1-benzyl 5,6-diethyl 2-phenylpyrimidine-1,5,6(6H)-tricarboxylate | 1527528-05-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-benzyl 5,6-diethyl 2-phenylpyrimidine-1,5,6(6H)-tricarboxylate
• 英文别名: 3-O-benzyl 4-O,5-O-diethyl 2-phenyl-4H-pyrimidine-3,4,5-tricarboxylate
• CAS: 1527528-05-7
• 化学式: C₂₄H₂₄N₂O₆
• 分子量: 436.464
• InChiKey: WOXNMCLZQOVTIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  94.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-benzyloxycarbonyl-4-dimethylamino-2-phenyl-1,3-diaza-1,3-butadiene 、 马来酸二乙酯 在 lithium carbonate 、 碘甲烷 作用下， 以 二氯甲烷 为溶剂， 反应 64.0h， 以50%的产率得到1-benzyl 5,6-diethyl 2-phenylpyrimidine-1,5,6(6H)-tricarboxylate
  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.