1-methyl-5-(thiophen-2-yl)indoline-2,3-dione | 1233940-41-4

• 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-methyl-5-(thiophen-2-yl)indoline-2,3-dione
• 英文别名: 1-Methyl-5-thiophen-2-ylindole-2,3-dione
• CAS: 1233940-41-4
• 化学式: C₁₃H₉NO₂S
• 分子量: 243.286
• InChiKey: AXJZJELQIIUJQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  在 palladium dichloride 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以76%的产率得到1-methyl-5-(thiophen-2-yl)indoline-2,3-dione
  参考文献：
  名称：

  Synthesis of isatins by the palladium-catalyzed intramolecular acylation of unactivated aryl C(sp²)–H bonds

  摘要：

  通过PdCl2催化的分子内酰化，从甲酰-N-芳酰胺合成吲哚酮。

  DOI：

  10.1039/c5ra23837d

文献信息

• IBX-promoted domino reaction of α-hydroxy amides: a facile one-pot synthesis of isatins
  作者：Yaoling Wang、Xu Cheng、Zhen Zhan、Xiaojun Ma、Ruifang Nie、Li Hai、Yong Wu

  DOI：10.1039/c5ra25036f

  日期：——

  A novel and temperature-controlled oxidation of α-hydroxy amides in the presence of IBX is described. The divergent one-pot synthesis of isatins and α-formyl amides was achieved in good to excellent yields under metal-free conditions. And these two mild methods can tolerate a variety of functional groups, and are operationally simple.

  描述了在IBX存在下α-羟基酰胺的新颖且温度控制的氧化。在无金属条件下，一锅法合成靛红和α-甲酰酰胺的收率很高。这两种温和的方法可以耐受多种功能基团，并且操作简单。
• Ru(III)-mediated intramolecular ortho-C(sp2)–H activation/oxidative acylation: one-pot synthesis of isatins from α-hydroxy amides
  作者：Yaoling Wang、Weijian Li、Xu Cheng、Zhen Zhan、Xiaojun Ma、Li Guo、Hui Jin、Yong Wu

  DOI：10.1016/j.tet.2016.04.041

  日期：2016.6

  A novel and efficient synthesis of isatins from α-hydroxy amides via ruthenium-mediated aromatic C–H activation is described. The reactions proceeded smoothly under mild conditions and generated the corresponding products in good to excellent yields. This methodology has a broad substrate scope and opens up an interesting and attractive avenue for the application of intramolecular ortho-C–H activation

  描述了通过钌介导的芳香族C–H活化从α-羟基酰胺合成一种新型高效的isatin 。反应在温和条件下平稳进行，并以良好至优异的产率产生相应的产物。该方法具有广泛的底物范围，并为分子内邻-C–H活化的应用开辟了有趣且有吸引力的途径。
• First Report on the Synthesis of Isatins via Pyridinium Chlorochromate Catalyzed Intramolecular Cyclization Reactions
  作者：Hongmei Yin、Yong Wu、Qiming Yue、Yaoling Wang、Li Hai、Li Guo

  DOI：10.1055/s-0035-1561372

  日期：——

  A new and useful strategy to synthesize isatins from α-formyl amides has been developed via one-pot intramolecular cyclization–oxidation reaction with the present of pyridinium chlorochromate (PCC). The reaction proceeded smoothly under air and has good yields of the corresponding products. Also, this methodology has a broad substrate scope, and is operationally simple and atom economic.

  通过在氯铬酸吡啶鎓 (PCC) 存在下的一锅分子内环化-氧化反应，开发了一种从 α-甲酰基酰胺合成靛红的新的有用策略。反应在空气中平稳进行，相应产物收率良好。此外，该方法具有广泛的底物范围，并且操作简单且原子经济。
• Ferric(III) chloride catalyzed intramolecular cyclization of N -alkyl-2-oxo-acetanilides: a facile access to isatins
  作者：Yang Zheng、Jue Li、Xinling Yu、Songyang Lv、Li Hai、Yong Wu

  DOI：10.1016/j.tetlet.2015.11.054

  日期：2016.1

  A facile strategy for the synthesis of isatins in high yield from N-alkyl-2-oxo-acetanilides has been developed via Friedel Crafts alkylation using FeCl3 as catalyst under air. This reaction proceeds through direct intramolecular addition and oxidation in one pot. Also this methodology is operationally simple, atom economical, and environment friendly. (C) 2015 Elsevier Ltd. All rights reserved.
• Copper-Catalyzed Intramolecular C−H Oxidation/Acylation of Formyl-<i>N</i>-arylformamides Leading to Indoline-2,3-diones
  作者：Bo-Xiao Tang、Ren-Jie Song、Cui-Yan Wu、Yu Liu、Ming-Bo Zhou、Wen-Ting Wei、Guo-Bo Deng、Du-Lin Yin、Jin-Heng Li

  DOI：10.1021/ja103426d

  日期：2010.7.7

  A new, efficient Cu-catalyzed intramolecular C-H oxidation/acylation method has been developed for the synthesis of substituted indoline-2,3-diones (isatins). In the presence of CuCl, and O-2, a variety of formyl-N-arylformamides underwent the tandem reaction to afford the corresponding indoline-2,3-diones in moderate to good yields. It is noteworthy that the reaction serves as the first example of transition-metal-catalyzed transformation for the preparation of indoline-2,3-diones.