3-Nonyloxyanilin | 55792-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-Nonyloxyanilin
• 英文别名: 3-(Nonyloxy)aniline；3-nonoxyaniline
• CAS: 55792-48-8
• 化学式: C₁₅H₂₅NO
• mdl: MFCD11197823
• 分子量: 235.37
• InChiKey: NHVYWXPUSZZRDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Nonyloxyanilin 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Ethyl 1-(2-methylpropyl)-7-nonoxy-4-oxoquinoline-3-carboxylate
  参考文献：
  名称：

  抗真菌环肽Rhopepteptin的新型拟肽：模拟物的合成及其抗真菌活性。

  摘要：

  [反应：请参见文字]。合成了新型的抗真菌环肽Rhodopeptin拟肽。与环状肽一样，发现所有三个杜鹃肽侧链的存在对于拟肽活性都是必不可少的。我们发现与母体化合物相比，新化合物表现出更大的抗真菌活性和改善的理化特性。

  DOI：

  10.1021/ol016394w
• 作为产物：
  描述：

  间硝基苯酚 在 镍 氢气 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 3-Nonyloxyanilin
  参考文献：
  名称：

  Walsh; Wooldridge; Jackson, European Journal of Medicinal Chemistry, 1977, vol. 12, # 6, p. 495 - 500

  摘要：

  DOI：

文献信息

• On the balance between syn- and anticlinicity in smectic phases formed by achiral hockey-stick mesogens with and without chiral dopants
  作者：Eva Enz、Sonja Findeisen-Tandel、Roman Dabrowski、Frank Giesselmann、Wolfgang Weissflog、Ute Baumeister、Jan Lagerwall

  DOI：10.1039/b820717h

  日期：——

  A series of achiral hockey-stick-shaped mesogens forming tilted smectic liquid crystal phases of synclinic SmC- as well as anticlinic SmCa-type was prepared and characterized. While all homologues exhibit both phases, the balance shifts from anticlinic to synclinic order upon elongation of the terminal chain at the meta- position, defining the hockey-stick shape. The elongation also leads to an increased kinetic hindrance of the transition between syn- and anticlinic phases and a decreased transition enthalpy. These observations indicate that a well-defined kink (short meta-substituted chain) promotes the anticlinic structure while a higher flexibility between kinked and rod-shape (long meta-substituted chain) promotes synclinic order. An intermediate chain-length homologue was selected as host material for doping with syn- and anticlinic rod-shaped chiral dopants, respectively, at varying concentrations. Opposite of what might be expected the balance between syn- and anticlinic order was not simply dictated by the choice of dopant. Instead, both types of tilting order prevailed with roughly the same strength as in the achiral host regardless of which chiral material was added, up to concentrations well beyond normal doping conditions. Thus, at least with hockey-stick-shaped achiral hosts, syn- as well as anticlinic chiral compounds can be used effectively as chiral dopants without necessarily having an important impact on the clinicity of the resulting mixture. The hockey-stick design concept should be useful in producing achiral anticlinic-forming mesogens for low-polarization, long-pitch antiferroelectric liquid crystal mixtures. Finally, we point out that a mixture study like the one carried out here yields a conclusive means of establishing the clinicity of achiral tilted smectics, an endeavour that can sometimes be far from trivial.

  制备并表征了一系列非手性曲棍球棒状介晶，形成向斜 SmC 型和背斜 SmCa 型倾斜近晶液晶相。虽然所有同系物都表现出两个相，但在间位末端链伸长时，平衡从背斜顺序转变为向斜顺序，从而定义了曲棍球棒形状。伸长还导致顺斜相和背斜相之间转变的动力学阻碍增加以及转变焓降低。这些观察结果表明，明确的扭结（短间位取代链）促进了背斜结构，而扭结和棒状（长间位取代链）之间更高的灵活性促进了向斜有序。选择中间链长同系物作为主体材料，分别以不同浓度掺杂顺斜棒状手性掺杂剂和背斜棒状手性掺杂剂。与预期相反，顺斜序和背斜序之间的平衡并不简单地由掺杂剂的选择决定。相反，无论添加哪种手性材料，两种类型的倾斜顺序都以与非手性主体大致相同的强度为主，浓度远远超出正常掺杂条件。因此，至少对于曲棍球棒形状的非手性主体，顺斜和反斜手性化合物可以有效地用作手性掺杂剂，而不必对所得混合物的临床性产生重要影响。曲棍球棒设计概念应该可用于生产低偏振、长螺距反铁电液晶混合物的非手性反斜形成介晶。最后，我们指出，像这里进行的混合研究提供了一种确定非手性倾斜近晶临床性的决定性方法，这一努力有时可能绝非微不足道。
• 5-Alkyloxytryptamines are membrane-targeting, broad-spectrum antibiotics
  作者：Katherine C. Faulkner、Katherine A. Hurley、Douglas B. Weibel

  DOI：10.1016/j.bmcl.2016.10.004

  日期：2016.11

  Antibiotic adjuvant therapy represents an exciting opportunity to enhance the activity of clinical antibiotics by co-dosing with a secondary small molecule. Successful adjuvants decrease the concentration of antibiotics used to defeat bacteria, increase activity (in some cases introducing activity against organisms that are drug resistant), and reduce the frequency at which drug-resistant bacteria emerge. We report that 5-alkyloxytryptamines are a new class of broad-spectrum antibacterial agents with exciting activity as antibiotic adjuvants. We synthesized 5-alkyloxytryptamine analogs and found that an alkyl chain length of 6-12 carbons and a primary ammonium group are necessary for the antibacterial activity of the compounds, and an alkyl chain length of 6-10 carbons increased the membrane permeability of Gram-positive and Gram-negative bacteria. Although several of the most potent analogs also have activity against the membranes of human embryonic kidney cells, we demonstrate that below the minimum inhibitory concentration (MIC) where mammalian cell toxicity is low these compounds may be successfully used as adjuvants for chloramphenicol, tetracycline, ciprofloxacin, and rifampicin against clinical strains of Salmonella typhimurium, Acinetobacter baumannii and Staphylococcus aureus, reducing MIC values by as much as several logs. (C) 2016 Elsevier Ltd. All rights reserved.
• ANTIMICROBIAL COMPOUNDS, COMPOSITIONS AND METHODS OF USE THEREOF
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US20160002163A1

  公开（公告）日：2016-01-07

  Described herein are antimicrobial compounds identified via a high-throughput screen to identify compounds that produce anucleate cells in E. coli after cell division occurs. Compound 1 (5-nonyloxytryptamine) and its analogs are small molecule inhibitors of the nucleoid occlusion system and/or proteins that are responsible for maintaining the structure of the chromosome. The antimicrobial compounds are useful to treat bacterial infections as well as to inhibit bacterial growth.
• US9440920B2
  申请人：——

  公开号：US9440920B2

  公开（公告）日：2016-09-13
• US9849099B2
  申请人：——

  公开号：US9849099B2

  公开（公告）日：2017-12-26