2-tert-butoxycarbonylamino-3-phenoxycyclopentanecarboxylic acid | 476371-38-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-tert-butoxycarbonylamino-3-phenoxycyclopentanecarboxylic acid
• 英文别名: (1R,2S,3S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenoxycyclopentane-1-carboxylic acid
• CAS: 476371-38-7
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: KXWBLUSOESYREB-RDBSUJKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-tert-butoxycarbonylamino-3-phenoxycyclopentanecarboxylic acid 在 盐酸 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 生成 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenoxycyclopentanecarboxylic acid
  参考文献：
  名称：

  Stereoselective Synthesis of 3-Substituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation into Short 12-Helical β-Peptides That Fold in Water

  摘要：

  A stereoselective synthetic route is reported for the introduction of side chains at the 3-position of trans-2-aminocyclopentanecarboxylic acid (ACPC). Ring opening of the aziridine 2-benzyloxymethyl-6-azabicyclo[3.1.0]hexane with selected nucleophiles occurs in a regioselective manner and provides ACPC precursors with functional groups at the 3-position, trans to the 2-amino group. Oligomers composed of the 3-substituted ACPC residues maintain the 12-helical conformation displayed by the nonsubstituted analogues, as shown by their similar circular dichroism signatures. The added diversity of the new residues provides good dispersion of NMR signals, allowing the assignment of nearly all the NOE signals of a selected hexamer in aqueous solution. The NOES between protons on nonadjacent residues are characteristic of the 12-helix. 3-Substituted ACPC residues allow one to arrange specific functional groups in a geometrically defined fashion, which should facilitate the design of beta-peptides for biological applications.

  DOI：

  10.1021/ja0258778
• 作为产物：
  描述：

  [2-(benzyloxymethyl)-5-phenoxycyclopentyl]carbamic acid tert-butyl ester 在 10percent Pd/C jones reagent 、 甲酸铵 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 16.0h， 生成 2-tert-butoxycarbonylamino-3-phenoxycyclopentanecarboxylic acid
  参考文献：
  名称：

  Stereoselective Synthesis of 3-Substituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation into Short 12-Helical β-Peptides That Fold in Water

  摘要：

  A stereoselective synthetic route is reported for the introduction of side chains at the 3-position of trans-2-aminocyclopentanecarboxylic acid (ACPC). Ring opening of the aziridine 2-benzyloxymethyl-6-azabicyclo[3.1.0]hexane with selected nucleophiles occurs in a regioselective manner and provides ACPC precursors with functional groups at the 3-position, trans to the 2-amino group. Oligomers composed of the 3-substituted ACPC residues maintain the 12-helical conformation displayed by the nonsubstituted analogues, as shown by their similar circular dichroism signatures. The added diversity of the new residues provides good dispersion of NMR signals, allowing the assignment of nearly all the NOE signals of a selected hexamer in aqueous solution. The NOES between protons on nonadjacent residues are characteristic of the 12-helix. 3-Substituted ACPC residues allow one to arrange specific functional groups in a geometrically defined fashion, which should facilitate the design of beta-peptides for biological applications.

  DOI：

  10.1021/ja0258778

文献信息

• Stereoselective Synthesis of 3-Substituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation into Short 12-Helical β-Peptides That Fold in Water
  作者：Matthew G. Woll、John D. Fisk、Paul R. LePlae、Samuel H. Gellman

  DOI：10.1021/ja0258778

  日期：2002.10.1

  A stereoselective synthetic route is reported for the introduction of side chains at the 3-position of trans-2-aminocyclopentanecarboxylic acid (ACPC). Ring opening of the aziridine 2-benzyloxymethyl-6-azabicyclo[3.1.0]hexane with selected nucleophiles occurs in a regioselective manner and provides ACPC precursors with functional groups at the 3-position, trans to the 2-amino group. Oligomers composed of the 3-substituted ACPC residues maintain the 12-helical conformation displayed by the nonsubstituted analogues, as shown by their similar circular dichroism signatures. The added diversity of the new residues provides good dispersion of NMR signals, allowing the assignment of nearly all the NOE signals of a selected hexamer in aqueous solution. The NOES between protons on nonadjacent residues are characteristic of the 12-helix. 3-Substituted ACPC residues allow one to arrange specific functional groups in a geometrically defined fashion, which should facilitate the design of beta-peptides for biological applications.