl 4,5-dibenzoyl-2-phenyl-4H-pyrimidine-3-carboxylate
• CAS: 1527528-07-9
• 化学式: C₂₉H₂₆N₂O₄
• 分子量: 466.536
• InChiKey: IZNOZBQAJSYLTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-tert-butoxycarbonyl-4-dimethylamino-2-phenyl-1,3-diaza-1,3-butadiene 、 反-1,2-二苯酰乙烯 在 lithium carbonate 、 碘甲烷 作用下， 以 均三甲苯 、 二氯甲烷 为溶剂， 反应 19.0h， 以77%的产率得到tert-butyl 5,6-dibenzoyl-2-phenylpyrimidine-1(6H)-carboxylate
  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

文献信息

• 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
  作者：Yoshio Nishimura、Hidetsura Cho

  DOI：10.1016/j.tetlet.2013.11.038

  日期：2014.1

  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.