N-(1-(4-chlorophenyl)-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-chlorophenyl)-3-oxo-3-phenylpropyl)acetamide
• 英文别名: β-acetamido-β-(4-chlorophenyl)propiophenone；N-[1-(4-chlorophenyl)-3-oxo-3-phenylpropyl]acetamide
• 化学式: C₁₇H₁₆ClNO₂
• 分子量: 301.773
• InChiKey: SUGCOOMZDRCCQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 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：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1-(4-chlorophenyl)-3-oxo-3-phenylpropyl)acetamide 在 potassium iodide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.0h， 以75%的产率得到[4-(4-chlorophenyl)-2-methyl-4,5-dihydrooxazol-5-yl]phenylmethanone
  参考文献：
  名称：

  Electrosynthesis of Trisubstituted 2-Oxazolines via Dehydrogenative Cyclization of β-Amino Arylketones

  摘要：

  An electrochemically intramolecular functionalization of C-(sp(3))-H bonds with masked oxygen nucleophiles was developed. With IU as the catalyst and electrolyte, diverse trisubstituted 2-oxazolines were constructed in good to excellent yields. This newly developed electrochemical dehydrogenalive approach features external oxidant-free and additive-free conditions.

  DOI：

  10.1021/acs.orglett.8b00165
• 作为产物：
  描述：

  苯乙酮 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 N-(1-(4-chlorophenyl)-3-oxo-3-phenylpropyl)acetamide
  参考文献：
  名称：

  氯化铁（III）催化方便地一锅合成β-乙酰氨基羰基化合物

  摘要：

  乙醛，可烯醇化的酮或1,3-二羰基化合物，乙腈/苄腈和乙酰氯的一锅多组分反应描述了一种温和，廉价的方法，用于使用FeCl 3 ·6H 2 O制备β-乙酰胺基羰基化合物。，以及高效的催化剂。还说明了底物以及取代基对于多组分反应与Knoevenagel缩合的影响。该方法的主要特点是操作简便，反应条件温和且收率高。

  DOI：

  10.1016/j.tet.2007.04.019

文献信息

• 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。
• SBA-15-Pr–SO3H: An efficient, environment friendly and recyclable heterogeneous nanoreactor catalyst for the one-pot multicomponent synthesis of β-acetamido ketones
  作者：KIUMARS BAHRAMI、MOHAMMAD M KHODAEI、PEYMAN FATTAHPOUR

  DOI：10.1007/s12039-014-0762-1

  日期：2015.1

  multi-component condensation of aromatic aldehydes, ketones and acetonitrile in the presence of acetyl chloride at 80°C to afford β-acetamido ketones in excellent yields. The catalyst can be recovered and recycled for subsequent reactions without any appreciable loss of efficiency. SBA-15-Pr–SO3H as nanoreactor catalyzes the multicomponent condensation of aromatic aldehydes, ketones, and acetonitrile

  SBA-15-Pr–SO 3 H在80°C的乙酰氯存在下，催化芳香醛，酮和乙腈的多组分缩合反应，从而以优异的收率得到β-乙酰胺基酮。催化剂可被回收并再循环用于随后的反应，而没有任何明显的效率损失。 SBA-15-Pr–SO 3 H作为纳米反应器，在80°C的乙酰氯存在下，催化芳香醛，酮和乙腈的多组分缩合反应，从而以优异的收率得到β-乙酰胺基酮。
• 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。