1,3-dimethyl-3-(2-oxo-2-(thiophen-2-yl)ethyl)indolin-2-one | 1470365-13-9

• 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: 1,3-dimethyl-3-(2-oxo-2-(thiophen-2-yl)ethyl)indolin-2-one
• 英文别名: 1,3-Dimethyl-3-(2-oxo-2-thiophen-2-ylethyl)indol-2-one
• CAS: 1470365-13-9
• 化学式: C₁₆H₁₅NO₂S
• 分子量: 285.367
• InChiKey: UDBFIDNSGVKRPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 N-methyl-N-phenylmethacrylamide 在 叔丁基过氧化氢 、 iron(III) chloride 作用下， 以 癸烷 、 氯苯 为溶剂， 反应 1.0h， 以61%的产率得到1,3-dimethyl-3-(2-oxo-2-(thiophen-2-yl)ethyl)indolin-2-one
  参考文献：
  名称：

  Iron-catalyzed carbonylation–arylation of N-arylacrylamides for synthesis of oxindole derivatives

  摘要：

  An efficient method for oxindole synthesis is established by iron-catalyzed carbonylation-arylation of N-arylacrylamides with aldehydes. 3-Functionalized oxindoles are synthesized smoothly using FeCl3 as catalyst and TBHP as oxidant. The obtained oxindoles can be used for further transformations to give diverse indole alkaloid structure motifs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.048

文献信息

• Visible-Light-Mediated Photocatalytic Difunctionalization of Olefins by Radical Acylarylation and Tandem Acylation/Semipinacol Rearrangement
  作者：Giulia Bergonzini、Carlo Cassani、Haldor Lorimer-Olsson、Johanna Hörberg、Carl-Johan Wallentin

  DOI：10.1002/chem.201504985

  日期：2016.3.1

  A novel method for the mild photoredox‐mediated tandem radical acylarylation and tandem acylation/semipinacol rearrangement has been developed. The synthesis of highly functionalized ketones bearing all‐carbon α‐ or β‐quaternary centers has been achieved using easily available symmetric aromatic carboxylic anhydrides as the acyl radical source. The method allows for a straightforward introduction of

  开发了一种轻度的光氧化还原介导的串联自由基酰基化和串联酰化/ semipinacol重排的新方法。使用容易获得的对称芳族羧酸酐作为酰基自由基源，可以合成带有全碳α-或β-季中心的高度官能化的酮。该方法允许在单个操作中直接引入酮基官能团并伴随分子复杂性的构建。
• Acyl Radicals from Aromatic Carboxylic Acids by Means of Visible-Light Photoredox Catalysis
  作者：Giulia Bergonzini、Carlo Cassani、Carl-Johan Wallentin

  DOI：10.1002/anie.201506432

  日期：2015.11.16

  Simple and abundant carboxylic acids have been used as acyl radical precursor by means of visible‐light photoredox catalysis. By the transient generation of a reactive anhydride intermediate, this redox‐neutral approach offers a mild and rapid entry to high‐value heterocyclic compounds without the need of UV irradiation, high temperature, high CO pressure, tin reagents, or peroxides.

  通过可见光光氧化还原催化，简单而丰富的羧酸已被用作酰基自由基前体。通过瞬时生成反应性酸酐中间体，这种氧化还原中性方法可以温和快速地生成高价值杂环化合物，而无需紫外线照射、高温、高二氧化碳压力、锡试剂或过氧化物。
• Metal-Free Generation of Acyl Radical via Photoinduced Single-Electron Transfer from Lewis Base to Acyl Chloride
  作者：Lei Bao、Zhi-Xiang Wang、Xiang-Yu Chen

  DOI：10.1021/acs.orglett.2c03339

  日期：2022.11.11

  We herein describe a simple approach for generating acyl radical from acyl chloride via photoinduced single-electron transfer. It has been demonstrated that the generated acyl radicals could react with various substrates, including isocyanides, methacrylamides, alkenes, alkynes, and enynes, to afford diverse heterocycles (>10 classes). Mechanistic analyses show that a photoactive charge transfer complex

  我们在此描述了一种通过光诱导单电子转移从酰氯产生酰基自由基的简单方法。已经证明，产生的酰基自由基可以与各种底物反应，包括异氰化物、甲基丙烯酰胺、烯烃、炔烃和烯炔，以提供多种杂环（> 10 类）。机理分析表明，酰氯和路易斯碱添加剂之间的光活性电荷转移络合物参与了酰基自由基的光生成。该研究举例说明了一种新的简单的羰基化合物光活化方法。
• Silver-Catalyzed Decarboxylative Acylarylation of Acrylamides with α-Oxocarboxylic Acids in Aqueous Media
  作者：Hua Wang、Li-Na Guo、Xin-Hua Duan

  DOI：10.1002/adsc.201300468

  日期：2013.8.12

  AbstractA mild and efficient silver‐catalyzed acylarylation of activated alkenes with easily available α‐oxocarboxylic acids has been developed. The reactions provide a rapid access to a variety of functionalized oxindoles via a tandem decarboxylative radical cyclization strategy. This transformation proceeds well under mild reaction conditions and exhibits excellent functional group tolerance, affording the desired oxindoles in good to excellent yields.magnified image