N-(1-(4-nitrophenyl)-3-oxo-3-phenylpropyl)acetamide | 155793-24-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-(1-(4-nitrophenyl)-3-oxo-3-phenylpropyl)acetamide
• 英文别名: β‐acetamido‐β‐(4‐nitrophenyl)propiophenone；β-acetamido-β-(4-nitrophenyl)-propiophenone；β-acetamido-β-(4-nitrophenyl)propiophenone；N-[1-(4-nitro-phenyl)-3-oxo-3-phenyl-propyl]-acetamide；N-[1-(4-nitrophenyl)-3-oxo-3-phenyl-propyl]acetamide；N-[1-(4-nitrophenyl)-3-oxo-3-phenylpropyl]acetamide
• CAS: 155793-24-1
• 化学式: C₁₇H₁₆N₂O₄
• 分子量: 312.325
• InChiKey: NUXWCPXBWJKFHV-UHFFFAOYSA-N

物化性质

• 熔点：
  148-149 °C
• 沸点：
  571.2±50.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  92
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(1-(4-nitrophenyl)-3-oxo-3-phenylpropyl)acetamide 在 叔丁基过氧化氢 、 碘 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以67%的产率得到(2-methyl-4-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl)(phenyl)methanone
  参考文献：
  名称：

  I₂-Catalyzed C–O Bond Formation and Dehydrogenation: Facile Synthesis of Oxazolines and Oxazoles Controlled by Bases

  摘要：

  A general method for the synthesis of oxazolines and oxazoles was developed through I-2-catalyzed C-O bond formation and dehydrogenation with the same oxidant, TBHP. By simply tuning reaction bases, either oxazolines or oxazoles were selectively produced from beta-acylamino ketones.

  DOI：

  10.1021/acs.orglett.5b01933
• 作为产物：
  描述：

  苯甲醛 、 乙酰氯 、 对硝基苯乙酮 在 1,4-bis(3-sulfopropyl)piperazinium bis(trifluoromethanesulfonate) 、 乙腈 作用下， 反应 1.5h， 以91%的产率得到N-(1-(4-nitrophenyl)-3-oxo-3-phenylpropyl)acetamide
  参考文献：
  名称：

  Novel bi-SO3H-functionalized ionic liquids based on piperazinium: Highly efficient and recyclable catalysts for the synthesis of β-acetamido ketones

  摘要：

  A series of novel bi-SO3H-functionalized ionic liquids were synthesized and acted as catalysts for the synthesis of beta-acetamido ketones. Compared with traditional single-SO3H-functionalized ionic liquids, less amount of catalysts, higher yields and shorter reaction time are the key features of this methodology. Hammett function values and the minimum-energy geometries of bi-SO3H-functionalized ILs were calculated and the results revealed that the acidities and catalytic activities of ILs in synthesis of beta-acetamido ketones were influenced by their structures. The IL[(PS)(2)pi][OTf](2) with the shortest H-O bond distance had the strongest acidity and the highest catalytic activity. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2012.09.023

文献信息

• One-pot preparation of β-amido ketones/esters in a three-component condensation reaction using magnesium hydrogensulfate as an effective and reusable catalyst
  作者：Hamid Reza Shaterian、Asghar Hosseinian、Majid Ghashang

  DOI：10.1139/v08-013

  日期：2008.5.1

  three-component condensation of an aryl aldehyde, an enolizable ketone or β-keto ester, acetyl chloride, and acetonitrile or benzonitrile in the presence of magnesium hydrogensulfate as an active, recoverable, and reusable green catalyst is described for the synthesis of β-amido ketones/esters at room temperature. The key features of this methodology are simplicity, mild reaction conditions, and high

  在硫酸氢镁作为活性、可回收和可重复使用的绿色催化剂存在下，芳醛、可烯醇化酮或 β-酮酯、乙酰氯和乙腈或苯甲腈的一锅三组分缩合反应被描述用于在室温下合成 β-酰胺酮/酯。该方法的主要特点是简单、反应条件温和、收率高至极好。关键词：多组分反应、硫酸氢镁、多相催化剂、β-酰胺基酮/酯、温和条件。
• One-Pot Multicomponent Synthesis of β-Acetamido Ketones Based on BiCl₃ Generated in situ from the Procatalyst BiOCl and Acetyl Chloride
  作者：Rina Ghosh、Swarupananda Maiti、Arijit Chakraborty

  DOI：10.1055/s-2004-836024

  日期：——

  Aromatic aldehydes react in one pot at room temperature with enolizable ketones and acetonitrile in the presence of acetyl chloride and catalytic amount of BiOCl producing the corresponding β-acetamido ketones in very high to excellent yields. BiCl3 ­generated in situ from BiOCl and acetyl chloride catalyzes the ­multicomponent reaction.

  芳香醛在室温下一锅反应，与可烯醇化的酮和乙腈在醋酸氯和催化量的BiOCl的存在下，产生对应的β-乙酰氨基酮，产率非常高到优异。BiOCl与醋酸氯原位产生的BiCl3催化了多组分反应。
• ZrOCl2·8H2O: an efficient Lewis acid catalyst for the one-pot multicomponent synthesis of β-acetamido ketones
  作者：Rina Ghosh、Swarupananda Maiti、Arijit Chakraborty、Santu Chakraborty、Alok K. Mukherjee

  DOI：10.1016/j.tet.2006.02.037

  日期：2006.4

  Aromatic aldehydes were reacted in one-pot with enolisable ketones, acetonitrile and acetyl chloride at ambient temperature in the presence of ZrOCl2·8H2O to furnish the corresponding β-acetamido ketones in very good to excellent yields. X-ray crystallographic analysis of one anti-β-acetamido ketone exhibited a two-dimensional supramolecular framework by a combination of N–H⋯O, C–H⋯O and C–H⋯π (arene)

  在环境温度下，在ZrOCl 2 ·8H 2 O的存在下，使芳香醛与可固化的酮，乙腈和乙酰氯一锅反应，以非常好的至极好的收率提供相应的β-乙酰胺基酮。一种抗-β-乙酰氨基酮的X射线晶体学分析显示了N–H⋯O，C–H⋯O和C–H⋯π（芳烃）氢键的组合，具有二维超分子构架。
• CuSO₄ · 5H₂O: A Novel, Green, Reusable, and Environmentally Friendly Catalyst for the One-Pot, Four-Component Synthesis of<font>β</font>-Acetamido Carbonyl Compounds
  作者：Farahnaz K. Behbahani、Neda Doragi、Majid M. Heravi

  DOI：10.1080/00397911.2010.529354

  日期：2012.3.1

  Abstract Multicomponent reactions for the synthesis of β-acetamido carbonyl compounds have been gained considerable attention in organic synthesis. In this articles, aromatic aldehydes have been employed in a one-pot reaction with enolizable ketones, acetonitrile, benzonitrile, and acetyl chloride in the presence of copper(II) sulfate petahydrate at ambient temperature to afford the corresponding β-acetamido

  摘要 β-乙酰氨基羰基化合物的多组分反应在有机合成中受到了广泛关注。在这篇文章中，在环境温度下，在五水硫酸铜 (II) 存在下，芳香醛与可烯醇化的酮、乙腈、苄腈和乙酰氯进行一锅反应，得到相应的 β-乙酰氨基酮。产量。报告了新化合物。使用现成的五水硫酸铜 (II) 作为可重复使用和可回收的催化剂，使该过程变得非常简单、方便且环保。图形概要
• Silica-Supported Perchloric Acid (HClO₄-SiO₂): An Efficient Catalyst for the Preparation of<font>β</font>-Amido Carbonyl Compounds Using Multicomponent Reactions
  作者：Hamid Reza Shaterian、Asghar Hosseinian、Majid Ghashang

  DOI：10.1080/00397910802218728

  日期：2008.10.22

  Abstract A new, one-pot, efficient, three-component condensation of benzaldehyde derivatives, enolizable ketones, acetyl chloride, and acetonitrile or benzonitrile in the presence of silica-supported perchloric acid as an effective catalyst for the synthesis of β-amido carbonyl compounds is described. The present methodology offers several advantages, such as good yields, short reaction times, and

  摘要 在二氧化硅负载的高氯酸存在下，苯甲醛衍生物、烯醇化酮、乙酰氯和乙腈或苄腈的新型一锅高效三组分缩合反应是合成β-酰胺羰基化合物的有效催化剂。被描述。本方法提供了几个优点，例如良好的收率、较短的反应时间和简单的后处理程序。