3-hydroxy-3-(2-oxopentyl)indolin-2-one | 1360439-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-hydroxy-3-(2-oxopentyl)indolin-2-one
• 英文别名: 3-hydroxy-3-(2-oxopentyl)-1H-indol-2-one
• CAS: 1360439-71-9
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: VNUZUXZVIDWFCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.4
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-oxocaproic acid 、 靛红 以 乙酸乙酯 为溶剂， 反应 4.0h， 以88%的产率得到3-hydroxy-3-(2-oxopentyl)indolin-2-one
  参考文献：
  名称：

  分子筛介导的β-酮酸脱羧曼尼希和羟醛反应

  摘要：

  报道了分子筛介导的β-酮酸与磺酰基亚胺的曼尼希脱羧反应。该方案可有效制备合成上有用的β-氨基酮。还描述了类似的分子筛促进的β-酮酸和靛红之间的脱羧醛醇缩合反应，其以优异的产率提供了生物活性的3-取代的-3-羟基-吲哚。

  DOI：

  10.1016/j.tetlet.2013.06.030

文献信息

• Mapping the Surface Groups of Amine-Rich Carbon Dots Enables Covalent Catalysis in Aqueous Media
  作者：Giacomo Filippini、Francesco Amato、Cristian Rosso、Giulio Ragazzon、Alberto Vega-Peñaloza、Xavier Companyó、Luca Dell’Amico、Marcella Bonchio、Maurizio Prato

  DOI：10.1016/j.chempr.2020.08.009

  日期：2020.11

  Carbon nanodots stand as the missing link between the molecular and the nanoscale world, owing to the unique molecular-like behavior emerging from their synthetic precursors. A converging set of analytical and spectroscopic data yields a precise inventory of the surface reactive groups of amine-rich carbon dots (NCDs-1). As a result, NCDs-1 provide a multi-functional nano-platform that is able to covalently activate carbonyl groups, form iminium-ions and enamine intermediates, and efficiently promote diverse aminocatalytic transformations in water. Remarkably, the catalytic activity of carbon dots can also govern the stereoselectivity in the bond-forming event. Indeed, the use of chiral carbon dots (NCDs-7) as catalysts affords the final aldol products with significant enantiomeric excess. The successful implementation of carbon nanostructures into chemical roles so far restricted to molecular systems opens new avenues for advanced applications where the nanoscale and the molecular realms will merge and complement each other.
• C<scp>U</scp>₂O-Catalyzed C(<scp>SP</scp>³)-H/C(<scp>SP</scp>³)-H Cross-Coupling Using TEMPO: Synthesis of 3-(2-Oxoalkyl)-3-hydroxyoxindoles
  作者：Baoshuang Wang、Jiayi Zhu、Yang Wei、Guotian Luo、Hongen Qu、Liang-Xian Liu

  DOI：10.1080/00397911.2015.1111383

  日期：2015.12.17

  A simple, convenient, and efficient oxidative cross-coupling reaction of oxindoles with ketones toward a variety of 3-(2-oxoalkyl)-3-hydroxyoxindoles in moderate to excellent yields has been developed. This transformation proceeds via a tandem oxidative cross-coupling by using 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) in air as an environmentally benign oxidant. This methodology provides an alternative approach for the direct generation of all-carbon quaternary centers at the C3 position of oxindoles.