(S)-N-{3-[5-(3-Carboxy-propoxy)-naphthalen-1-yloxy]-propyl}-3-(9H-fluoren-9-ylmethoxycarbonylamino)-succinamic acid tert-butyl ester | 199126-09-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-N-{3-[5-(3-Carboxy-propoxy)-naphthalen-1-yloxy]-propyl}-3-(9H-fluoren-9-ylmethoxycarbonylamino)-succinamic acid tert-butyl ester
• CAS: 199126-09-5
• 化学式: C₄₀H₄₄N₂O₉
• 分子量: 696.797
• InChiKey: VPYUJZJHJWBPDV-XIFFEERXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  51.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  149.49
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-N-{3-[5-(3-Carboxy-propoxy)-naphthalen-1-yloxy]-propyl}-3-(9H-fluoren-9-ylmethoxycarbonylamino)-succinamic acid tert-butyl ester 、 乙酸酐 、 alkaline earth salt of/the/ methylsulfuric acid 以58%的产率得到(3S)-4-[3-[5-[4-[(2S)-3-carboxy-1-[3-[5-[4-[(2S)-3-carboxy-1-[3-[5-[4-[(2S)-3-carboxy-1-[3-[5-[4-(carboxymethylimino)-4-hydroxybutoxy]naphthalen-1-yl]oxypropylimino]-1-hydroxypropan-2-yl]imino-4-hydroxybutoxy]naphthalen-1-yl]oxypropylimino]-1-hydroxypropan-2-yl]imino-4-hydroxybutoxy]naphthalen-1-yl]oxypropylimino]-1-hydroxypropan-2-yl]imino-4-hydroxybutoxy]naphthalen-1-yl]oxypropylimino]-4-hydroxy-3-(1-hydroxyethylideneamino)butanoic acid
  参考文献：
  名称：

  Aromatic Oligomers that Form Hetero Duplexes in Aqueous Solution

  摘要：

  The electron-deficient 1,4,5,8-naphthalenetetracarboxylic diimide (Ndi) and electron-rich 1,5-dialkoxynaphthalene (Dan) have been shown to complex strongly with each other in water due to the hydrophobic effect as modulated through the electrostatic complementarity of the stacked dimer. Previously, oligomers of alternating Ndi and Dan units, termed aedamers, were the first foldamers to employ intramolecular aromatic stacking to effect the formation of secondary structure of nonnatural chains in aqueous solution. Described here is the use of this aromatic-aromatic (or pi-pi) interaction, this time in an intermolecular format, to demonstrate the self-assembly of stable hetero duplexes from a set of molecular strands (1a-4a) and (1b-4b) incorporating Ndi and Dan units, respectively. A 1-to-1 binding stoichiometry was determined from NMR and isothermal titration calorimetry (ITC) investigations, and these experiments indicated that association is enthalpically favored with the tetra-Ndi (4a) and tetra-Dan (4b) strands forming hetero duplexes (4a:4b) with a stability constant of 350 000 M-1 at T = 318 K. Polyacrylamide gel electrophoresis (PAGE) also illustrated the strong interaction between 4a and 4b and support a 1-to-1 binding mode even when one component is in slight excess. Overall, this system is the first to utilize complementary aromatic units to drive discrete self-assembly in aqueous solution. This new approach for designing assemblies is encouraging for future development of duplex systems with highly programmable modes of binding in solution or on surfaces.

  DOI：

  10.1021/ja0275358
• 作为产物：
  描述：

  [3-(5-hydroxy-naphthalen-1-yloxy)-propyl]-carbamic acid tert-butyl ester 在 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 、 potassium carbonate 作用下， 以 正庚烷 、 乙腈 、 三氟乙酸 为溶剂， 反应 29.0h， 生成 (S)-N-{3-[5-(3-Carboxy-propoxy)-naphthalen-1-yloxy]-propyl}-3-(9H-fluoren-9-ylmethoxycarbonylamino)-succinamic 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