Methyl 2-[acetamido-(4-methylphenyl)methyl]-3-oxobutanoate | 195969-38-1

• 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: Methyl 2-[acetamido-(4-methylphenyl)methyl]-3-oxobutanoate
• CAS: 195969-38-1
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: OHLPAAUZMWFMQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  Methyl 2-[acetamido-(4-methylphenyl)methyl]-3-oxobutanoate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 2-(Acetylamino-p-tolyl-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：

  乙酰乙酸甲酯 、 N-[1-benzotriazol-1-yl-1-(4-methylphenyl)methyl]acetamide 在 samarium (III) iodide 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到Methyl 2-[acetamido-(4-methylphenyl)methyl]-3-oxobutanoate
  参考文献：
  名称：

  Samarium Triiodide–Catalyzed Formation of Mannich‐Type Products by Amidoalkylation of 1,3‐Dicarbonyl Compounds

  摘要：

  DOI：

  10.1080/00397910701569569

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。
• 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。
• A simpler and greener protocol for the preparation of β-acetylamino ketones by a one-pot reaction of aryl aldehydes, enolisable ketones, acetyl chloride and acetonitrile in the presence of zeolite Hβ as a reusable catalyst
  作者：Ramakrishna P. Bhat、Vivek P. Raje、Varughese M. Alexander、Sachin B. Patil、Shriniwas D. Samant

  DOI：10.1016/j.tetlet.2005.05.018

  日期：2005.7

  β-Acetylamino ketones have been obtained in a one-pot coupling of an aldehyde with an enolisable ketone, acetyl chloride and acetonitrile in the presence of zeolite Hβ as catalyst at room temperature (26–28 °C). The procedure has the advantages of mild workup, circumvention of high temperature and inert atmosphere. The catalyst was found to be recyclable.

  在室温（26–28°C）下，在沸石Hβ作为催化剂的情况下，通过醛与可酮化的酮，乙酰氯和乙腈的一锅偶联制得β-乙酰氨基酮。该程序具有后处理温和，规避高温和惰性气氛的优点。发现该催化剂是可回收的。
• Iqbal, Javed; Mukhopadhyay, Manoj; Das, Bhaskar C., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1997, vol. 36, # 6, p. 498 - 506
  作者：Iqbal, Javed、Mukhopadhyay, Manoj、Das, Bhaskar C.、Rajesh、De, Asit、Sanghi, Rashmi、Jain, Swati、Nandy, Jyoti P.

  DOI：——

  日期：——
• KAl (SO₄)₂.12H₂O or KHSO₄: Efficient and Inexpensive Catalysts for the One-Pot Synthesis of β-Acetamido Ketones by Dakin–West Reaction
  作者：Majid M. Heravi、Masoumeh Zakeri、Narges Mohammadi、Hoda Haghi

  DOI：10.1080/15533174.2011.609514

  日期：2012.2.1

  Aromatic aldehydes were reacted in a vessel with enolizable ketones, acetonitrile, and acetyl chloride at ambient temperature in the presence of KAl(SO4)(2)center dot 12H(2)O to furnish the corresponding beta-acetamido ketones in excellent yields. KHSO4 has also been used as another catalyst for this reaction at room temperature. Key features of this methodology are operational simplicity, mild reaction conditions, and excellent yields.