(S)-2-(4-ethylphenyl)-2,3-dihydro-1-tosylquinolin-4(1H)-one | 1256493-68-1

• 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: (S)-2-(4-ethylphenyl)-2,3-dihydro-1-tosylquinolin-4(1H)-one
• 英文别名: (2S)-2-(4-ethylphenyl)-1-(4-methylphenyl)sulfonyl-2,3-dihydroquinolin-4-one
• CAS: 1256493-68-1
• 化学式: C₂₄H₂₃NO₃S
• 分子量: 405.518
• InChiKey: BPPAWUNLQWNUAA-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  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

文献信息

• Asymmetric Synthesis of 2-Aryl-2,3-dihydro-4-quinolones via Bifunctional Thiourea-Mediated Intramolecular Cyclization
  作者：Xiaoqian Liu、Yixin Lu

  DOI：10.1021/ol102519z

  日期：2010.12.3

  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.