1-[(6-bromohexyl)oxy]-4-fluorobenzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[(6-bromohexyl)oxy]-4-fluorobenzene
• 英文别名: 4-fluoro-1-(6-bromohexyloxy)benzene；1-(6-Bromohexoxy)-4-fluorobenzene
• 化学式: C₁₂H₁₆BrFO
• 分子量: 275.161
• InChiKey: YESKJRCPUIDQHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-吡啶-4-咪唑啉-2-酮 、 1-[(6-bromohexyl)oxy]-4-fluorobenzene 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以90%的产率得到1-[6-(4-Fluoro-phenoxy)-hexyl]-3-pyridin-4-yl-imidazolidin-2-one
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationship of Pyridyl Imidazolidinones:  A Novel Class of Potent and Selective Human Enterovirus 71 Inhibitors

  摘要：

  When skeletons of Win compounds were used as templates, computer-assisted drug design led to the identification of a novel series of imidazolidinone derivatives with significant antiviral activity against enterovirus 71(EV 71), the infection of which had resulted in about 80 fatalities during the 1998 epidemic outbreak in Taiwan. In addition to inhibiting all the genotypes (A, B, and C) of EV 71 in the submicromolar to low micromolar range, compounds 1 and 8 were extensively evaluated against a variety of viruses, showing potent activity against coxsackievirus A9 (IC50 = 0.47-0.55 muM) and coxsackievirus A24 (IC50 = 0.47-0.55 muM) as well as moderate activity against enterovirus 68 (IC50 = 2.13 muM) and echovirus 9 (IC50 = 2.6 muM). Our SAR studies revealed that imidazolidinone analogues with an aryl substituent at the para position of the phenoxyl ring, such as compounds 20, 21, 27, 57, 58, and 61, in general exhibited the highest activity against EV 71. Among them, compound 20 and its corresponding hydrochloride salt 57, in terms of potency and selectivity index, appear to be the most promising candidates in this series for further development of anti-EV-71 agents. Preliminary results of the study on the mode of action by a time-course experiment suggest that test compounds 1 and 8 can effectively inhibit the virus replication at the early stages, referring to virus attachment or uncoating. This indicates that the surface protein may be the target for this type of compounds.

  DOI：

  10.1021/jm010536a
• 作为产物：
  描述：

  5-溴-1-戊烯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 potassium carbonate 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 18.0h， 生成 1-[(6-bromohexyl)oxy]-4-fluorobenzene
  参考文献：
  名称：

  平衡烯丙基叠氮化物的选择性硼氢化

  摘要：

  据报道，平衡的烯丙基叠氮化物的铱( I ) 催化硼氢化仅以良好的收率和良好的官能团耐受性提供了烷-1-烯异构体的反马尔科夫尼科夫产物。

  DOI：

  10.1039/d1cc02520a

文献信息

• Iron-Catalyzed Cross-Coupling of Alkenyl Acetates
  作者：Dominik Gärtner、André Luiz Stein、Sabine Grupe、Johannes Arp、Axel Jacobi von Wangelin

  DOI：10.1002/anie.201504524

  日期：2015.9.1

  unreactive in cross‐coupling reactions which mostly employ more electrophilic halides or activated esters (triflates, tosylates). Acetates are cheap and easily accessible electrophiles but have not been used in cross‐couplings because the strong CO bond and high propensity to engage in unwanted acetylation and deprotonation. Reported herein is a selective iron‐catalyzed cross‐coupling of diverse alkenyl

  稳定的CO键通常在交叉偶联反应中没有反应性，而交叉偶联反应通常使用更多的亲电子卤化物或活化的酯（三氟甲磺酸酯，甲苯磺酸酯）。乙酸盐价格便宜，易于获得亲电试剂，但由于其强大的CO键和极高的参与不希望的乙酰化和去质子化的能力，因此并未用于交叉偶联中。本文报道了多种乙酸烯基酯的选择性铁催化交叉偶联，它在温和的反应条件下（0°C，2 h）与不含配体的催化剂（1-2 mol％）一起运行。
• Imidazolidinone compounds
  申请人：——

  公开号：US20030087936A1

  公开（公告）日：2003-05-08

  A compound having the formula: 1 in which R 1 , R 2 , R 3 , T, W, m, x, and y are defined as in the specification. Also disclosed is a method of treating enterovirus infection by using a compound described above.

  一个具有以下式子的化合物：1，其中R1、R2、R3、T、W、m、x和y的定义如规范中所述。还公开了一种利用上述化合物治疗肠道病毒感染的方法。
• Mild olefin formation <i>via</i> bio-inspired vitamin B₁₂ photocatalysis
  作者：Radha Bam、Alexandros S. Pollatos、Austin J. Moser、Julian G. West

  DOI：10.1039/d0sc05925k

  日期：——

  Herein we report a light-driven B12-based catalytic system that leverages this reactivity to convert alkyl electrophiles to olefins under incredibly mild conditions using only earth abundant elements. Further, this process exhibits a high level of regioselectivity, producing terminal olefins in moderate to excellent yield and exceptional selectivity. Finally, we are able to access a hitherto-unknown

  脱卤化氢或消除卤化氢等价物仍然是安装生物学上重要的烯烃官能团的最简单方法之一。然而，这种转化通常需要苛刻的强碱性条件、稀有贵金属或两者兼而有之，限制了其在复杂分子合成中的适用性。Nature 在新型维生素 B 12依赖性光感受器 CarH 中寻求一种补充方法，其中钴-碳键的光解导致在温和的生理相关条件下选择性形成烯烃。在这里，我们报告了一个光驱动的 B 12基于催化系统，利用这种反应性在极其温和的条件下仅使用地球丰富的元素将烷基亲电子试剂转化为烯烃。此外，该工艺表现出高水平的区域选择性，以中等至优异的收率和出色的选择性生产末端烯烃。最后，我们能够使用两种钴催化剂串联使用迄今为止未知的转化，远程消除来生产具有优异区域选择性的亚末端烯烃。我们一起展示了维生素 B 12是开发温和烯烃形成反应的强大平台。
• Olefin-Assisted Iron-Catalyzed Alkylation of Aryl Chlorides
  作者：Samet Gülak、Tim N. Gieshoff、Axel Jacobi von Wangelin

  DOI：10.1002/adsc.201300095

  日期：2013.8.12

  AbstractA selective and operationally simple iron‐catalyzed cross‐coupling of aryl chlorides with alkylmagnesium halides has been developed. The reaction tolerates various functional groups and exhibits high chemoselectivity even in the presence of aryl bromides. Mechanistic studies indicate the essential role of the olefin substituent for substrate activation. Competing polymerization and reduction are effectively suppressed.magnified image
• Novel N-(3-hydroxy-4-piperidinyl)benzamide derivatives
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0076530B1

  公开（公告）日：1985-12-11