tert-butyl 2-(4-ethylphenyl)-1,2,3,4-tetrahydro-4-oxo-1-tosylquinoline-3-carboxylate | 1256493-59-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: tert-butyl 2-(4-ethylphenyl)-1,2,3,4-tetrahydro-4-oxo-1-tosylquinoline-3-carboxylate
• CAS: 1256493-59-0
• 化学式: C₂₉H₃₁NO₅S
• 分子量: 505.635
• InChiKey: MVPUFONFOKRZFU-FXDYGKIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  80.75
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(4-ethylphenyl)-1,2,3,4-tetrahydro-4-oxo-1-tosylquinoline-3-carboxylate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以91%的产率得到(S)-2-(4-ethylphenyl)-2,3-dihydro-1-tosylquinolin-4(1H)-one
  参考文献：
  名称：

  Asymmetric Synthesis of 2-Aryl-2,3-dihydro-4-quinolones via Bifunctional Thiourea-Mediated Intramolecular Cyclization

  摘要：

  A novel asymmetric preparation of optically enriched 2-aryl-2,3-dihydroquinolin-4(1H)-ones has been developed. By installing a sulfonyl group on the nitrogen of the anilines and an ester function on the unsaturated ketones, an intramolecular organocatalytic cyclization took place readily in a stereoselective manner, resulting in the formation of dihydroquinolones with high enantioselectivity.

  DOI：

  10.1021/ol102519z
• 作为产物：
  描述：

  (Z)-tert-butyl 3-(4-ethylphenyl)-2-(2-(4-methylphenylsulfonamido)benzoyl)acrylate 在 N-[3,5-双(三氟甲基)苯基]-N′-[(9R)-6′-甲氧基-9-金鸡宁]硫脲 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以98%的产率得到tert-butyl 2-(4-ethylphenyl)-1,2,3,4-tetrahydro-4-oxo-1-tosylquinoline-3-carboxylate
  参考文献：
  名称：

  Asymmetric Synthesis of 2-Aryl-2,3-dihydro-4-quinolones via Bifunctional Thiourea-Mediated Intramolecular Cyclization

  摘要：

  A novel asymmetric preparation of optically enriched 2-aryl-2,3-dihydroquinolin-4(1H)-ones has been developed. By installing a sulfonyl group on the nitrogen of the anilines and an ester function on the unsaturated ketones, an intramolecular organocatalytic cyclization took place readily in a stereoselective manner, resulting in the formation of dihydroquinolones with high enantioselectivity.

  DOI：

  10.1021/ol102519z