6-(3-dimethylaminophenoxy)hexyl bromide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-(3-dimethylaminophenoxy)hexyl bromide
• 英文别名: 3-(6-bromohexoxy)-N,N-dimethylaniline
• 化学式: C₁₄H₂₂BrNO
• 分子量: 300.239
• InChiKey: DGVZODAWPMBXOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(3-dimethylaminophenoxy)hexyl bromide 生成 4-[6-(3-Dimethylaminophenoxy)hexyl]-3,5-heptanedione
  参考文献：
  名称：

  Aryloxyalkyl diketones

  摘要：

  烷氧基烷基二酮和酮酯是一种有用的杀虫剂和抗病毒剂，可以从烷氧基烷基卤代物和二酮或酮酯的碱金属烯醇盐，或者从卤代烷基-二酮和酚的碱金属盐制备而成。

  公开号：

  US04031246A1
• 作为产物：
  描述：

  6-溴正己醇 、 3-羟基-N,N-二甲基苯胺 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到6-(3-dimethylaminophenoxy)hexyl bromide
  参考文献：
  名称：

  烯烃辅助铁催化的芳基氯化烷基化

  摘要：

  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

  DOI：

  10.1002/adsc.201300095

文献信息

• Dialkylamino- and dialkylaminoalkoxy-substituted aryloxyalkyl diketones
  申请人：Sterling Drug Inc.

  公开号：US04198436A1

  公开（公告）日：1980-04-15

  Dialkylamino- and dialkylaminoalkoxy-substituted aryloxyalkyl diketones, useful as anti-viral agents, are prepared by reacting a dialkylamino-substituted phenoxyalkyl halide with an alkali metal enolate salt of a diketone; or by reacting the corresponding hydroxy-substituted phenoxyalkyl diketone with a dialkylaminoalkyl halide.

  二烷基氨基和二烷基氨基烷氧基取代的芳氧基烷基二酮，可用作抗病毒剂，通过将二烷基氨基取代的苯氧基烷基卤代烃与二酮的碱金属烯醇盐反应来制备；或通过将相应的羟基取代的苯氧基烷基二酮与二烷基氨基烷基卤代烃反应来制备。
• Design, Synthesis, and Structure−Activity Relationship of Pyridyl Imidazolidinones:  A Novel Class of Potent and Selective Human Enterovirus 71 Inhibitors
  作者：Kak-Shan Shia、Wen-Tai Li、Chung-Ming Chang、Ming-Chu Hsu、Jyh-Haur Chern、Max K. Leong、Sung-Nien Tseng、Chung-Chi Lee、Yen-Chun Lee、Shu-Jen Chen、Kuan-Chang Peng、Huan-Yi Tseng、Yi-Ling Chang、Chia-Liang Tai、Shin-Ru Shih

  DOI：10.1021/jm010536a

  日期：2002.4.1

  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.
• US4198436A
  申请人：——

  公开号：US4198436A

  公开（公告）日：1980-04-15
• 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
• Aryloxyalkyl diketones
  申请人：Sterling Drug Inc.

  公开号：US04031246A1

  公开（公告）日：1977-06-21

  Aryloxyalkyl diketones and keto-esters, useful as pesticidal and anti-viral agents, are prepared from an aryloxyalkyl halide and an alkali metal enolate salt of a diketone or keto-ester, or from a haloalkyl-diketone and an alkali metal salt of a phenol.

  烷氧基烷基二酮和酮酯是一种有用的杀虫剂和抗病毒剂，可以从烷氧基烷基卤代物和二酮或酮酯的碱金属烯醇盐，或者从卤代烷基-二酮和酚的碱金属盐制备而成。