3-undecanyloxyaniline | 687974-93-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-undecanyloxyaniline
• 英文别名: 3-Undecyloxyanilin；3-Undecoxyaniline
• CAS: 687974-93-2
• 化学式: C₁₇H₂₉NO
• 分子量: 263.423
• InChiKey: MOSNYPKDBDAWML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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-undecanyloxyaniline 在 盐酸 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Lipophilicity-related inhibition of blood platelet aggregation by nipecotic acid anilides

  摘要：

  Using N-[4-(hexyloxy)phenyl]piperidine-3-carboxamide (17c) as a structural lead, a number of isomers, derivatives, and ring-opened analogs were synthesized and tested for their ability to block the in vitro aggregation of human platelets induced by adenosine 5'-diphosphate (ADP). For the most active compounds, inhibition of the platelet aggregation triggered by arachidonic acid (AA) and ADP-induced intraplatelet calcium mobilization was also demonstrated. Based on quantitative structure-activity relationships (QSARs), we proved the impact of hydrophobicity on antiplatelet activity by a nonlinear (parabolic or bilinear) relationship between pIC(50) and lipophilicity, as assessed by RP-HPLC capacity factors and Clog P (i.e. calculated 1-octanol-water partition coefficients). This study highlighted the following additional SARs: quasi-isolipophilic isomers of 17c (isonipecotanilides and pipecolinanilides) and ring-opened analogs (e.g. anilide of beta-alanine) exhibited lower antiplatelet activity; methylation of the piperidine nitrogen of 17c has no effect, whereas alkylation with an n-propyl group decreases the activity by a factor of approximately 2, most likely due to a conformation-dependent decrease in lipophilicity. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2004.03.003
• 作为产物：
  描述：

  1-溴十一烷 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 3-undecanyloxyaniline
  参考文献：
  名称：

  Synthesis and biological evaluation of novel N-(alkoxyphenyl)-aminocarbonylbenzoic acid derivatives as PTP1B inhibitors

  摘要：

  Based on the fact that petroselinic acid showed good inhibitory activity (IC50 = 6.99 mu mol/L) against protein tyrosine phophatase 1B(PTP1B) in vitro, a series of novel N-(alkoxyphenyl)-aminocarbonylbenzoic acid derivatives were designed and synthesized. The results indicated that most of the derivatives showed more potent activities against PTP1B. Especially, compound 13 had obvious activity with an IC50 of 106 nmol/L in vitro. (C) 2010 Song Wu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2010.07.005

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。
• Walsh; Wooldridge; Jackson, European Journal of Medicinal Chemistry, 1977, vol. 12, # 6, p. 495 - 500
  作者：Walsh、Wooldridge、Jackson、Gilmour

  DOI：——

  日期：——
• [EN] METHOD FOR PRODUCING LIQUID CRYSTAL DISPLAY ELEMENT<br/>[FR] PROCÉDÉ DE PRODUCTION D'UN ÉLÉMENT D'AFFICHAGE À CRISTAUX LIQUIDES<br/>[JA] 液晶表示素子の製造方法
  申请人：NISSAN CHEMICAL CORP

  公开号：WO2019163904A1

  公开（公告）日：2019-08-29

  非対称のチルト角発現能を維持しつつ、液晶セルの内部オフセット電圧が経時的に変化する現象を抑制できる液晶表示素子の提供。　第一の基板に、式（１）の構造を有する第一の液晶配向膜を形成する液晶配向膜形成工程と、第二の基板に、式（２－１）～（２－４）から選ばれる少なくとも１つの構造を有し、第一の液晶配向膜とは異なる組成である第二の液晶配向膜を形成する液晶配向膜形成工程と、その後、前記一対の基板の間に、液晶化合物を含む液晶層を形成する液晶層形成工程と、液晶セルに電圧を印加しながら紫外線を照射し、液晶層中の重合性化合物を反応させる工程と、を含むことを特徴とする液晶表示素子の製造方法。（式中の記号は、明細書に記載の通りである。）
• Synthesis and biological evaluation of novel N-(alkoxyphenyl)-aminocarbonylbenzoic acid derivatives as PTP1B inhibitors
  作者：Yuan Feng Tong、Pei Zhang、Feng Chen、Ling Hua Hao、Fei Ye、Jin Ying Tian、Song Wu

  DOI：10.1016/j.cclet.2010.07.005

  日期：2010.12

  Based on the fact that petroselinic acid showed good inhibitory activity (IC50 = 6.99 mu mol/L) against protein tyrosine phophatase 1B(PTP1B) in vitro, a series of novel N-(alkoxyphenyl)-aminocarbonylbenzoic acid derivatives were designed and synthesized. The results indicated that most of the derivatives showed more potent activities against PTP1B. Especially, compound 13 had obvious activity with an IC50 of 106 nmol/L in vitro. (C) 2010 Song Wu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Lipophilicity-related inhibition of blood platelet aggregation by nipecotic acid anilides
  作者：Agostino De Marco、Modesto de Candia、Andrea Carotti、Saverio Cellamare、Erica De Candia、Cosimo Altomare

  DOI：10.1016/j.ejps.2004.03.003

  日期：2004.6

  Using N-[4-(hexyloxy)phenyl]piperidine-3-carboxamide (17c) as a structural lead, a number of isomers, derivatives, and ring-opened analogs were synthesized and tested for their ability to block the in vitro aggregation of human platelets induced by adenosine 5'-diphosphate (ADP). For the most active compounds, inhibition of the platelet aggregation triggered by arachidonic acid (AA) and ADP-induced intraplatelet calcium mobilization was also demonstrated. Based on quantitative structure-activity relationships (QSARs), we proved the impact of hydrophobicity on antiplatelet activity by a nonlinear (parabolic or bilinear) relationship between pIC(50) and lipophilicity, as assessed by RP-HPLC capacity factors and Clog P (i.e. calculated 1-octanol-water partition coefficients). This study highlighted the following additional SARs: quasi-isolipophilic isomers of 17c (isonipecotanilides and pipecolinanilides) and ring-opened analogs (e.g. anilide of beta-alanine) exhibited lower antiplatelet activity; methylation of the piperidine nitrogen of 17c has no effect, whereas alkylation with an n-propyl group decreases the activity by a factor of approximately 2, most likely due to a conformation-dependent decrease in lipophilicity. (C) 2004 Elsevier B.V. All rights reserved.