4-[5-(3-tert-butoxycarbonylamino-propoxy)-naphthalen-1-yloxy]-butyric acid tert-butyl ester | 309920-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[5-(3-tert-butoxycarbonylamino-propoxy)-naphthalen-1-yloxy]-butyric acid tert-butyl ester
• CAS: 309920-52-3
• 化学式: C₂₆H₃₇NO₆
• 分子量: 459.583
• InChiKey: UUSOKGQIQXLVRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  83.09
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-[5-(3-tert-butoxycarbonylamino-propoxy)-naphthalen-1-yloxy]-butyric acid tert-butyl ester 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 、 三乙胺 作用下， 以 三氟乙酸 、 水 、 乙腈 为溶剂， 反应 0.5h， 以80%的产率得到4-{5-[3-(9H-fluoren-9-ylmethoxycarbonylamino)-propoxy]-naphthalen-1-yloxy}-butyric acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and Conformational Characterization of Tethered, Self-Complexing 1,5-Dialkoxynaphthalene/1,4,5,8-Naphthalenetetracarboxylic Diimide Systems

  摘要：

  Chemists are beginning to explore the abiotic folding of synthetic chains, and the term "foldamers" has been used to characterize oligomers with a strong inclination to adopt specific, compact conformations. The characterization of folded structure in solution is one of the difficult challenges facing the foldamer Field. Aedamers were the first foldamers to make use of aromatic-aromatic interactions in water to direct folding and were designed to have several spectroscopic handles with which to probe folding conformations in solution. Herein is reported the synthesis and spectroscopic characterization of eleven aedamer dimers, with linkers chosen to provide a spectrum of lengths and flexibilities. The dimers, composed of one electron rich (1,5-dialkoxynaphthalene) and one electron deficient (1,4,5,8-naphthalenetetracarboxylic diimide) aromatic group tethered by a linker, are the smallest aedamer folding unit. The powerful spectroscopic handles associated with the stacked aedamer groups were exploited in a comprehensive spectroscopic analysis of conformation that included UV-vis absorption spectroscopy, fluorescence measurements (including time-resolved studies), as well as detailed NMR studies. The spectra were interpreted in the context of molecular modeling/spectral prediction and structural models were developed for the different dimers in aqueous solution. In most instances, the observed data was best described by an ensemble of predicted structures as opposed to one or few conformers. Thus, in the case of these aedamer dimers, "folding" does not appear to imply a two-state model with a rigid, unique conformation. Rather, the reported analysis indicates the data can best be described by a more dynamic model in which a given molecule spends its time in different folded conformations that are related by having a characteristic face-to-face stacking arrangement of the aromatic units.

  DOI：

  10.1021/ja0019225
• 作为产物：
  描述：

  N-Boc-3-氨基丙基溴 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 4-[5-(3-tert-butoxycarbonylamino-propoxy)-naphthalen-1-yloxy]-butyric acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and Conformational Characterization of Tethered, Self-Complexing 1,5-Dialkoxynaphthalene/1,4,5,8-Naphthalenetetracarboxylic Diimide Systems

  摘要：

  Chemists are beginning to explore the abiotic folding of synthetic chains, and the term "foldamers" has been used to characterize oligomers with a strong inclination to adopt specific, compact conformations. The characterization of folded structure in solution is one of the difficult challenges facing the foldamer Field. Aedamers were the first foldamers to make use of aromatic-aromatic interactions in water to direct folding and were designed to have several spectroscopic handles with which to probe folding conformations in solution. Herein is reported the synthesis and spectroscopic characterization of eleven aedamer dimers, with linkers chosen to provide a spectrum of lengths and flexibilities. The dimers, composed of one electron rich (1,5-dialkoxynaphthalene) and one electron deficient (1,4,5,8-naphthalenetetracarboxylic diimide) aromatic group tethered by a linker, are the smallest aedamer folding unit. The powerful spectroscopic handles associated with the stacked aedamer groups were exploited in a comprehensive spectroscopic analysis of conformation that included UV-vis absorption spectroscopy, fluorescence measurements (including time-resolved studies), as well as detailed NMR studies. The spectra were interpreted in the context of molecular modeling/spectral prediction and structural models were developed for the different dimers in aqueous solution. In most instances, the observed data was best described by an ensemble of predicted structures as opposed to one or few conformers. Thus, in the case of these aedamer dimers, "folding" does not appear to imply a two-state model with a rigid, unique conformation. Rather, the reported analysis indicates the data can best be described by a more dynamic model in which a given molecule spends its time in different folded conformations that are related by having a characteristic face-to-face stacking arrangement of the aromatic units.

  DOI：

  10.1021/ja0019225