N-[1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl]acetamide

• 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-methoxyphenyl)-3-oxo-3-phenylpropyl]acetamide
• 英文别名: β‐acetamido‐β‐(4‐methoxyphenyl)propiophenone；β-acetamido-β-(4-methoxyphenyl)propiophenone；N-[1-(4-methoxy-phenyl)-3-oxo-3-phenyl-propyl]-acetamide；N-[1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl]-acetamide；N-[1-(4-methoxyphenyl)-3-oxo-3 phenylpropyl]acetamide；N-{1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl}acetamide
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: RXDMLDCNPQZFID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 乙酰氯 、 苯乙酮 在 硫酸钴水合物 、 乙腈 作用下， 反应 2.0h， 以91%的产率得到N-[1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl]acetamide
  参考文献：
  名称：

  Efficient Synthesis of β-Acetamido Ketones Catalyzed by Cobalt Sulfate Heptahydrate Under Ultrasound Irradiation

  摘要：

  在七水硫酸钴催化下，芳香醛、苯乙酮和乙酰氯在乙腈中通过一锅多组分反应偶联合成了β-乙酰氨基酮，在 25-28 °C的温度下产量极佳，为这些化合物的高效合成提供了可能。与回流条件下的反应相比，使用超声波提高了反应速率。

  DOI：

  10.2174/157017812799304088

文献信息

• VB1–Al2O3-catalyzed one-pot condensation of aromatic ketone, aromatic aldehyde, and amide
  作者：Min Lei、Lei Ma、Lihong Hu

  DOI：10.1016/j.tetlet.2010.07.008

  日期：2010.9

  A novel and green approach for the efficient synthesis of β-amido ketones using VB1–Al2O3 as a heterogeneous catalyst for the first time from an aldehyde, enolizable ketones, and an amide in EtOH is described. The present methodology has several advantages from the economical and environmental points of view, such as simple procedure, low catalyst loading, high atom economy, and good yields.

  描述了一种新颖且绿色的方法，首次使用VB 1 -Al 2 O 3作为多相催化剂从乙醛，可烯化的酮和酰胺在EtOH中有效合成β-酰胺基酮。从经济和环境的观点来看，本方法具有若干优点，例如操作简单，催化剂用量低，原子经济性高和产率高。
• Synthesis of Mannich type products via a three-component coupling reaction
  作者：Ghanshyam Pandey、Ravi P. Singh、Ashish Garg、Vinod K. Singh

  DOI：10.1016/j.tetlet.2005.01.118

  日期：2005.3

  The reactions of alkyl nitriles, acetyl chloride, aldehydes and β-ketoesters or simple ketones was studied for the one-pot synthesis of β-acetamido carbonyl compounds. It was observed that the reaction proceeds in the absence of Lewis acids. However, a Lewis acid catalyzes the reaction and several were tested. It was found that whereas Cu(OTf)2 is suitable for the coupling of β-ketoesters with aldehydes

  为一锅法合成β-乙酰氨基羰基化合物，研究了烷基腈，乙酰氯，醛和β-酮酸酯或简单酮的反应。观察到反应在不存在路易斯酸的情况下进行。但是，路易斯酸催化该反应，并对其进行了测试。发现Cu（OTf）2适合将β-酮酸酯与醛偶联，而Sc（OTf）3最适合酮。根据中间体的分离和表征，提出了一种可能的机制。
• 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。
• Facile and diastereoselective synthesis of β-acetamido ketones and keto esters via direct Mannich-type reaction
  作者：Hui Mao、Jieping Wan、Yuanjiang Pan

  DOI：10.1016/j.tet.2008.11.071

  日期：2009.1

  A Mannich-type three-component reaction involving aldehydes, acetamide, and enolizable ketones or β-keto esters for the preparation of β-acetamido carbonyl compounds in the presence of TMSCl is described. This newly developed protocol is operationally convenient, widely applicable, and highly diastereoselective.

  描述了用于在TMCSC1存在下制备β-乙酰氨基羰基化合物的涉及醛，乙酰胺和可烯醇化的酮或β-酮酯的曼尼希型三组分反应。该新开发的协议操作方便，适用范围广且具有非对映选择性。