(1S,2S,4R)-7-azabicyclo[2.2.1]heptane-2,7-dicarboxylic acid 2-benzyl ester 7-(9H-fluoren-9-ylmethyl) ester | 918411-58-2

• 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 2-benzyl ester 7-(9H-fluoren-9-ylmethyl) ester
• 英文别名: 2-O-benzyl 7-O-(9H-fluoren-9-ylmethyl) (1S,2S,4R)-7-azabicyclo[2.2.1]heptane-2,7-dicarboxylate
• CAS: 918411-58-2
• 化学式: C₂₉H₂₇NO₄
• 分子量: 453.538
• InChiKey: KWMALVKXMJUYLI-RAHIQWLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R)-7-azabicyclo[2.2.1]heptane-2,7-dicarboxylic acid 2-benzyl ester 7-(9H-fluoren-9-ylmethyl) ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成
  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)-2-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester 在 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium carbonate 、 N,N'-二环己基碳二亚胺 、 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 20.0h， 生成 (1S,2S,4R)-7-azabicyclo[2.2.1]heptane-2,7-dicarboxylic acid 2-benzyl ester 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

文献信息

• Oligomers of β-amino acid bearing non-planar amides form ordered structures
  作者：Yuko Otani、Shiroh Futaki、Tatsuto Kiwada、Yukio Sugiura、Atsuya Muranaka、Nagao Kobayashi、Masanobu Uchiyama、Kentaro Yamaguchi、Tomohiko Ohwada

  DOI：10.1016/j.tet.2006.09.062

  日期：2006.12

  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.