4,7-Bis(2-methylpropoxy)-9-(phenylcarbamoyl)-1,10-phenanthroline-2-carboxylic acid | 877869-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 4,7-Bis(2-methylpropoxy)-9-(phenylcarbamoyl)-1,10-phenanthroline-2-carboxylic acid
• CAS: 877869-07-3
• 化学式: C₂₈H₂₉N₃O₅
• 分子量: 487.555
• InChiKey: OEIWFYFKQHZZST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,7-Bis(2-methylpropoxy)-9-(phenylcarbamoyl)-1,10-phenanthroline-2-carboxylic acid 在 氢氧化钾 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 53.0h， 生成 9-[C-hydroxy-N-[2-[[hydroxy-[9-(C-hydroxy-N-phenylcarbonimidoyl)-4,7-bis(2-methylpropoxy)-1,10-phenanthrolin-2-yl]methylidene]amino]phenyl]carbonimidoyl]-4,7-bis(2-methylpropoxy)-1,10-phenanthroline-2-carboxylic acid
  参考文献：
  名称：

  菲咯啉二甲酰胺基螺旋折叠剂：甲醇中稳定的螺旋结构。

  摘要：

  一系列新的芳族低聚酰胺2 - 5基于1,10-菲咯啉二酸和ö苯二胺必须通过一个会聚段耦合策略被合成。这些低聚物可以通过分子内的氢键和芳族堆积相互作用折叠成溶液中明确定义的螺旋结构，这一点已由11 H NMR，荧光和UV / vis光谱。特别地，发现与在氯仿和二氯甲烷中相比，低聚物在甲醇中更有利于折叠成稳定的螺旋结构。固态形成的螺旋形折叠剂已经通过单晶X射线衍射分析进行了表征。结果表明，钢绞线的高曲率导致2和21都绕了半圈，4绕了三圈，而5绕了近四圈。

  DOI：

  10.1021/jo052222r
• 作为产物：
  描述：

  methyl 4-isobutoxy-8-nitroquinoline-2-carboxylate 在 palladium on activated charcoal 氢氧化钾 、 氯化亚砜 、 偶氮二甲酸二异丙酯 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二苯醚 、 二氯甲烷 为溶剂， 反应 43.0h， 生成 4,7-Bis(2-methylpropoxy)-9-(phenylcarbamoyl)-1,10-phenanthroline-2-carboxylic acid
  参考文献：
  名称：

  菲咯啉二甲酰胺基螺旋折叠剂：甲醇中稳定的螺旋结构。

  摘要：

  一系列新的芳族低聚酰胺2 - 5基于1,10-菲咯啉二酸和ö苯二胺必须通过一个会聚段耦合策略被合成。这些低聚物可以通过分子内的氢键和芳族堆积相互作用折叠成溶液中明确定义的螺旋结构，这一点已由11 H NMR，荧光和UV / vis光谱。特别地，发现与在氯仿和二氯甲烷中相比，低聚物在甲醇中更有利于折叠成稳定的螺旋结构。固态形成的螺旋形折叠剂已经通过单晶X射线衍射分析进行了表征。结果表明，钢绞线的高曲率导致2和21都绕了半圈，4绕了三圈，而5绕了近四圈。

  DOI：

  10.1021/jo052222r

文献信息

• Conformationally constrained aromatic oligoamide foldamers with supersecondary structure motifs
  作者：Hai-Yu Hu、Jun-Feng Xiang、Chuan-Feng Chen

  DOI：10.1039/b903178b

  日期：——

  The design, synthesis, and structural studies of aromatic foldamers based on oligo(phenanthroline dicarboxamide)s that displayed supersecondary structure motifs have been described. Governed by a combined conformational restriction, the foldamers adopted well defined and compact 3D structures, which have been validated by UV/Vis, NMR spectra, and X-ray crystal analysis. The results presented here would offer a useful route for the de novo design of aromatic oligoamide foldamers with distinctive structural architectures.

  本研究介绍了基于寡（菲罗啉二甲酰胺）的芳香族折叠物的设计、合成和结构研究，这些折叠物显示了超二级结构主题。在组合构象限制的作用下，折叠器采用了定义明确、结构紧凑的三维结构，并通过紫外/可见光谱、核磁共振光谱和 X 射线晶体分析进行了验证。本文介绍的结果将为从头设计具有独特结构架构的芳香族低聚酰胺折叠体提供一条有用的途径。
• Chiral Induction in Phenanthroline-Derived Oligoamide Foldamers:  An Acid- and Base-Controllable Switch in Helical Molecular Strands
  作者：Hai-Yu Hu、Jun-Feng Xiang、Yong Yang、Chuan-Feng Chen

  DOI：10.1021/ol8001688

  日期：2008.3.1

  A series of phenanthroline-derived oligoamides bearing a chiral (R)-phenethylamino end group were synthesized that displayed chiral helical induction and subsequently formed one-hand helical foldamers in solution. Moreover, an acid- and base-controllable switch in the helical molecular strands was observed, which has been demonstrated by NMR, UV-vis, and circular dichroism spectroscopy.
• Folding-Induced Selective Hydrogenation of Helical 9,10-Anthraquinone Analogues
  作者：Hai-Yu Hu、Jun-Feng Xiang、Jing Cao、Chuan-Feng Chen

  DOI：10.1021/ol802241h

  日期：2008.11.6

  The first selective catalytic hydrogenation induced by the artificial helix based on oligo(phenanthroline dicarboxamide)s containing a 9,10-anthraquinone subunit is described. Due to the steric hindrance within the helically folded oligomers, the selective reductions of the anthraquinone units were completely different from those of model substrates, which subsequently mimicked the enzyme catalysis for preventing some reactions from occurring.
• A Helix−Turn−Helix Supersecondary Structure Based on Oligo(phenanthroline dicarboxamide)s
  作者：Hai-Yu Hu、Jun-Feng Xiang、Yong Yang、Chuan-Feng Chen

  DOI：10.1021/ol702720q

  日期：2008.1.1

  An artificial helix-turn-helix (HTH) supersecondary structure based on the oligo(phenanthroline dicarboxamide)s, in which the 2,2'-dimethoxy-1,1'-binaphthyl-6,6'-diamine subunit was utilized as the turn to impart a bias in the twist sense of the supersecondary structure, was reported. The HTH structure has been demonstrated by UV/vis, NMR, CD spectra, and X-ray crystal analysis.
• Probing the Dynamic Environment-Associated Conformational Conversion from Secondary to Supersecondary Structures in Oligo(phenanthroline dicarboxamide)s
  作者：Hai-Yu Hu、Wei Xue、Zhi-Qiang Hu、Jun-Feng Xiang、Chuan-Feng Chen、Sheng-Gui He

  DOI：10.1021/jo900647d

  日期：2009.7.17

  The special structural features of the oligo(phenanthroline dicarboxamide)s and their dynamic environment-associated conformational conversion from secondary helical structure to supersecondary helix-turn structure, owing to the conversion of the CONH bond from s-cis form to s-trans form, have been experimentally and theoretically characterized by X-ray crystallographic, variable-ternperature H-1 NMR, variable-ternperature circular dichroism techniques, and computational studies. It has been demonstrated that the solvent effects together with intramolecular hydrogen bonds and pi-pi stacking play a key role in stabilizing both the secondary and supersecondary structures. Furthermore, by introducing the intramolecular F center dot center dot center dot H-N hydrogen bond to restrict the rotation about the CONH-aryl bonds, the oligomers 6 and 7 have been synthesized, which showed well-defined and predictable secondary helical conformations in solution and in the solid state.