(1S,2S,4R)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid | 918411-46-8

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1S,2S,4R)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid
• 英文别名: (1S,2S,4R)-7-(tert-Butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid；(1S,2S,4R)-7-[(2-methylpropan-2-yl)oxycarbonyl]-7-azabicyclo[2.2.1]heptane-2-carboxylic acid
• CAS: 918411-46-8
• 化学式: C₁₂H₁₉NO₄
• 分子量: 241.287
• InChiKey: XRDRXGVDCVQVPV-VGMNWLOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid 在 4-二甲氨基吡啶 、 sodium carbonate 、 N,N'-二环己基碳二亚胺 、 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 19.0h， 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
• 作为产物：
  描述：

  (+/-)-methyl endo-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylate 在 lithium hydroxide 、 草酰氯 、 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成 (1S,2S,4R)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid
  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.