3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-(thiophen-2-yl)-4-phenyl-1,2,3,4-tetrahydropyrimidine | 1254304-19-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-(thiophen-2-yl)-4-phenyl-1,2,3,4-tetrahydropyrimidine
• 英文别名: 3-O-ethyl 5-O-methyl 6-methyl-4-phenyl-2-thiophen-2-yl-2,4-dihydro-1H-pyrimidine-3,5-dicarboxylate
• CAS: 1254304-19-2
• 化学式: C₂₀H₂₂N₂O₄S
• 分子量: 386.472
• InChiKey: HQJHFKJCAWWBSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  96.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  噻吩 、 5-methoxycarbonyl-6-methyl-4-phenyl-1,4-dihydropyrimidine 、 氯甲酸乙酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以68%的产率得到3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-(thiophen-2-yl)-4-phenyl-1,2,3,4-tetrahydropyrimidine
  参考文献：
  名称：

  Regioselective addition reactions at C-2 of 3,4-dihydropyrimidinones. Synthesis and evaluation of multifunctionalized tetrahydropyrimidines

  摘要：

  Multifunctionalized tetrahydropyrimidines derivatives have been synthesized from Biginelli 3,4-dihydropyrimidin-2-(1H)-thiones (DHPMs) efficiently. The transformation includes desulfurization of DHPMs with Raney-Ni and subsequent regioselective C-2 functionalization using a variety of C-nucleophiles with simultaneous activation with ethyl chloroformate. Functionalized pyrimidine derivatives containing bulky substituents at C-2 of the pyrimidine ring are cytostatic. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.034

文献信息

• Regioselective addition reactions at C-2 of 3,4-dihydropyrimidinones. Synthesis and evaluation of multifunctionalized tetrahydropyrimidines
  作者：Kamaljit Singh、Divya Arora、Jan Balzarini

  DOI：10.1016/j.tet.2010.08.034

  日期：2010.10

  Multifunctionalized tetrahydropyrimidines derivatives have been synthesized from Biginelli 3,4-dihydropyrimidin-2-(1H)-thiones (DHPMs) efficiently. The transformation includes desulfurization of DHPMs with Raney-Ni and subsequent regioselective C-2 functionalization using a variety of C-nucleophiles with simultaneous activation with ethyl chloroformate. Functionalized pyrimidine derivatives containing bulky substituents at C-2 of the pyrimidine ring are cytostatic. (C) 2010 Elsevier Ltd. All rights reserved.