N-Formyl-α-aminobuttersaeuremethylester | 141971-14-4

• 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: N-Formyl-α-aminobuttersaeuremethylester
• 英文别名: Methyl 2-formamidobutanoate
• CAS: 141971-14-4
• 化学式: C₆H₁₁NO₃
• 分子量: 145.158
• InChiKey: KQYCKXPRUOZRKK-UHFFFAOYSA-N

物化性质

• 沸点：
  279.5±23.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Formyl-α-aminobuttersaeuremethylester 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以77%的产率得到(+/-)-methyl 2-isocyanobutanoate
  参考文献：
  名称：

  A Resource-Efficient and Highly Flexible Procedure for a Three-Component Synthesis of 2-Imidazolines

  摘要：

  A multicomponent reaction between alpha-acidic isonitriles, primary amines, and carbonyl compounds was studied using 14 different solvents. Depending on the isocyanide that was used, optimal yields for the three-component synthesis of 2H-2-imidazolines were observed in different solvents. The solvents could be used as purchased, and in situ preformation of the imine was not required. By selecting the appropriate solvent, it was possible to considerably expand the range of compatible isocyanides toward less alpha-acidic isocyanides. Further process simplification was achieved by performing the reaction at higher concentrations and avoiding purification by column chromatography, resulting in a fast, easy to perform, and resource-efficient protocol for this three-component reaction.

  DOI：

  10.1021/jo070840x
• 作为产物：
  描述：

  (Z)-Methyl 2-(formylamino)-2-butenoate 在 hydrogen 作用下， 以100%的产率得到N-Formyl-α-aminobuttersaeuremethylester
  参考文献：
  名称：

  氨基保护基在受保护的脱氢氨基酸的副氢化中的作用

  摘要：

  使在氨基和羧酸酯部分具有不同保护基并且在双键具有不同取代基的一系列脱氢氨基酸与对氢反应。在1 H NMR光谱中观察到的副氢诱导极化（PHIP）效应强烈依赖于氨基保护基。DFT计算使我们能够建立反应中间体的结构（其能量取决于酰胺取代基）与观察到的PHIP模式之间的关系。

  DOI：

  10.1021/acs.jpca.5b06802

文献信息

• Heyns,K.; Gruetzmacher,H.-F., Zeitschrift fur Naturforschung. Teil B. Anorganische Chemie, organische Chemie, Biochemie, Biophysik, Biologie, 1961, vol. 16, p. 293 - 298
  作者：Heyns,K.、Gruetzmacher,H.-F.

  DOI：——

  日期：——
• Hromatka; Eiles, Monatshefte fur Chemie, 1948, vol. 78, p. 133
  作者：Hromatka、Eiles

  DOI：——

  日期：——
• A Resource-Efficient and Highly Flexible Procedure for a Three-Component Synthesis of 2-Imidazolines
  作者：Niels Elders、Rob F. Schmitz、Frans J. J. de Kanter、Eelco Ruijter、Marinus B. Groen、Romano V. A. Orru

  DOI：10.1021/jo070840x

  日期：2007.8.1

  A multicomponent reaction between alpha-acidic isonitriles, primary amines, and carbonyl compounds was studied using 14 different solvents. Depending on the isocyanide that was used, optimal yields for the three-component synthesis of 2H-2-imidazolines were observed in different solvents. The solvents could be used as purchased, and in situ preformation of the imine was not required. By selecting the appropriate solvent, it was possible to considerably expand the range of compatible isocyanides toward less alpha-acidic isocyanides. Further process simplification was achieved by performing the reaction at higher concentrations and avoiding purification by column chromatography, resulting in a fast, easy to perform, and resource-efficient protocol for this three-component reaction.
• The Role of the Amino Protecting Group during Parahydrogenation of Protected Dehydroamino Acids
  作者：Erika Cerutti、Alessandra Viale、Carlo Nervi、Roberto Gobetto、Silvio Aime

  DOI：10.1021/acs.jpca.5b06802

  日期：2015.11.19

  A series of dehydroamino acids endowed with different protective groups at the amino and carboxylate moieties and with different substituents at the double bond have been reacted with parahydrogen. The observed ParaHydrogen Induced Polarization (PHIP) effects in the 1H NMR spectra are strongly dependent on the amino protecting group. DFT calculations allowed us to establish a relationship between the

  使在氨基和羧酸酯部分具有不同保护基并且在双键具有不同取代基的一系列脱氢氨基酸与对氢反应。在1 H NMR光谱中观察到的副氢诱导极化（PHIP）效应强烈依赖于氨基保护基。DFT计算使我们能够建立反应中间体的结构（其能量取决于酰胺取代基）与观察到的PHIP模式之间的关系。