(Z)-tert-butyl 2-(2-(4-methylphenylsulfonamido)benzoyl)-3-o-tolylacrylate | 1256493-51-2

• 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: (Z)-tert-butyl 2-(2-(4-methylphenylsulfonamido)benzoyl)-3-o-tolylacrylate
• CAS: 1256493-51-2
• 化学式: C₂₈H₂₉NO₅S
• 分子量: 491.608
• InChiKey: UEADVVHXBDDKTK-MOHJPFBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.71
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  89.54
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (Z)-tert-butyl 2-(2-(4-methylphenylsulfonamido)benzoyl)-3-o-tolylacrylate 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 96.0h， 生成 tert-butyl 4-hydroxy-2-o-tolyl-1-tosyl-1,2-dihydroquinoline-3-carboxylate 、 tert-butyl 4-hydroxy-2-o-tolyl-1-tosyl-1,2-dihydroquinoline-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
• 作为产物：
  描述：

  tert-butyl 3-(2-(4-methylphenylsulfonamido)phenyl)-3-oxopropanoate 、 2-甲基苯甲醛 在 哌啶 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 以59%的产率得到(Z)-tert-butyl 2-(2-(4-methylphenylsulfonamido)benzoyl)-3-o-tolylacrylate
  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