(1S,2S,4R)-7-azabicyclo[2.2.1]heptane-2,7-dicarboxylic acid 7-(9H-fluoren-9-ylmethyl) ester | 918411-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (1S,2S,4R)-7-azabicyclo[2.2.1]heptane-2,7-dicarboxylic acid 7-(9H-fluoren-9-ylmethyl) ester
• 英文别名: (1S,2S,4R)-7-(((9H-fluoren-9-yl)methoxy)carbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid；(1S,2S,4R)-7-(9H-fluoren-9-ylmethoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid
• CAS: 918411-64-0
• 化学式: C₂₂H₂₁NO₄
• 分子量: 363.413
• InChiKey: WFCSGQCVDZALMQ-MJWYBRSISA-N

物化性质

• 沸点：
  570.1±33.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R)-7-azabicyclo[2.2.1]heptane-2,7-dicarboxylic acid 7-(9H-fluoren-9-ylmethyl) ester 生成 (1S,2S,4R)-7-{(1S,2S,4R)-7-[(1S,2S,4R)-7-((1S,2S,4R)-7-Aza-bicyclo[2.2.1]heptane-2-carbonyl)-7-aza-bicyclo[2.2.1]heptane-2-carbonyl]-7-aza-bicyclo[2.2.1]heptane-2-carbonyl}-7-aza-bicyclo[2.2.1]heptane-2-carboxylic acid amide
  参考文献：
  名称：

  Oligomers of β-amino acid bearing non-planar amides form ordered structures

  摘要：

  In this report, we explore the feasibility of using bicyclic chiral beta-amino acids, (1R,2R,4S)- and (1S,2S,4R)-7-azabicyclo[2.2.1]-heptane-2-carboxylic acid (R-Ah2c and S-Ah2c, respectively), to prepare novel peptides with unique properties. Facile cis-trans isomerization of the non-planar amide bonds of these beta-amino acids should result in great flexibility of the backbone structure of beta-peptides containing them. Indeed, oligomers of these amino acids showed thermostability and characteristic CD absorptions, which were not concentration-dependent, suggesting that the oligomers remained monomeric. The results indicated the formation of self-organized monomeric structures with chain-length-dependent stabilization. Energy calculations suggested that the peptides can take helical structures in which the energy barriers to cis-trans isomerization are greater for the central amide bonds than for the terminal amides. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.062
• 作为产物：
  描述：

  (1S,2S,4R)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 、 sodium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (1S,2S,4R)-7-azabicyclo[2.2.1]heptane-2,7-dicarboxylic acid 7-(9H-fluoren-9-ylmethyl) ester
  参考文献：
  名称：

  Oligomers of β-amino acid bearing non-planar amides form ordered structures

  摘要：

  In this report, we explore the feasibility of using bicyclic chiral beta-amino acids, (1R,2R,4S)- and (1S,2S,4R)-7-azabicyclo[2.2.1]-heptane-2-carboxylic acid (R-Ah2c and S-Ah2c, respectively), to prepare novel peptides with unique properties. Facile cis-trans isomerization of the non-planar amide bonds of these beta-amino acids should result in great flexibility of the backbone structure of beta-peptides containing them. Indeed, oligomers of these amino acids showed thermostability and characteristic CD absorptions, which were not concentration-dependent, suggesting that the oligomers remained monomeric. The results indicated the formation of self-organized monomeric structures with chain-length-dependent stabilization. Energy calculations suggested that the peptides can take helical structures in which the energy barriers to cis-trans isomerization are greater for the central amide bonds than for the terminal amides. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.062