(2S)-2-[(tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropanamide | 1428736-37-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-2-[(tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropanamide
• 英文别名: tert-butyl (S)-(1-amino-2-methyl-1-oxo-3-phenylpropan-2-yl)carbamate；tert-butyl N-[(2S)-1-amino-2-methyl-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 1428736-37-1
• 化学式: C₁₅H₂₂N₂O₃
• 分子量: 278.351
• InChiKey: KIGLZLYHQOWHNT-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropanamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以93%的产率得到(2S)-2-amino-2-methyl-3-phenylpropanamide
  参考文献：
  名称：

  Enantiocatalytic activity of substituted 5-benzyl-2-(pyridine-2-yl)imidazolidine-4-one ligands

  摘要：

  Currently, asymmetric synthesis represents one of the main streams of organic synthesis. Although an extensive research has been carried out in this area, the synthesis of chiral compounds with the required enantiomeric purity is still a challenging issue. Herein, we focus on the preparation of new enantioselective catalysts based on pyridine-imidazolidinones. The substituted 5-benzyl-2-(pyridine-2-yl)imidazolidine-4-ones 5-8 were prepared by condensation of chiral amino acid amides (alpha-methylDOPA and alpha-methylphenylalanine) with 2-acetylpyridine and pyridine-2-carbaldehyde. The individual isomers of the described ligands 5-8 were separated chromatographically. The copper(II) complexes of these chiral ligands were studied as enantioselective catalysts for the asymmetric Henry reaction of substituted aldehydes with nitromethane or nitroethane. The ligands containing a methyl group at the 2-position of the imidazolidinone ring 6a and 8a exhibit a high degree of enantioselectiyity (up to 91% ee). The nitroaldols derived from nitroethane (2-nitropropan-1-ols) were obtained with a comparable enantiomeric purity to derivatives of 2-nitroethanol. This group of ligands represents a new and promising class of enantioselective catalysts, which deserve further attention. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.007
• 作为产物：
  描述：

  alpha-甲基-DL-苯丙氨酸 在 cinchonidine 、 氯甲酸乙酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 168.12h， 生成 (2S)-2-[(tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropanamide
  参考文献：
  名称：

  Enantiocatalytic activity of substituted 5-benzyl-2-(pyridine-2-yl)imidazolidine-4-one ligands

  摘要：

  Currently, asymmetric synthesis represents one of the main streams of organic synthesis. Although an extensive research has been carried out in this area, the synthesis of chiral compounds with the required enantiomeric purity is still a challenging issue. Herein, we focus on the preparation of new enantioselective catalysts based on pyridine-imidazolidinones. The substituted 5-benzyl-2-(pyridine-2-yl)imidazolidine-4-ones 5-8 were prepared by condensation of chiral amino acid amides (alpha-methylDOPA and alpha-methylphenylalanine) with 2-acetylpyridine and pyridine-2-carbaldehyde. The individual isomers of the described ligands 5-8 were separated chromatographically. The copper(II) complexes of these chiral ligands were studied as enantioselective catalysts for the asymmetric Henry reaction of substituted aldehydes with nitromethane or nitroethane. The ligands containing a methyl group at the 2-position of the imidazolidinone ring 6a and 8a exhibit a high degree of enantioselectiyity (up to 91% ee). The nitroaldols derived from nitroethane (2-nitropropan-1-ols) were obtained with a comparable enantiomeric purity to derivatives of 2-nitroethanol. This group of ligands represents a new and promising class of enantioselective catalysts, which deserve further attention. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.007

文献信息

• 2,4,6-Substituted Pyridyl Derivative Compounds Useful as Beta-Secretase Inhibitors for the Treatment of Alzheimer's Disease
  申请人：Barrow C. James

  公开号：US20080015233A1

  公开（公告）日：2008-01-17

  The present invention is directed to 2,4,6-substituted pyridyl derivative compounds which are inhibitors of the beta-secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases in which the beta-secretase enzyme is involved.

  本发明涉及2,4,6-取代吡啶衍生物化合物，其是beta-分泌酶酶的抑制剂，可用于治疗涉及beta-分泌酶酶的疾病，如阿尔茨海默病。本发明还涉及包含这些化合物的制药组合物以及这些化合物和组合物在涉及beta-分泌酶酶的这种疾病的治疗中的使用。
• Highly Sterically Hindered Peptide Bond Formation between α,α-Disubstituted α-Amino Acids and <i>N</i>-Alkyl Cysteines Using α,α-Disubstituted α-Amidonitrile
  作者：Xiaoling Wang、Jing Li、Yujiro Hayashi

  DOI：10.1021/jacs.2c02993

  日期：2022.6.15

  sterically hindered peptides, research on peptides bearing an amide bond between an α,α-disubstituted α-amino acid and an N-alkyl α-amino acid remains underexplored because of the lack of an efficient synthetic approach. Herein, we describe a high-yielding synthetic method to access such extremely sterically hindered peptide bonds between amino acids. The reaction takes place between a peptide with an α,α-disubstituted

  肽和蛋白质在学术界和工业界的许多领域引起了极大的关注。将不常见的氨基酸如 α,α-二取代的 α-氨基酸或N-烷基 α-氨基酸引入正常的肽骨架中是一种广泛利用且有用的工具，可用于修饰诸如构象、生物活性和药理概况。尽管对空间位阻肽很感兴趣，但对在 α,α-二取代的 α-氨基酸和N之间带有酰胺键的肽的研究由于缺乏有效的合成方法，-烷基α-氨基酸仍未得到充分探索。在这里，我们描述了一种高产合成方法来获得氨基酸之间这种极度空间位阻的肽键。该反应发生在具有 α,α-二取代的 α-酰胺腈的肽和具有N-烷基半胱氨酸的第二肽之间，无需偶联剂。
• Design, synthesis and biological evaluation of peptide derivatives of l-dopa as anti-parkinsonian agents
  作者：Tao Zhou、Robert C. Hider、Peter Jenner、Bruce Campbell、Christopher J. Hobbs、Sarah Rose、Mark Jairaj、Kayhan A. Tayarani-Binazir、Alexander Syme

  DOI：10.1016/j.bmcl.2013.08.007

  日期：2013.10

  A series of dipeptide derivatives of L-dopa were synthesized and investigated for their pharmacological activity using the unilaterally 6-hydroxydopamine (6-OHDA)-lesioned rat as an experimental model of Parkinson's disease. Among them, (S)-isopropyl 2-(2-amino-2-methylpropanamido)-3-(3,4-dihydroxyphenyl) propanoate (4g) was found to be the most active compound, with 106% AUC activity and 149% peak activity of L-dopa after oral administration. (C) 2013 Elsevier Ltd. All rights reserved.
• 2, 4, 6-SUBSTITUTED PYRIDYL DERIVATIVE COMPOUNDS USEFUL AS BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP1740581B1

  公开（公告）日：2012-08-22
• US7968571B2
  申请人：——

  公开号：US7968571B2

  公开（公告）日：2011-06-28