Methyl 6-(2-methoxy-2-oxoethyl)-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 590378-40-8

• 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 6-(2-methoxy-2-oxoethyl)-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: methyl 6-(2-methoxy-2-oxoethyl)-2-oxo-4-phenyl-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 590378-40-8
• 化学式: C₁₅H₁₆N₂O₅
• 分子量: 304.302
• InChiKey: XOCIODJYHHOENM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-丙酮二羧酸二甲酯 、 苯甲醛 、 尿素 在 对甲苯磺酸 作用下， 反应 3.0h， 以39%的产率得到Methyl 6-(2-methoxy-2-oxoethyl)-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Biginelli-like reaction with dialkyl acetone-1,3-dicarboxylates: a remarkable case of steric control

  摘要：

  A Biginelli-type condensation is described using dialkyl acetone-1,3-dicarboxylates as active methylene compounds for the preparation of monastrol analogues. Unexpectedly, the reaction with salicylaidehyde formed two different products depending on the ester alkyl group. This product dichotomy was found to be caused by the steric effects exerted by the alcohol terminus of the ester group in the active methylene component. Previous controversial results as to the structure of the Biginelli product 3 are also discussed. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.136

文献信息

• Biginelli-like reaction with dialkyl acetone-1,3-dicarboxylates: a remarkable case of steric control
  作者：Jan Sve˘tlík、Lucia Veizerová、Viktor Kettmann

  DOI：10.1016/j.tetlet.2008.03.136

  日期：2008.5

  A Biginelli-type condensation is described using dialkyl acetone-1,3-dicarboxylates as active methylene compounds for the preparation of monastrol analogues. Unexpectedly, the reaction with salicylaidehyde formed two different products depending on the ester alkyl group. This product dichotomy was found to be caused by the steric effects exerted by the alcohol terminus of the ester group in the active methylene component. Previous controversial results as to the structure of the Biginelli product 3 are also discussed. (c) 2008 Elsevier Ltd. All rights reserved.