1-(2-溴乙氧基)-2-苯基苯 | 3245-43-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2-溴乙氧基)-2-苯基苯
• 英文名称: 1-(2-bromoethoxy)-2-phenylbenzene
• 英文别名: 2-(2-bromoethoxy)-1,1'-biphenyl
• CAS: 3245-43-0
• 化学式: C₁₄H₁₃BrO
• 分子量: 277.161
• InChiKey: UQBMYWHWFZRRIL-UHFFFAOYSA-N

物化性质

• 熔点：
  66.5 °C
• 沸点：
  170-175 °C(Press: 5 Torr)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-溴乙氧基)-2-苯基苯 在 氨 、 苯 作用下， 生成 2-biphenyl-2-yloxy-ethylamine
  参考文献：
  名称：

  GB521575

  摘要：

  公开号：
• 作为产物：
  描述：

  1,2-二溴乙烷 、 邻苯基苯酚 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以85%的产率得到1-(2-溴乙氧基)-2-苯基苯
  参考文献：
  名称：

  K2CO3 促进的 1-Bromo-2-aryloxyethane 衍生物的有效合成和对埃及伊蚊幼虫死亡率的评估

  摘要：

  评价了反应参数对酚醚化得到1-溴-2-芳氧基乙烷衍生物的影响。该化合物是通过苯酚与 1,2-二溴乙烷的直接醚化反应制备的，使用无水碳酸钾和乙腈作为溶剂反应，在 80°C，反应时间为 6 小时。在这些条件下，获得了极好的收率（71%–94%），但副产品收率很低。无水碳酸钾通过简单过滤回收，真空干燥，重复使用。这些化合物通过常规光谱数据（MS 和 NMR）进行表征。杀幼虫活性结果表明，暴露于化合物 1-(2-溴乙氧基)-2-苯基苯 24 小时后，幼虫死亡率为 100%。

  DOI：

  10.1155/2017/6175315

文献信息

• Arylsulfonamide derivatives of (aryloxy)ethylpiperidines as selective 5-HT₇ receptor antagonists and their psychotropic properties
  作者：Paweł Zajdel、Vittorio Canale、Anna Partyka、Krzysztof Marciniec、Rafał Kurczab、Grzegorz Satała、Agata Siwek、Magdalena Jastrzębska-Więsek、Anna Wesołowska、Tomasz Kos、Piotr Popik、Andrzej J. Bojarski

  DOI：10.1039/c5md00166h

  日期：——

  A novel series of potent 5-HT₇ receptor antagonist and their antidepressant, anxiolytic and pro-cognitive properties is described.

  描述了一系列有效的5-HT₇受体拮抗剂及其抗抑郁、抗焦虑和促进认知的特性。
• Quinolinesulfonamides of Aryloxy-/Arylthio-ethyl Piperidines: Influence of an Arylether Fragment on 5-HT_1A/5-HT₇Receptor Selectivity
  作者：Katarzyna Grychowska、Krzysztof Marciniec、Vittorio Canale、Michał Szymiec、Grzegorz Glanowski、Grzegorz Satała、Andrzej Maślankiewicz、Maciej Pawłowski、Andrzej J. Bojarski、Paweł Zajdel

  DOI：10.1002/ardp.201200322

  日期：2013.3

  The solid‐phase synthesis of a new series of 19 biomimetics of long‐chain arylpiperazines, namely flexible quinoline sulfonamides of aryl(heteroaryl)oxy‐/heteroarylthio‐ethyl 4‐aminomethylpiperidines, is reported. Various structural modifications applied followed by biological evaluation for 5‐HT1A, 5‐HT6, and 5‐HT7 receptors gave further support of a possible replacement of arylpiperazine with ar

  报道了 19 种长链芳基哌嗪仿生物的固相合成，即芳基（杂芳基）氧基-/杂芳硫基-乙基 4-氨基甲基哌啶的柔性喹啉磺酰胺。应用各种结构修饰，随后对 5-HT1A、5-HT6 和 5-HT7 受体进行生物学评估，进一步支持了用脂环胺的芳氧基-/芳硫基-乙基衍生物替代芳基哌嗪的可能性，并在多样化后控制受体选择性芳基（杂芳基）氧基-/杂芳硫基-乙基片段。
• The multiobjective based design, synthesis and evaluation of the arylsulfonamide/amide derivatives of aryloxyethyl- and arylthioethyl- piperidines and pyrrolidines as a novel class of potent 5-HT7 receptor antagonists
  作者：Paweł Zajdel、Rafał Kurczab、Katarzyna Grychowska、Grzegorz Satała、Maciej Pawłowski、Andrzej J. Bojarski

  DOI：10.1016/j.ejmech.2012.07.043

  日期：2012.10

  An analysis of the virtual combinatorial library was used for refining a pilot set of 34 derivatives and designing a targeted 38-member library of the arylamide and arylsulfonamide derivatives of aryloxyethyl- and arylthioethyl-piperidines and pyrrolidines. All compounds 24-95 were synthesized according to an elaborated parallel solid-phase method and were biologically evaluated for their affinity for 5-HT7R. Additionally, the targeted library members were tested for 5-HT1A, 5-HT6, and D-2 receptors. Selected compounds of particular interest were examined for their intrinsic activity at 5-HT7R in vitro employing a cAMP assay. The study allowed us to identify compound 68 (4-fluoro-N-(1-2-[(propan-2-yl)phenoxylethyl}piperidin-4-yl) benzenesulfonamide) as a potent 5-HT7R ligand (K-i = 0.3 nM) with strong antagonistic properties (K-b = 1 nM) and a 1450-fold selectivity over 5-HT(1A)Rs. (C) 2012 Elsevier Masson SAS. All rights reserved.
• New Serotonin 5-HT_1A Receptor Agonists Endowed with Antinociceptive Activity <i>in Vivo</i>
  作者：Margarita Valhondo、Isabel Marco、Mar Martín-Fontecha、Henar Vázquez-Villa、José A. Ramos、Reinhard Berkels、Thomas Lauterbach、Bellinda Benhamú、María L. López-Rodríguez

  DOI：10.1021/jm400766k

  日期：2013.10.24

  We report the synthesis of new compounds 4-35 based on two different openings (A and B) of the chromane ring present in the previously identified 5-HT1A receptor (5-HT1AR) ligand 3. The synthesized compounds were assessed for binding affinity, selectivity, and functional activity at the 5-HT1AR Selected candidates resulting from B opening were also evaluated for their potential antinociceptive effect in vivo and pharmacokinetic properties in vitro. Analogue 19 [2-(4-[2-(2-ethoxyphenoxy)ethyl]amino}butyl)tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione] has been characterized as a high-affinity and potent 5-HT1AR agonist (K-i = 2.3 nM; EC50 = 19 nM). Pharmacokinetic studies indicated that compound 19 displays a good metabolic stability in human liver microsomes (t(1/2) similar to 3 h and CLint = 3.5 mL/min/kg, at 5 mu M), and a low level of protein binding (25%, at 5 mu M). Interestingly, 19 (3 mg/kg, ip, and 30 mg/kg, po) caused significant attenuation of formalin-induced behavior in early and late phases of the mouse intradermal formalin test of pain, and this in vivo effect was reversed by the selective 5-HT1AR antagonist WAY-100635. Thus, the new 5-HT1AR agonist identified in this work, 19, exhibits oral analgesic activity, and the results herein represent a step toward identifying new therapeutics for the control of pain.
• Some Cardiovascular Effects of a Series of Aryloxyalkylamines. I
  作者：J. Augstein、W. C. Austin、R. J. Boscott、S. M. Green、C. R. Worthing

  DOI：10.1021/jm00327a017

  日期：1965.5