methyl 2-(acetyl)-3-(indol-3-yl)-3-(2-nitrophenyl)propanoate | 1381987-70-7

• 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: methyl 2-(acetyl)-3-(indol-3-yl)-3-(2-nitrophenyl)propanoate
• 英文别名: methyl 2-[1H-indol-3-yl-(2-nitrophenyl)methyl]-3-oxobutanoate
• CAS: 1381987-70-7
• 化学式: C₂₀H₁₈N₂O₅
• 分子量: 366.373
• InChiKey: GMDGQRQUHIKKLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吲哚 、 乙酰乙酸甲酯 、 邻硝基苯甲醛 在 Fe₃O₄(at)C-PW (12-Tungstophosphoric acid immobilized on carbon-coated Fe₃O₄ nanoparticles) 作用下， 以 水 为溶剂， 反应 0.5h， 以94%的产率得到methyl 2-(acetyl)-3-(indol-3-yl)-3-(2-nitrophenyl)propanoate
  参考文献：
  名称：

  Starch as a green source for Fe3O4@carbon core–shell nanoparticles synthesis: a support for 12-tungstophosphoric acid, synthesis, characterization, and application as an efficient catalyst

  摘要：

  12-磷钨酸（PW）负载在碳涂层Fe3O4纳米颗粒（Fe3O4@C-PW）上的制备通过水热和化学共沉淀的结合进行。由淀粉制成的中间碳层作为绿色材料，保护了磁性核心，并改善了纳米颗粒的分散性和催化活性。通过高分辨率透射电子显微镜（HRTEM）、傅里叶变换红外光谱（FT-IR）、振动样品磁力仪对该催化剂进行了表征，酸性特性则通过氨-程序升温脱附和电位滴定进行了研究。HRTEM图像显示，催化剂具有明确的核-壳结构，平均粒径为50纳米。FT-IR的表征数据表明，在合成Fe3O4@C-PW后，Keggin阴离子的基本结构和几何形状得以保留。合成的Fe3O4@C-PW作为纳米催化剂用于水中合成各种双（吲哚基）甲烷和β-功能化吲哚。该催化剂可以通过外部磁场简单回收，并可多次重复使用，而催化活性几乎没有显著损失。

  DOI：

  10.1007/s11164-015-2229-5

文献信息

• 12-Tungstophosphoric Acid Immobilized on γ-Fe₂O₃@SiO₂ Core–Shell Nanoparticles: An Effective Solid Acid Catalyst for the Synthesis of Indole Derivatives in Water
  作者：Ezzat Rafiee、Sara Eavani、Bizhan Malaekeh-Nikouei

  DOI：10.1246/cl.2012.438

  日期：2012.4.5

  12-Tungstophosphoric acid immobilized on γ-Fe2O3@SiO2 core–shell nanoparticles was used as novel solid acid catalyst for the synthesis of various bis(indolyl)methanes and β-functionalized indoles in water. The catalyst can be recovered simply using an external magnetic field and reused several times without appreciable loss of its catalytic activity.

  固定在γ-Fe2O3@SiO2核壳纳米粒子上的12-钨磷酸被用作新型固体酸催化剂，用于在水中合成各种双（吲哚基）甲烷和β官能化吲哚。该催化剂只需利用外部磁场就可回收并重复使用多次，其催化活性不会明显减弱。
• Multicomponent reactions studies: Yonemitsu-type trimolecular condensations promoted by Ti(IV) derivatives
  作者：Stéphane Gérard、Andrea Renzetti、Bérangère Lefevre、Antonella Fontana、Paolo de Maria、Janos Sapi

  DOI：10.1016/j.tet.2010.02.025

  日期：2010.4

  We have developed a Ti(IV)/Et3N-promoted trimolecular condensation of aromatic heterocycles (furan, pyrrole, imidazole, indole) with aldehydes and active methylene compounds. In the case of indole and methyl acetoacetate the reaction afforded three-component products or tricyclic cyclopenta[b]indole derivative, depending on the reaction conditions. In both cases, NMR analysis evidenced that titanium

  我们已经开发出Ti（IV）/ Et 3 N促进的芳香族杂环（呋喃，吡咯，咪唑，吲哚）与醛和活性亚甲基化合物的三分子缩合。在吲哚和乙酰乙酸甲酯的情况下，根据反应条件，反应得到三组分产物或三环环戊[ b ]吲哚衍生物。在这两种情况下，NMR分析都表明烯醇钛是反应中涉及的反应性物质。
• Starch as a green source for Fe3O4@carbon core–shell nanoparticles synthesis: a support for 12-tungstophosphoric acid, synthesis, characterization, and application as an efficient catalyst
  作者：Ezzat Rafiee、Maryam Khodayari

  DOI：10.1007/s11164-015-2229-5

  日期：2016.4

  12-Tungstophosphoric acid (PW) immobilized on carbon-coated Fe3O4 nanoparticles (Fe3O4@C-PW) was prepared through a combination of hydrothermal and chemical co-precipitation. The intermediate carbon layer, which was produced from starch as a green material, protects the magnetic core and also improves the dispersion and catalytic activity of the nanoparticles. Characterization of this catalyst was investigated by high resolution transmission electron microscopy (HRTEM), Fourier transform infrared spectroscopy (FT-IR), vibrating sample magnetometry, and the acidic properties were studied by NH3-temperature programmed desorption and potentiometric titration. The HRTEM image showed that the catalyst had a well-defined core–shell structure with an average particle size of 50 nm. The characterization data derived from FT-IR reveal that basic structure and geometry of the Keggin anion are preserved after synthesis of Fe3O4@C-PW. The as-prepared Fe3O4@C-PW was used as a nanocatalyst for the synthesis of various bis(indolyl)methanes and β-functionalized indoles in water. The catalyst can be recovered simply using an external magnetic field and reused several times without appreciable loss of its catalytic activity.

  12-磷钨酸（PW）负载在碳涂层Fe3O4纳米颗粒（Fe3O4@C-PW）上的制备通过水热和化学共沉淀的结合进行。由淀粉制成的中间碳层作为绿色材料，保护了磁性核心，并改善了纳米颗粒的分散性和催化活性。通过高分辨率透射电子显微镜（HRTEM）、傅里叶变换红外光谱（FT-IR）、振动样品磁力仪对该催化剂进行了表征，酸性特性则通过氨-程序升温脱附和电位滴定进行了研究。HRTEM图像显示，催化剂具有明确的核-壳结构，平均粒径为50纳米。FT-IR的表征数据表明，在合成Fe3O4@C-PW后，Keggin阴离子的基本结构和几何形状得以保留。合成的Fe3O4@C-PW作为纳米催化剂用于水中合成各种双（吲哚基）甲烷和β-功能化吲哚。该催化剂可以通过外部磁场简单回收，并可多次重复使用，而催化活性几乎没有显著损失。