ethyl 2-(acetamido(phenyl)-methyl)-3-oxobutanoate | 92653-04-8

• 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: ethyl 2-(acetamido(phenyl)-methyl)-3-oxobutanoate
• 英文别名: ethyl 2-(acetamido(phenyl)methyl)-3-oxobutanoate；2-(α-acetylamino-benzyl)-acetoacetic acid ethyl ester；2-(α-Acetylamino-benzyl)-acetessigsaeure-aethylester；Ethyl 2-[(acetylamino)(phenyl)methyl]-3-oxobutanoate；ethyl 2-[acetamido(phenyl)methyl]-3-oxobutanoate
• CAS: 92653-04-8
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: GMHTZOWJZBVCAF-UHFFFAOYSA-N

物化性质

• 熔点：
  95-96 °C
• 沸点：
  475.1±45.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  7
• 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：

  ethyl 2-(acetamido(phenyl)-methyl)-3-oxobutanoate 在 盐酸 、 lithium hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 39.0h， 生成 3-(Pent-4-enoylamino)-3-phenylpropanoic acid
  参考文献：
  名称：

  Synthesis of a cyclic pseudo 310 helical structure from a β-amino acid-l-proline derived tripeptide via a ring closing metathesis reaction

  摘要：

  The combination of homo-phenylglycine (Hpg) and proline leads to the formation of a beta-turn mimic, which can be transformed into a cyclic peptide using a ring closing metathesis reaction. The presence of the pentenoyl and allyl groups at the terminus of the peptide leads to the concomitant formation of a linker surrogate fourth amino acid (6-amino-4-hexenoic acid; Aha) during the cyclization. The cyclic peptide is unique in having a pseudo 3(10) helical structure. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01239-x
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 N-(1-benzotriazoyl-1-phenylmethyl)acetamide 在 samarium (III) iodide 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到ethyl 2-(acetamido(phenyl)-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

• 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。
• Iodine as an Efficient Catalyst for One-Pot Multicomponent Synthesis of β-Acetamido Ketones
  作者：Biswanath Das、K. Reddy、R. Ramu、P. Thirupathi、B. Ravikanth

  DOI：10.1055/s-2006-944208

  日期：2006.7

  Iodine efficiently catalyzes the three-component coupling of aromatic aldehydes, enolizable ketones or keto esters, and acetonitrile in the presence of acetyl chloride to afford β-acetamido ketones in good yields at room temperature.

  碘在乙酰氯存在下有效地催化芳香醛、烯醇化酮或酮酯和乙腈的三组分偶联，以在室温下以良好的收率提供 β-乙酰胺酮。
• One-pot multicomponent synthesis of β-acetamidoketones catalysed by <i>p</i>TSA¹
  作者：Biswanath Das、Kongara Ravinder Reddy、Yallamalla Srinivas、Rathod Aravind Kumar

  DOI：10.1139/v07-062

  日期：2007.7.1

  A catalytic amount of pTSA has been found to be effective to carry out a one-pot three-component coupling of aromatic aldehydes, enolizable ketones or ketoesters, and acetonitrile in the presence of acetyl chloride to afford β-acetamidoketones in high yields. Short reaction times and inexpensive catalyst are main advantages of this protocol.Key words: β-acetamidoketone, pTSA, multicomponent reaction, diastereoselectivity.

  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
• Reactions of Bisamides. V. Synthesis of Derivatives of β-Ayrl-β-Amino Acids
  作者：Gjorgje Stefanovic´、Slavko Mihajlovic´、Milutin Stefanovic´

  DOI：10.1021/jo50017a001

  日期：1953.11
• Synthesis of small cyclic peptides via intramolecular Heck reactions
  作者：P Rajamohan Reddy、V Balraju、G.R Madhavan、Biswadip Banerji、Javed Iqbal

  DOI：10.1016/s0040-4039(02)02573-x

  日期：2003.1