ethyl 4-(benzenesulfonylmethyl)-1,2,3,4-tetrahydro-6-methyl-2-oxopyrimidine-5-carboxylate

• 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: ethyl 4-(benzenesulfonylmethyl)-1,2,3,4-tetrahydro-6-methyl-2-oxopyrimidine-5-carboxylate
• 英文别名: ethyl 4-(benzenesulfonylmethyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₅H₁₈N₂O₅S
• 分子量: 338.384
• InChiKey: DSVBCHDLCWTJDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-甲基-2-氧代-1,2,3,4-四氢嘧啶-5-羧酸乙酯 在 正丁基锂 、 硝酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 ethyl 4-(benzenesulfonylmethyl)-1,2,3,4-tetrahydro-6-methyl-2-oxopyrimidine-5-carboxylate
  参考文献：
  名称：

  A highly regio- and chemoselective addition of carbon nucleophiles to pyrimidinones. A new route to C4 elaborated Biginelli compounds

  摘要：

  Ethyl 6-methyl-pyrimidine-2-one-5-carboxylates react with C-nucleophiles in a diversity oriented synthetic sequence to afford C4 substituted congeners of medicinally potent Biginelli dihydropyrimidinones, in a highly regioselective manner. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.111

文献信息

• An Efficacious Protocol for 4-Substituted 3,4-Dihydropyrimidinones: Synthesis and Calcium Channel Binding Studies
  作者：Kamaljit Singh、Divya Arora、Danielle Falkowski、Qingxin Liu、Robert S. Moreland

  DOI：10.1002/ejoc.200900208

  日期：2009.7

  anion of enantiopure chiral auxiliary (1R,2S,5R)-(-)-methyl (S)-p-toluenesulfinate to afford C-4 substituted and enantiopure congeners of medicinally potent Biginelli dihydropyrimidinones. The calcium channel blocking activity of some of the compounds was evaluated and compared with nifedipine for their ability to relax a membrane depolarization induced contraction.

  1,2-二氢-1,6-二甲基/ 6-甲基-2-氧嘧啶-5-羧酸乙酯与C-亲核试剂以及对映纯手性助剂（1R，2S，5R）-（-）-甲基的阴离子反应（S）-对甲苯磺酸盐，可得到具有药效的比吉内利二氢嘧啶酮的C-4取代对映体和对映体纯同系物。对某些化合物的钙通道阻断活性进行了评估，并与硝苯地平比较了它们舒张膜去极化引起的收缩的能力。
• A highly regio- and chemoselective addition of carbon nucleophiles to pyrimidinones. A new route to C4 elaborated Biginelli compounds
  作者：Kamaljit Singh、Divya Arora、Sukhdeep Singh

  DOI：10.1016/j.tetlet.2006.12.111

  日期：2007.2

  Ethyl 6-methyl-pyrimidine-2-one-5-carboxylates react with C-nucleophiles in a diversity oriented synthetic sequence to afford C4 substituted congeners of medicinally potent Biginelli dihydropyrimidinones, in a highly regioselective manner. (c) 2006 Elsevier Ltd. All rights reserved.