(E)-3-hydroxy-5-methyl-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)-3-hydroxy-5-methyl-3-(2-oxo-4-phenylbut-3-en-1-yl)indolin-2-one
• 英文别名: (E)-5-methyl-3-hydroxy-3-(2-oxo-4-phenylbut-3-en-1-yl)indolin-2-one；3-hydroxy-5-methyl-3-[(3E)-2-oxo-4-phenylbut-3-en-1-yl]-1,3-dihydro-2H-indol-2-one；3-hydroxy-5-methyl-3-[(E)-2-oxo-4-phenylbut-3-enyl]-1H-indol-2-one
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: XSNAUVBEJVFEBA-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 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)-3-hydroxy-5-methyl-3-(2-oxo-4-phenylbut-3-en-1-yl)indolin-2-one 在 氨 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 以60%的产率得到(E)-6-methyl-2-styrylquinoline-4-carboxamide
  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：

  苯甲醛 在 L-精氨酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 60.0h， 生成 (E)-3-hydroxy-5-methyl-3-(2-oxo-4-phenylbut-3-en-1-yl)indolin-2-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel C3-functionalized oxindoles as potential Pim-1 kinase inhibitors

  摘要：

  一系列新型的C3-功能化氧吲哚，3-(2-氧代-4-苯基丁-3-烯-1-基亚甲基)吲哚啉-2-酮作为潜在的Pim-1激酶抑制剂被设计、合成并用于研究抑制人类癌细胞增殖。

  DOI：

  10.1039/c5ra00177c

文献信息

• Facile Creation of 3-Substituted-3-Hydroxy-2-Oxindoles by Arginine-Catalyzed Aldol Reactions of α,β-Unsaturated Ketones with Isatins
  作者：Tingting Yan、Xiaoyan Wang、Hongbao Sun、Jie Liu、Yongmei Xie

  DOI：10.3390/molecules181214505

  日期：——

  An efficient approach for the synthesis of 3-substituted-3-hydroxy-2-oxindoles has been achieved via an aldol reaction of α,β-unsaturated ketones and isatins using arginine as an organocatalyst. A range of 3-substituted-3-hydroxy-2-oxindoles were obtained in moderate to high (up to 99%) yields. These 3-substituted-3-hydroxy-2-oxindoles with an additional enone moiety provide an opportunity for further elaboration of the products and for potentially interesting biological activities. In addition, the formation of 3-substituted-3-hydroxy-2-oxindole 3a was confirmed by X-ray crystallography. The possible reaction mechanism reveals that the reaction proceeds via a double action process.

  使用精氨酸作为有机催化剂，通过 α,β-不饱和酮和靛红的醇醛缩合反应，实现了合成 3-取代-3-羟基-2-羟吲哚的有效方法。以中等到高（高达 99%）的产率获得了一系列 3-取代-3-羟基-2-羟吲哚。这些带有额外烯酮部分的 3-取代-3-羟基-2-羟吲哚为进一步精制产品和潜在有趣的生物活性提供了机会。此外，X射线晶体学证实了3-取代-3-羟基-2-羟吲哚3a的形成。可能的反应机理表明该反应通过双作用过程进行。
• Design, synthesis and biological evaluation of novel C3-functionalized oxindoles as potential Pim-1 kinase inhibitors
  作者：Hong-bao Sun、Xiao-yan Wang、Guo-bo Li、Li-dan Zhang、Jie Liu、Li-feng Zhao

  DOI：10.1039/c5ra00177c

  日期：——

  A novel series of C3-functionalized oxindoles, 3-(2-oxo-4-phenylbut-3-en-1-ylidene) indolin-2-ones as potential Pim-1 kinase inhibitors, were designed, synthesized and investigated for inhibition of human cancer-cell proliferation.

  一系列新型的C3-功能化氧吲哚，3-(2-氧代-4-苯基丁-3-烯-1-基亚甲基)吲哚啉-2-酮作为潜在的Pim-1激酶抑制剂被设计、合成并用于研究抑制人类癌细胞增殖。
• Aqueous NH₃-mediated syntheses of 2-styrylquinoline-4-carboxamides by domino ring opening cyclization strategy
  作者：Chandran R.、Ashwini Pise、Suraj Kumar Shah、Rahul D.、Anirudh Baluni、Keshri Nath Tiwari

  DOI：10.1080/00397911.2020.1822409

  日期：2021.1.17

  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.