N-Acetyl-α-methylphenylalaninmethylester | 16024-41-2

• 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-Acetyl-α-methylphenylalaninmethylester
• 英文别名: (+/-)-Methyl-2-acetamido-2-methyl-3-phenylpropionat；2-acetylamino-2-methyl-3-phenyl-propionic acid methyl ester；2-Acetylamino-2-methyl-3-phenyl-propionsaeure-methylester；Methyl 2-acetamido-2-methyl-3-phenylpropanoate；methyl 2-acetamido-2-methyl-3-phenylpropanoate
• CAS: 16024-41-2
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: YEEFCTTYYXXHLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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-Acetyl-α-methylphenylalaninmethylester 在 乙醇 、 sodium 作用下， 生成 2-amino-2-methyl-3-phenylpropan-1-ol
  参考文献：
  名称：

  α-Methyl α-Amino Acids. II.¹ Derivatives of DL-Phenylalanine

  摘要：

  DOI：

  10.1021/ja01608a046
• 作为产物：
  描述：

  2-(苯基甲基)-2-氨基丙酸甲酯 、 溶剂黄146 在 copper diacetate 作用下， 反应 6.0h， 以96%的产率得到N-Acetyl-α-methylphenylalaninmethylester
  参考文献：
  名称：

  Preparation of benzolactams by Pd(ii)-catalyzed carbonylation of N-unprotected arylethylamines

  摘要：

  研究人员开发了一种前所未有的 NH2 定向钯（II）催化季芳香族 α-氨基酯羰基化反应，生成 6 元苯内酰胺。与 5 元内酰胺相比，该反应更倾向于 6 元内酰胺。氨基周围的立体阻碍似乎是该过程成功的关键。

  DOI：

  10.1039/c0cc03478a

文献信息

• Synthesis of α-amino acid derivatives by copper(I)-catalyzed conjugate addition of grignard reagents to methyl 2-acetamidoacrylate
  作者：C. Cardellicchio、V. Fiandanese、G. Marchese、F. Naso、L. Ronzini

  DOI：10.1016/s0040-4039(00)98742-2

  日期：1985.1

  The reactions of Grignard reagents with methyl 2-acetamidoacrylate in the presence of CuI give fair to good yields of α-amino esters; the corresponding α-deutero- or α-methyl-derivatives are obtained upon quenching with D+ or CH3I, respectively.

  在CuI的存在下，格氏试剂与2-乙酰氨基丙烯酸甲酯的反应可以使α-氨基酯的收率达到中等水平。分别用D +或CH 3 I淬灭得到相应的α-氘代或α-甲基衍生物。
• Synthesis of protected, chiral α,α-disubstituted α-amino acids via a Beckmann rearrangement
  作者：Rogelio P. Frutos、Denice M. Spero

  DOI：10.1016/s0040-4039(98)00309-8

  日期：1998.4

  The synthesis of chiral, nonracemic, fully protected α,α-disubstituted α-amino acids via the Beckmann rearrangement of tosylated oximes 1 is described. The desired amino acids were obtained in good yields with excellent enantioselectivities in relatively few steps.

  描述了通过甲苯磺酸化肟1的贝克曼重排合成手性，非外消旋，完全保护的α，α-二取代的α-氨基酸。在相对较少的步骤中，以良好的对映选择性，以良好的收率获得了所需的氨基酸。
• NH₂ As a Directing Group: From the Cyclopalladation of Amino Esters to the Preparation of Benzolactams by Palladium(II)-Catalyzed Carbonylation of N-Unprotected Arylethylamines
  作者：Joan Albert、Xavier Ariza、Teresa Calvet、Mercé Font-Bardia、Jordi Garcia、Jaume Granell、Andrea Lamela、Blanca López、Manuel Martinez、Laura Ortega、Aleix Rodriguez、David Santos

  DOI：10.1021/om301140t

  日期：2013.1.28

  An unusual NH2-directed Pd(II)-catalyzed carbonylation of quaternary aromatic alpha-amino esters to yield benzolactams has been developed. The steric hindrance around the amino group is pivotal for the success of the process. The stoichiometric cyclometalation of a variety amino esters has been studied in order to evaluate the influence of the different variables (size of the metallacycle, aromatic ring substituents, and steric bulk) in the process, and a complete kinetico-mechanistic study of the cyclopalladation process has been carried out. The experimental results indicate that the full substitution of the carbon in the alpha position of the amino esters plays an important role in their cyclopalladation reaction. The reaction shows a strong bias toward six-membered lactams over the five-membered analogues, which can be explained by a greater reactivity of the six-membered palladacycles.
• Ghosh et al., Journal of the Indian Chemical Society, 1957, vol. 34, p. 417,422
  作者：Ghosh et al.

  DOI：——

  日期：——
• α-Methyl α-Amino Acids. II.¹ Derivatives of DL-Phenylalanine
  作者：Gustav A. Stein、Hermann A. Bronner、K. Pfister

  DOI：10.1021/ja01608a046

  日期：1955.2.1