dimethyl 5-iodo-4,6-diphenyl-1-tosyl-1,6-dihydropyridine-2,3-dicarboxylate | 1428550-23-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: dimethyl 5-iodo-4,6-diphenyl-1-tosyl-1,6-dihydropyridine-2,3-dicarboxylate
• 英文别名: dimethyl 3-iodo-1-(4-methylphenyl)sulfonyl-2,4-diphenyl-2H-pyridine-5,6-dicarboxylate
• CAS: 1428550-23-5
• 化学式: C₂₈H₂₄INO₆S
• 分子量: 629.472
• InChiKey: HZCCBZLFSITUNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 5-iodo-4,6-diphenyl-1-tosyl-1,6-dihydropyridine-2,3-dicarboxylate 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以62%的产率得到dimethyl 4,6-diphenyl-5-(phenylethynyl)-1-tosyl-1,6-dihydropyridine-2,3-dicarboxylate
  参考文献：
  名称：

  Cyclization and N-Iodosuccinimide-Induced Electrophilic Iodocyclization of 3-Aza-1,5-enynes To Synthesize 1,2-Dihydropyridines and 3-Iodo-1,2-dihydropyridines

  摘要：

  Metal-free cyclization and N-iodosuccinimide-induced electrophilic iodocyclization of readily available 3-aza-1,5-enynes have been developed. The reactions selectively give 1,2-dihydropyridines and 3-iodo-1,2-dihydropyridines involving an aza-Claisen rearrangement and a 6p-electrocyclization step. Furthermore, the reaction could be carried out in 10 g scale for the synthesis of 1,2-dihydropyridines.

  DOI：

  10.1021/jo400387b
• 作为产物：
  描述：

  dimethyl 2-(N-(1,3-diphenylprop-2-ynyl)-4-methylphenylsulfonamido)maleate 在 N-碘代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以93%的产率得到dimethyl 5-iodo-4,6-diphenyl-1-tosyl-1,6-dihydropyridine-2,3-dicarboxylate
  参考文献：
  名称：

  Cyclization and N-Iodosuccinimide-Induced Electrophilic Iodocyclization of 3-Aza-1,5-enynes To Synthesize 1,2-Dihydropyridines and 3-Iodo-1,2-dihydropyridines

  摘要：

  Metal-free cyclization and N-iodosuccinimide-induced electrophilic iodocyclization of readily available 3-aza-1,5-enynes have been developed. The reactions selectively give 1,2-dihydropyridines and 3-iodo-1,2-dihydropyridines involving an aza-Claisen rearrangement and a 6p-electrocyclization step. Furthermore, the reaction could be carried out in 10 g scale for the synthesis of 1,2-dihydropyridines.

  DOI：

  10.1021/jo400387b