1-(2-溴乙氧基)-4-[4-(2-溴乙氧基)苯基]苯 | 39800-60-7

• 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)-4-[4-(2-溴乙氧基)苯基]苯
• 英文名称: 4,4′-bis(2-bromoethoxy)-1,1′-biphenyl
• 英文别名: biphenyl-4,4'-di-(2-bromoethoxy)；4,4'-Bis-(2-bromaethoxy)-biphenyl；4,4'-Bis(2-bromoethoxy)-1,1'-biphenyl；1-(2-bromoethoxy)-4-[4-(2-bromoethoxy)phenyl]benzene
• CAS: 39800-60-7
• 化学式: C₁₆H₁₆Br₂O₂
• 分子量: 400.11
• InChiKey: ZEIGAFQNBKSLIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-溴乙氧基)-4-[4-(2-溴乙氧基)苯基]苯 在 三氟化硼乙醚 作用下， 以 甲醇 、 重水 、 1,2-二氯乙烷 为溶剂， 生成
  参考文献：
  名称：

  阳离子水溶性联苯[3]芳烃：超两亲物的合成，主宾复合和†

  摘要：

  合成了第一个阳离子水溶性联苯[3]芳烃，并研究了其与1-己烷磺酸钠的主客体络合作用，并将其进一步用于改变两亲性客体在水中的聚集。

  DOI：

  10.1039/c6ra18691b
• 作为产物：
  描述：

  4,4'-双(2-羟基乙氧基)联苯 在 溴 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以0.42 g的产率得到1-(2-溴乙氧基)-4-[4-(2-溴乙氧基)苯基]苯
  参考文献：
  名称：

  New Bis-thiazolium Analogues as Potential Antimalarial Agents: Design, Synthesis, and Biological Evaluation

  摘要：

  Bis-thiazolium salts are able to inhibit phosphatidylcholine biosynthesis in Plasmodium and to block parasite proliferation in the low nanomolar range. However, due to their physicochemical properties (i.e., permanent cationic charges, the flexibility, and lipophilic character of the alkyl chain), the oral bioavailability of these compounds is low. New series of bis-thiazolium-based drugs have been designed to overcome this drawback. They feature linker rigidification via the introduction of aromatic rings and/or a decrease in the overall lipophilicity through the introduction of heteroatoms. On the basis of the structure-activity relationships, a few of the promising compounds (9, 10, and 11) were found to exhibit potent antimalarial in vitro and in vivo activities (EC50 < 10 nM and ED50 ip < 0.7 mg/kg).

  DOI：

  10.1021/jm3014585

文献信息

• Macro Rings. V. Syntheses of Tetraoxaparacyclophanes Containing Two Biphenyl Nuclei
  作者：Joji Nishikido、Takahiko Inazu、Tamotsu Yoshino

  DOI：10.1246/bcsj.46.263

  日期：1973.1

  Three new tetraoxaparacyclophanes containing two biphenyl nuclei connected with oxypolymethyleneoxy bridges in the respective 4,4′-positions, such as 1,5,18,22-tetraoxa[5.0.5.0]paracyclophane I3, 1,6,19,24-tetraoxa-[6.0.6.0]paracyclophane I4, and 1,7,20,26-tetraoxa[7.0.7.0]paracyclophane I5, were synthesized. The UV, IR, and NMR spectra of these paracyclophanes were compared with those of the corresponding open-chain compound, IV3.

  合成了三种新的四氧亚环聚芳烃，这些化合物包含两个分别位于4,4'位的联苯核，通过氧聚甲烷氧桥连接，例如1,5,18,22-四氧[5.0.5.0]亚环聚芳烃I3、1,6,19,24-四氧[6.0.6.0]亚环聚芳烃I4和1,7,20,26-四氧[7.0.7.0]亚环聚芳烃I5。对这些亚环聚芳烃的紫外光、红外线和核磁共振谱与相应的开链化合物IV3进行了比较。
• An Efficient K₂CO₃-Promoted Synthesis of 1-Bromo-2-aryloxyethane Derivatives and Evaluation of Larval Mortality against<i> Aedes aegypti</i>
  作者：Yina Pájaro、Ángel Sathicq、Esneyder Puello-Polo、Astrid Pérez、Gustavo Romanelli、Jorge Trilleras

  DOI：10.1155/2017/6175315

  日期：——

  etherification of phenols to obtain 1-bromo-2-aryloxyethane derivatives were evaluated. The compounds were prepared by direct etherification of phenols with 1,2-dibromoethane using anhydrous K2CO3 and acetonitrile as solvent reaction, at 80°C, in a reaction time of 6 h. Under these conditions, excellent yields (71%–94%) were obtained, with low yields of secondary products. The anhydrous K2CO3 was recycled

  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%。
• Zuev, Russian Journal of General Chemistry, 1997, vol. 67, # 11, p. 1791 - 1793
  作者：Zuev

  DOI：——

  日期：——
• New Bis-thiazolium Analogues as Potential Antimalarial Agents: Design, Synthesis, and Biological Evaluation
  作者：Sergio A. Caldarelli、Siham El Fangour、Sharon Wein、Christophe Tran van Ba、Christian Périgaud、Alain Pellet、Henri J. Vial、Suzanne Peyrottes

  DOI：10.1021/jm3014585

  日期：2013.1.24

  Bis-thiazolium salts are able to inhibit phosphatidylcholine biosynthesis in Plasmodium and to block parasite proliferation in the low nanomolar range. However, due to their physicochemical properties (i.e., permanent cationic charges, the flexibility, and lipophilic character of the alkyl chain), the oral bioavailability of these compounds is low. New series of bis-thiazolium-based drugs have been designed to overcome this drawback. They feature linker rigidification via the introduction of aromatic rings and/or a decrease in the overall lipophilicity through the introduction of heteroatoms. On the basis of the structure-activity relationships, a few of the promising compounds (9, 10, and 11) were found to exhibit potent antimalarial in vitro and in vivo activities (EC50 < 10 nM and ED50 ip < 0.7 mg/kg).
• A cationic water-soluble biphen[3]arene: synthesis, host–guest complexation and fabrication of a supra-amphiphile
  作者：Jiong Zhou、Jie Yang、Zhihua Zhang、Guocan Yu

  DOI：10.1039/c6ra18691b

  日期：——

  The first cationic water-soluble biphen[3]arene was synthesized and its host–guest complexation with sodium 1-hexanesulfonate was investigated, which was further used to change the aggregation of the amphiphilic guest in water.

  合成了第一个阳离子水溶性联苯[3]芳烃，并研究了其与1-己烷磺酸钠的主客体络合作用，并将其进一步用于改变两亲性客体在水中的聚集。