2-trimethylsilylethyl (2S)-1-[(2S,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylselanylbutanoyl]pyrrolidine-2-carboxylate | 190598-41-5

• 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: 2-trimethylsilylethyl (2S)-1-[(2S,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylselanylbutanoyl]pyrrolidine-2-carboxylate
• CAS: 190598-41-5
• 化学式: C₂₅H₄₀N₂O₅SeSi
• 分子量: 555.649
• InChiKey: PXWAUEKXECADCO-JBACZVJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-trimethylsilylethyl (2S)-1-[(2S,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylselanylbutanoyl]pyrrolidine-2-carboxylate 在 盐酸 、 四丁基氟化铵 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙腈 为溶剂， 生成 (S)-1-[(2S,3S)-3-((S)-2-Amino-propionylamino)-2-phenylselanyl-butyryl]-pyrrolidine-2-carboxylic acid ((S)-1-dimethylcarbamoyl-2-methyl-propyl)-amide
  参考文献：
  名称：

  Design of a novel secondary structure scaffolding device: Induction of a reverse turn in tetrapeptides by incorporating a β-amino acid and stereocontrolled free radical α-substitution reactions in peptide motifs

  摘要：

  The incorporation of alpha-substituted beta-amino acids into a tetrapeptide motif induces a reverse turn in aprotic solvent systems as revealed by NOESY and ROESY techniques, and by CD spectra. The conformations of these compounds have been studied by molecular modeling, and further supported by performing a highly stereoselective free radical allylation reaction on an alpha-phenylselena beta-amino acid unit within the tetrapeptide. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00612-6
• 作为产物：
  描述：

  (s)-3-boc-氨基丁酸甲酯 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 生成 2-trimethylsilylethyl (2S)-1-[(2S,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylselanylbutanoyl]pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Design of a novel secondary structure scaffolding device: Induction of a reverse turn in tetrapeptides by incorporating a β-amino acid and stereocontrolled free radical α-substitution reactions in peptide motifs

  摘要：

  The incorporation of alpha-substituted beta-amino acids into a tetrapeptide motif induces a reverse turn in aprotic solvent systems as revealed by NOESY and ROESY techniques, and by CD spectra. The conformations of these compounds have been studied by molecular modeling, and further supported by performing a highly stereoselective free radical allylation reaction on an alpha-phenylselena beta-amino acid unit within the tetrapeptide. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00612-6