(Z)-tert-butyl 2-(2-(4-methylphenylsulfonamido)benzoyl)-3-phenylacrylate | 1256493-41-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (Z)-tert-butyl 2-(2-(4-methylphenylsulfonamido)benzoyl)-3-phenylacrylate
• 英文别名: tert-butyl (Z)-2-[2-[(4-methylphenyl)sulfonylamino]benzoyl]-3-phenylprop-2-enoate
• CAS: 1256493-41-0
• 化学式: C₂₇H₂₇NO₅S
• 分子量: 477.581
• InChiKey: PYHTXQLZQJBTLM-NKFKGCMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-tert-butyl 2-(2-(4-methylphenylsulfonamido)benzoyl)-3-phenylacrylate 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 28.0h， 以92%的产率得到(R)-tert-butyl 4-hydroxy-2-phenyl-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 、 苯甲醛 在 哌啶 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以68%的产率得到(Z)-tert-butyl 2-(2-(4-methylphenylsulfonamido)benzoyl)-3-phenylacrylate
  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.