3-phenyl-2-{[2-(2,2,2-trifluoroacetylamino)acetyl]trimethylsilylmethylamino}propionic acid methyl ester | 429685-00-7

• 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: 3-phenyl-2-{[2-(2,2,2-trifluoroacetylamino)acetyl]trimethylsilylmethylamino}propionic acid methyl ester
• 英文别名: methyl (2S)-3-phenyl-2-[[2-[(2,2,2-trifluoroacetyl)amino]acetyl]-(trimethylsilylmethyl)amino]propanoate
• CAS: 429685-00-7
• 化学式: C₁₈H₂₅F₃N₂O₄Si
• 分子量: 418.488
• InChiKey: IRRKFPSRYGCFAV-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-phenyl-2-{[2-(2,2,2-trifluoroacetylamino)acetyl]trimethylsilylmethylamino}propionic acid methyl ester 在 三氟化硼乙醚 、 tetrabutylammonium tetrafluoroborate 作用下， 以 乙醚 为溶剂， 反应 17.0h， 生成 2-{but-3-enyl[2-(2,2,2-trifluoroacetylamino)acetyl]amino}-3-phenylpropionic acid methyl ester
  参考文献：
  名称：

  Building Functionalized Peptidomimetics:  Use of Electroauxiliaries for Introducing N-Acyliminium Ions into Peptides

  摘要：

  A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.

  DOI：

  10.1021/ja064737l
• 作为产物：
  描述：

  L-苯丙氨酸甲酯 在 五氯化磷 、 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-phenyl-2-{[2-(2,2,2-trifluoroacetylamino)acetyl]trimethylsilylmethylamino}propionic acid methyl ester
  参考文献：
  名称：

  甲硅烷基取代的氨基酸：构建选择性功能化拟肽的新途径。

  摘要：

  [反应：请参见文字]。甲硅烷基化的氨基酸已被掺入肽中，然后利用阳极氧化反应转化为N-酰基亚胺离子。结果是一种在肽内选择性掺入构象限制或外部亲核试剂的方法。

  DOI：

  10.1021/ol025776e

文献信息

• Building Functionalized Peptidomimetics:  Use of Electroauxiliaries for Introducing <i>N</i>-Acyliminium Ions into Peptides
  作者：Haizhou Sun、Connor Martin、David Kesselring、Rebecca Keller、Kevin D. Moeller

  DOI：10.1021/ja064737l

  日期：2006.10.1

  A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.
• Silyl-Substituted Amino Acids:  New Routes to the Construction of Selectively Functionalized Peptidomimetics
  作者：Haizhou Sun、Kevin D. Moeller

  DOI：10.1021/ol025776e

  日期：2002.5.1

  [reaction: see text]. Silylated amino acids have been incorporated into peptides and then converted into N-acyliminium ions with the use of an anodic oxidation reaction. The result is a method for selectively incorporating conformational constraints or external nucleophiles within the peptide.

  [反应：请参见文字]。甲硅烷基化的氨基酸已被掺入肽中，然后利用阳极氧化反应转化为N-酰基亚胺离子。结果是一种在肽内选择性掺入构象限制或外部亲核试剂的方法。