ethyl (4S,10aR)-2-methyl-5-oxo-4-(2-thienyl)-1,4,5,7,8,9,-10,10a-octahydropyrido[2',3':3,4]pyrrolo[1,2-a]pyrimidine-3-carboxylate | 1581710-38-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: ethyl (4S,10aR)-2-methyl-5-oxo-4-(2-thienyl)-1,4,5,7,8,9,-10,10a-octahydropyrido[2',3':3,4]pyrrolo[1,2-a]pyrimidine-3-carboxylate
• CAS: 1581710-38-4
• 化学式: C₁₈H₂₁N₃O₃S
• 分子量: 359.449
• InChiKey: PWDUKHPMPZLEJO-CZUORRHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  70.67
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1,3-丙二胺 、 diethyl (4R)-2-formyl-6-methyl-4-(thien-2'-yl)-1,4-dihydropyridine-3,5-dicarboxylate 在 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以61%的产率得到ethyl (4S,10aR)-2-methyl-5-oxo-4-(2-thienyl)-1,4,5,7,8,9,-10,10a-octahydropyrido[2',3':3,4]pyrrolo[1,2-a]pyrimidine-3-carboxylate
  参考文献：
  名称：

  Synthesis of novel chiral 1,4-dihydropyridinyl Schiff-base ligands, with characterization and evaluation of calcium channel blocker activity

  摘要：

  Treatment of 2-formyl-1,4-dihydropyridines with primary diamines gave rise to different products depending on the molar ratio of reactants. In the case of stoichiometric amounts of substrate and reactant, only tricyclic cis-diastereoisomer was obtained in yields ranging from 53 % up to 54 %. In addition, reaction of the above carboxaldehyde with primary diamines in a molar ratio of 2/1 resulted in the formation of bis-iminoderivatives in high yields of 80-97 %. All these compounds were examined as ligands for synthesis of complexes with metal salts. Ultimately, the selected compounds, in enantiopure and racemic form, were tested for their effect on both basal and agonist (or vanadate)-induced Ca-45(2+) influx.

  DOI：

  10.1007/s00706-014-1164-2
• 作为试剂：
  描述：

  diethylzinc 、 苯甲醛 在 ethyl (4S,10aR)-2-methyl-5-oxo-4-(2-thienyl)-1,4,5,7,8,9,-10,10a-octahydropyrido[2',3':3,4]pyrrolo[1,2-a]pyrimidine-3-carboxylate 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 24.25h， 生成 (R)-(+)-1-苯基-1-丙醇 、 S(-)-1-苯基-1-丙醇
  参考文献：
  名称：

  Synthesis of novel chiral 1,4-dihydropyridinyl Schiff-base ligands, with characterization and evaluation of calcium channel blocker activity

  摘要：

  Treatment of 2-formyl-1,4-dihydropyridines with primary diamines gave rise to different products depending on the molar ratio of reactants. In the case of stoichiometric amounts of substrate and reactant, only tricyclic cis-diastereoisomer was obtained in yields ranging from 53 % up to 54 %. In addition, reaction of the above carboxaldehyde with primary diamines in a molar ratio of 2/1 resulted in the formation of bis-iminoderivatives in high yields of 80-97 %. All these compounds were examined as ligands for synthesis of complexes with metal salts. Ultimately, the selected compounds, in enantiopure and racemic form, were tested for their effect on both basal and agonist (or vanadate)-induced Ca-45(2+) influx.

  DOI：

  10.1007/s00706-014-1164-2