5-methoxycarbonyl-6-methyl-4-phenyl-1,4-dihydropyrimidine | 126827-33-6

• 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: 5-methoxycarbonyl-6-methyl-4-phenyl-1,4-dihydropyrimidine
• 英文别名: Methyl 6-methyl-4-phenyl-1,4-dihydropyrimidine-5-carboxylate
• CAS: 126827-33-6
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: GXHPZZTYUPKOBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxycarbonyl-6-methyl-4-phenyl-1,4-dihydropyrimidine 、 氯甲酸乙酯 以 四氢呋喃 为溶剂， 生成 3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidine
  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
• 作为产物：
  描述：

  methyl 6-methyl-2-(methylthio)-4-phenyl-1,4-dihydropyrimidine-5-carboxylate 在 镍 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以69%的产率得到5-methoxycarbonyl-6-methyl-4-phenyl-1,4-dihydropyrimidine
  参考文献：
  名称：

  Alkylation and reductive dethionation of 2-thioxo- and 1,2,3,4-tetrahydropyrimidine-5-carboxylic acid derivatives

  摘要：

  DOI：

  10.1007/bf00479609

文献信息

• XANINA, E. L.;ZOLOTOYABKO, R. M.;MUTSENIETSE, D. X.;DUBUR, G. YA., XIMIYA GETEROTSIKL. SOED.,(1989) N, S. 1076-1082
  作者：XANINA, E. L.、ZOLOTOYABKO, R. M.、MUTSENIETSE, D. X.、DUBUR, G. YA.

  DOI：——

  日期：——
• Alkylation and reductive dethionation of 2-thioxo- and 1,2,3,4-tetrahydropyrimidine-5-carboxylic acid derivatives
  作者：E. L. Khanina、R. M. Zolotoyabko、D. Kh. Mutsenietse、G. Ya. Dubur

  DOI：10.1007/bf00479609

  日期：1989.8
• 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.