7-Azabicyclo[2.2.1]heptane-2,7-dicarboxylic acid,7-(9H-fluoren-9-ylmethyl) 2-(phenylmethyl) ester, (1R,2R,4S)- | 918411-55-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 7-Azabicyclo[2.2.1]heptane-2,7-dicarboxylic acid,7-(9H-fluoren-9-ylmethyl) 2-(phenylmethyl) ester, (1R,2R,4S)-
• 英文别名: (1R,2R,4S)-7-azabicyclo[2.2.1]heptane-2,7-dicarboxylic acid 2-benzyl ester 7-(9H-fluoren-9-ylmethyl) ester
• CAS: 918411-55-9
• 化学式: C₂₉H₂₇NO₄
• 分子量: 453.538
• InChiKey: KWMALVKXMJUYLI-FBQMUFCQSA-N

物化性质

• 沸点：
  604.0±43.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.53
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7-Azabicyclo[2.2.1]heptane-2,7-dicarboxylic acid,7-(9H-fluoren-9-ylmethyl) 2-(phenylmethyl) ester, (1R,2R,4S)- 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以60%的产率得到(1R,2R,4S)-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
• 作为产物：
  描述：

  (1R,2R,4S)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester 在 sodium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 7-Azabicyclo[2.2.1]heptane-2,7-dicarboxylic acid,7-(9H-fluoren-9-ylmethyl) 2-(phenylmethyl) ester, (1R,2R,4S)-
  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