1-(9-bromononyloxy)-4-nitrobenzene | 134847-74-8

• 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: 1-(9-bromononyloxy)-4-nitrobenzene
• 英文别名: 1-(9-Bromononoxy)-4-nitrobenzene
• CAS: 134847-74-8
• 化学式: C₁₅H₂₂BrNO₃
• 分子量: 344.249
• InChiKey: BKFGIOBNKMUCQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(9-bromononyloxy)-4-nitrobenzene 、 苯胺 反应 1.5h， 以94%的产率得到N-[9-(4-nitrophenoxy)nonyl]aniline
  参考文献：
  名称：

  Bifunctional reactivity of the nitrophenoxyl group in intramolecular photoreactions

  摘要：

  The photochemical behavior of a homologous series of compounds, p-O2NC6H4O(CH2)(n)NHPh (n = 2-10, 12, and 16) in acetonitrile is reported. The lower (n = 2-6) homologues undergo an apparently nucleophilic type rearrangement to give omega-((p-nitrophenyl)amino)alkanol, while the higher homologues (n greater-than-or-equal-to 8) undergo an intramolecular photoredox reaction accompanied by C-N bond cleavage to give omega-(p-nitrosophenoxy)alkanal and aniline. The n = 7 homologue is situated at the switching point of these two reaction pathways, exhibiting neither type of photoreactions. Photoinduced intramolecular electron transfer to generate a radical ion pair is observed for all homologues, and the quantum yield decreases with increasing chain length. This species is the intermediate in the photorearrangement, for which the effect of base-catalysis is discussed in connection with the reaction mechanism. Comparison of the quantum yield for the electron transfer in 1 with that in 1-(anilinomethyl)-4-((p-nitrophenoxy)methyl)cyclohexane reveals the dominance of through-bond electron-transfer mechanism in the higher (n greater-than-or-equal-to 6) homologues. The reaction quantum yield vs chain length profile is discussed in terms of the relative quantum yield of the radical ion pair, the chain conformation, and the photoredox reaction mechanism.

  DOI：

  10.1021/jo00016a017
• 作为产物：
  描述：

  对硝基苯酚 、 1,9-二溴壬烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以43%的产率得到1-(9-bromononyloxy)-4-nitrobenzene
  参考文献：
  名称：

  Hybrid Ortho/Allosteric Ligands for the Adenosine A₁ Receptor

  摘要：

  Many G protein-coupled receptors (GPCRs), including the adenosine A(1) receptor (A(1)AR), have been shown to be allosterically modulated by small molecule ligands. So far, in the absence of structural information, the exact location of the allosteric site on the A(1)AR is not known. We synthesized a series of bivalent ligands (4) with an increasing linker length between the orthosteric and allosteric pharmacophores and used these as tools to search for the allosteric site on the A(1)AR. The compounds were tested in both equilibrium radioligand displacement and functional assays in the absence and presence of a reference allosteric enhancer, (2-amino-4,5-dimethy1-3-thienyl)-[3-(trifluoromethyl)phenyl]methanone, PD81,723 (1). Bivalent ligand N-6-[2-amino-3-(3,4-dichlorobenzoyl)-4,5,6,7-tetrahydrothieno[2,3-c]-pyridin-6-yl-9-nonyloxy-4-phenyl]-adenosine 4h (LUF6258) with a 9 carbon atom spacer did not show significant changes in affinity or potency in the presence of 1, indicating that this ligand bridged both sites on the receptor. Furthermore, 4h displayed an increase in efficacy, but not potency, compared to the parent, monovalent agonist 2. From molecular modeling studies, we speculate that the allosteric site of the A(1)AR is located in the proximity of the orthosteric site, possibly within the boundaries of the second extracellular loop of the receptor.

  DOI：

  10.1021/jm901252a

文献信息

• Liquid Crystalline Properties of 6-(4-Cyanobiphenyl-4’-yloxy)hexyl 4’-[ω-(<i>p</i>-Nitrophenyloxy)alkoxy]-4-biphenylcarboxylates
  作者：Toshio Itahara、Akihiro Nishino

  DOI：10.1080/15421406.2014.915662

  日期：2015.1.2

  A new series of liquid crystalline compounds, which contained two biphenyl and one p-nitrophenyl groups linked by two flexible spacers, were prepared. The flexible spacer between two biphenyl groups is fixed and consists of nine (odd number) atoms. The compounds showed nematic phase, although some of them exhibited nematic and smectic phases upon cooling. The isotropic-nematic transitional properties depended on the length and parity of the flexible spacers between the biphenyl and p-nitrophenyl groups. Such odd-even effect was in consistency with the feature of liquid crystal trimers. The liquid crystalline properties were compared with those of the related compounds.