5-N-(11-azidoundecyl)-1-N,3-N-bis[(3S)-3,7-dimethyloctyl]benzene-1,3,5-tricarboxamide | 1416620-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-N-(11-azidoundecyl)-1-N,3-N-bis[(3S)-3,7-dimethyloctyl]benzene-1,3,5-tricarboxamide
• CAS: 1416620-39-7
• 化学式: C₄₀H₇₀N₆O₃
• 分子量: 683.034
• InChiKey: SCBOLOLMRBJQFV-HEVIKAOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  49
• 可旋转键数：
  29
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 二(对硝基苯基)叠氮膦酸酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以72%的产率得到5-N-(11-azidoundecyl)-1-N,3-N-bis[(3S)-3,7-dimethyloctyl]benzene-1,3,5-tricarboxamide
  参考文献：
  名称：

  Orthogonal Self-Assembly in Folding Block Copolymers

  摘要：

  We herein report the synthesis and characterization of ABA triblock copolymers that contain two complementary association motifs and fold into single-chain polymeric nanoparticles (SCPNs) via orthogonal self-assembly. The copolymers were prepared using atom-transfer radical polymerization (ATRP) and possess different pendant functional groups in the A and B blocks (alcohols in the A block and acetylenes in the B block). After postfunctionalization, the A block contains o-nitrobenzyl-protected 2-ureidopyrimidinone (UPy) moieties and the B block benzene-1,3,5-tricarboxamide (BTA) moieties. While the protected UPy groups dimerize after photoinduced deprotection of the o-nitrobenzyl group, the BTA moieties self-assemble into helical aggregates when temperature is reduced. In a two-step thermal/photoirradiation treatment under dilute conditions, the ABA block copolymer forms both BTA-based helical aggregates and UPy dimers intramolecularly. The sequential association of the two self-assembling motifs results in single-chain folding of the polymer, affording nanometer-sized particles with a compartmentalized interior. Variable-temperature NMR studies showed that the BTA and UPy self-assembly steps take place orthogonally (i.e., without mutual interference) in dilute solution. In addition, monitoring of the intramolecular self-assembly of BTA moieties into helical aggregates by circular dichroism spectroscopy showed that the stability of the aggregates is almost independent of UPy dimerization. Size-exclusion chromatography (SEC) and small-angle X-ray scattering analysis provided evidence of significant reductions in the hydrodynamic volume and radius of gyration, respectively, after photoinduced deprotection of the UPy groups; a 30-60% reduction in the size of the polymer chains was observed using SEC in CHCl3. Molecular imaging by atomic force microscopy (AFM) corroborated significant contraction of individual polymer chains due to intramolecular association of the BTA and UPy groups. The stepwise folding process resulting from orthogonal self-assembly-induced supramolecular interactions yields compartmentalized SCPNs comprised of distinct microdomains that mimick two secondary-structuring elements in proteins.

  DOI：

  10.1021/ja310422w