Methyl 2-[6-(phenylmethoxycarbonylamino)hexylamino]acetate | 143192-27-2

• 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: Methyl 2-[6-(phenylmethoxycarbonylamino)hexylamino]acetate
• CAS: 143192-27-2
• 化学式: C₁₇H₂₆N₂O₄
• 分子量: 322.404
• InChiKey: YBKXNABJIFKSTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  BOC-L-苯丙氨酸 、 Methyl 2-[6-(phenylmethoxycarbonylamino)hexylamino]acetate 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 生成 methyl 2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]-[6-(phenylmethoxycarbonylamino)hexyl]amino]acetate
  参考文献：
  名称：

  Building units for N-backbone cyclic peptides. 1. Synthesis of protected N-(.omega.-aminoalkylene)amino acids and their incorporation into dipeptide units

  摘要：

  A variety of new amino acids which contain an omega-aminoalkylene group on the N(alpha)-amino nitrogen were synthesized by alkylation of alkylenediamines with alpha-halogeno acids. The reaction proceeds with inversion of configuration; thus, optically pure products were obtained when optically active a-halogeno acids were used. The N-(omega-aminoalkylene)amino acids were protected by orthogonal protecting groups to allow their incorporation into dipeptides by the "solution" techniques and into peptides by the solid-phase peptide synthesis (SPPS) methodology. A series of dipeptide analogs of Phe-Gly, Leu-Gly, Trp-Gly, Phe-Leu, and Phe-Ala in which the nitrogen of the peptide bond is alkylated by omega-aminoalkylene chains with various lengths were prepared. These new protected N-(omega-aminoalkylene)amino acids and their derived dipeptide units may be used as building blocks for conformationally constrained N-backbone cyclic peptides.

  DOI：

  10.1021/jo00047a022
• 作为产物：
  描述：

  ζ-aminohexylglycine 在 盐酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 25.0h， 生成 Methyl 2-[6-(phenylmethoxycarbonylamino)hexylamino]acetate
  参考文献：
  名称：

  Building units for N-backbone cyclic peptides. 1. Synthesis of protected N-(.omega.-aminoalkylene)amino acids and their incorporation into dipeptide units

  摘要：

  A variety of new amino acids which contain an omega-aminoalkylene group on the N(alpha)-amino nitrogen were synthesized by alkylation of alkylenediamines with alpha-halogeno acids. The reaction proceeds with inversion of configuration; thus, optically pure products were obtained when optically active a-halogeno acids were used. The N-(omega-aminoalkylene)amino acids were protected by orthogonal protecting groups to allow their incorporation into dipeptides by the "solution" techniques and into peptides by the solid-phase peptide synthesis (SPPS) methodology. A series of dipeptide analogs of Phe-Gly, Leu-Gly, Trp-Gly, Phe-Leu, and Phe-Ala in which the nitrogen of the peptide bond is alkylated by omega-aminoalkylene chains with various lengths were prepared. These new protected N-(omega-aminoalkylene)amino acids and their derived dipeptide units may be used as building blocks for conformationally constrained N-backbone cyclic peptides.

  DOI：

  10.1021/jo00047a022

文献信息

• Building units for N-backbone cyclic peptides. 1. Synthesis of protected N-(.omega.-aminoalkylene)amino acids and their incorporation into dipeptide units
  作者：Gerardo Byk、Chaim Gilon

  DOI：10.1021/jo00047a022

  日期：1992.10

  A variety of new amino acids which contain an omega-aminoalkylene group on the N(alpha)-amino nitrogen were synthesized by alkylation of alkylenediamines with alpha-halogeno acids. The reaction proceeds with inversion of configuration; thus, optically pure products were obtained when optically active a-halogeno acids were used. The N-(omega-aminoalkylene)amino acids were protected by orthogonal protecting groups to allow their incorporation into dipeptides by the "solution" techniques and into peptides by the solid-phase peptide synthesis (SPPS) methodology. A series of dipeptide analogs of Phe-Gly, Leu-Gly, Trp-Gly, Phe-Leu, and Phe-Ala in which the nitrogen of the peptide bond is alkylated by omega-aminoalkylene chains with various lengths were prepared. These new protected N-(omega-aminoalkylene)amino acids and their derived dipeptide units may be used as building blocks for conformationally constrained N-backbone cyclic peptides.