methyl 4-(3-bromophenyl)-6-methyl-2-(2-thiophenyl)-1,4-dihydropyrimidine-5-carboxylate | 1375148-02-9

• 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: methyl 4-(3-bromophenyl)-6-methyl-2-(2-thiophenyl)-1,4-dihydropyrimidine-5-carboxylate
• 英文别名: Methyl 4-(3-bromophenyl)-6-methyl-2-thiophen-2-yl-1,4-dihydropyrimidine-5-carboxylate；methyl 4-(3-bromophenyl)-6-methyl-2-thiophen-2-yl-1,4-dihydropyrimidine-5-carboxylate
• CAS: 1375148-02-9
• 化学式: C₁₇H₁₅BrN₂O₂S
• 分子量: 391.288
• InChiKey: AWLVXNIYYHRGSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  78.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(3-bromophenyl)-6-methyl-2-(2-thiophenyl)-1,4-dihydropyrimidine-5-carboxylate 、 三丁基苯基锡 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以86%的产率得到methyl 4-(biphenyl-3-yl)-6-methyl-2-(2-thiophenyl)-1,4-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Optimized Liebeskind–Srogl coupling reaction between dihydropyrimidines and tributyltin compounds

  摘要：

  We developed an optimized Liebeskind-Srogl reaction in order to synthesize potentially biologically active 2-aryl-1,4-dihydropyrimidines. The pallado-catalyzed cross-coupling reaction between dihydropyrimidines and tributyltin derivatives appears particularly efficient (67-95% yields) when using CuBr.Me2S as the copper cofactor. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.067
• 作为产物：
  描述：

  2-三丁基甲锡烷基噻吩 、 5-(methoxycarbonyl)-6-methyl-4-(3-bromophenyl)-3,4-dihydropyrimidin-2(1H)-thione 在 四(三苯基膦)钯 、 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以91%的产率得到methyl 4-(3-bromophenyl)-6-methyl-2-(2-thiophenyl)-1,4-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Optimized Liebeskind–Srogl coupling reaction between dihydropyrimidines and tributyltin compounds

  摘要：

  We developed an optimized Liebeskind-Srogl reaction in order to synthesize potentially biologically active 2-aryl-1,4-dihydropyrimidines. The pallado-catalyzed cross-coupling reaction between dihydropyrimidines and tributyltin derivatives appears particularly efficient (67-95% yields) when using CuBr.Me2S as the copper cofactor. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.067