N-(4-methoxyphenyl)-N-methyl-2-oxoacetamide | 1233940-52-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-methoxyphenyl)-N-methyl-2-oxoacetamide
• CAS: 1233940-52-7
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: SUOXSXPFLSVZLZ-UHFFFAOYSA-N

物化性质

• 沸点：
  323.0±44.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-methoxyphenyl)-N-methyl-2-oxoacetamide 在 palladium dichloride 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以93%的产率得到5-methoxy-1-methyl-1H-indole-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
• 作为产物：
  描述：

  C₁₀H₁₃NO₃ 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以90%的产率得到N-(4-methoxyphenyl)-N-methyl-2-oxoacetamide
  参考文献：
  名称：

  IBX促进的α-羟基酰胺的多米诺骨反应：一种简单的一锅合成的靛红†

  摘要：

  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。

  DOI：

  10.1039/c5ra25036f

文献信息

• 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。
• PhI(OAc)₂-promoted metal-free oxidation of 2-oxoaldehydes: a facile one-pot synthesis of cyanoformamides
  作者：Zhen Zhan、Xu Cheng、Yang Zheng、Xiaojun Ma、Xiaoyu Wang、Li Hai、Yong Wu

  DOI：10.1039/c5ra14409d

  日期：——

  A novel, efficient and environmental method for the conversion of 2-oxoaldehydes into cyanoformamides with iodosobenzene diacetate as oxidant has been developed.

  已开发出一种新颖、高效且环保的方法，可将2-氧代醛转化为氰基甲酰胺，其氧化剂为双乙酸碘苯。
• 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.