(E)-5-chloro-3-hydroxy-3-(2-oxo-4-phenylbut-3-en-1-yl)indolin-2-one

• 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: (E)-5-chloro-3-hydroxy-3-(2-oxo-4-phenylbut-3-en-1-yl)indolin-2-one
• 英文别名: 5-chloro-3-hydroxy-3-[(3E)-2-oxo-4-phenylbut-3-en-1-yl]-1,3-dihydro-2H-indol-2-one；5-chloro-3-hydroxy-3-[(E)-2-oxo-4-phenylbut-3-enyl]-1H-indol-2-one
• 化学式: C₁₈H₁₄ClNO₃
• 分子量: 327.767
• InChiKey: DJKAQRZCSJVIRP-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5-chloro-3-hydroxy-3-(2-oxo-4-phenylbut-3-en-1-yl)indolin-2-one 在 碘 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以75%的产率得到(Z)-5-chloro-3-((E)-2-oxo-4-phenylbut-3-en-1-ylidene)indolin-2-one
  参考文献：
  名称：

  Aqueous NH₃-mediated syntheses of 2-styrylquinoline-4-carboxamides by domino ring opening cyclization strategy

  摘要：

  A straightforward and efficient protocol for the synthesis of medicinally relevant 2-styrylquinoline-4-carboxamide has been developed by aqueous ammonia-mediated domino ring-opening and cyclization strategy of 3-hydroxyoxindole. The starting precursors 3-hydroxyoxindoles were easily prepared through organocatalytic "on water" reaction of isatin and benzalacetone in high yields. The wide substrate scope with operationally simple experimental procedures provides an opportunity to create library of 2-styrylquinoline-4-carboxamide derivatives.

  DOI：

  10.1080/00397911.2020.1822409
• 作为产物：
  描述：

  5-氯靛红 、 苄叉丙酮 在 三乙烯二胺 作用下， 以 水 为溶剂， 反应 1.5h， 以72%的产率得到(E)-5-chloro-3-hydroxy-3-(2-oxo-4-phenylbut-3-en-1-yl)indolin-2-one
  参考文献：
  名称：

  Aqueous NH₃-mediated syntheses of 2-styrylquinoline-4-carboxamides by domino ring opening cyclization strategy

  摘要：

  A straightforward and efficient protocol for the synthesis of medicinally relevant 2-styrylquinoline-4-carboxamide has been developed by aqueous ammonia-mediated domino ring-opening and cyclization strategy of 3-hydroxyoxindole. The starting precursors 3-hydroxyoxindoles were easily prepared through organocatalytic "on water" reaction of isatin and benzalacetone in high yields. The wide substrate scope with operationally simple experimental procedures provides an opportunity to create library of 2-styrylquinoline-4-carboxamide derivatives.

  DOI：

  10.1080/00397911.2020.1822409