2-[Acetylamino-(4-chloro-phenyl)-methyl]-3-oxo-butyric acid methyl ester | 170034-50-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[Acetylamino-(4-chloro-phenyl)-methyl]-3-oxo-butyric acid methyl ester
• 英文别名: Methyl 2-[acetamido-(4-chlorophenyl)methyl]-3-oxobutanoate
• CAS: 170034-50-1
• 化学式: C₁₄H₁₆ClNO₄
• 分子量: 297.738
• InChiKey: ZKEPZAYMFKFGQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[Acetylamino-(4-chloro-phenyl)-methyl]-3-oxo-butyric acid methyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 2-[Acetylamino-(4-chloro-phenyl)-methyl]-3-hydroxy-butyric acid methyl ester
  参考文献：
  名称：

  Iqbal, Javed; Mukhopadhyay, Manoj; Das, Bhaskar C., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 6, p. 498 - 506

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯苯甲醛 、 乙酰乙酸甲酯 、 乙酰氯 在 对甲苯磺酸 乙腈 作用下， 反应 5.25h， 以86%的产率得到2-[Acetylamino-(4-chloro-phenyl)-methyl]-3-oxo-butyric acid methyl ester
  参考文献：
  名称：

  One-pot multicomponent synthesis of β-acetamidoketones catalysed by pTSA¹

  摘要：

  研究发现，在乙酰氯存在下，催化量 pTSA 可有效地将芳香醛、可烯化的酮或酮酯与乙腈进行一锅三组分偶联反应，从而高产率地得到 β-乙酰胺酮。关键字：β-乙酰胺酮 pTSA 多组分反应 非对映选择性

  DOI：

  10.1139/v07-062

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。
• 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。
• CeCl3·7H2O: an efficient and reusable catalyst for the preparation of β-acetamido carbonyl compounds by multi-component reactions (MCRs)
  作者：Abu T. Khan、Lokman H. Choudhury、Tasneem Parvin、Md. Asif Ali

  DOI：10.1016/j.tetlet.2006.09.041

  日期：2006.11

  A convenient method for the preparation of β-acetamido carbonyl compounds is described by multi-component reactions of aromatic aldehydes, enolizable ketones or β-keto esters and acetonitrile in the presence of acetyl chloride and 10 mol % CeCl3·7H2O at room temperature.

  在室温下，在乙酰氯和10 mol％CeCl 3 ·7H 2 O存在下，芳族醛，可烯化的酮或β-酮酸酯与乙腈的多组分反应描述了一种方便的制备β-乙酰氨基羰基化合物的方法。温度。
• Bulk and Activated Carbon-Supported Tungstophosphoric Acid as Recyclable and Green Catalyst for One-Pot Synthesis of<i>β</i>-Acetamido Ketones and Esters
  作者：Fatemeh F. Bamoharram、Ali Ahmadpour、Majid M. Heravi、Mohammad J. Sane Charkhi

  DOI：10.1155/2011/741328

  日期：——

  A rapid and efficient one-pot method for the synthesis ofβ-acetamido ketones/esters has been developed in the presence of bulk tungstophosphoric acid and its supported forms on activated carbon as recyclable and eco-friendly catalysts under refluxing conditions. Supported tungstophosphoric acid catalysts containing the same amount of heteropoly acid yielded much higher conversion than bulk form.

  已开发出一种快速高效的一锅法合成β-乙酰胺基酮/酯的方法，在反流条件下，利用大块状磷钨酸和其在活性炭上支撑形式作为可回收和环保催化剂。含有相同量杂多酸的支撑磷钨酸催化剂产生比大块形式更高的转化率。