N-(4-(allyloxy)phenyl)benzamide | 51515-28-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-(allyloxy)phenyl)benzamide
• 英文别名: N-[4-(allyloxy)phenyl]benzamide；N-(4-prop-2-enoxyphenyl)benzamide
• CAS: 51515-28-7
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: UXYYSMPESQFIIP-UHFFFAOYSA-N

物化性质

• 熔点：
  150-151 °C(Solv: ethanol (64-17-5))
• 沸点：
  328.4±25.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-(allyloxy)phenyl)benzamide 在 氢气 、 potassium carbonate 、 N,N-二乙基苯胺 作用下， 以 丙酮 为溶剂， 反应 18.0h， 生成 4-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyloxy)-3-allylphenylbenzenamide
  参考文献：
  名称：

  Synthesis and SAR studies of 3-allyl-4-prenyloxyaniline amides as potent 15-lipoxygenase inhibitors

  摘要：

  15-Lipoxygenases are one of the nonheme iron-containing proteins with ability of unsaturated lipid peroxidation in animals and plants. The critical role of the enzymes in formation of inflammations, sensitivities and some of cancers has been demonstrated in mammalians. Importance of the 15-lipoxygenases leads to development of mechanistic studies, products analysis and synthesis of their inhibitors. In this work new series of the 3-allyl-4-allyoxyaniline amides and 3-allyl-4-prenyloxyaniline amides were designed, synthesized and their inhibitory potency against soybean 15-lipoxygenase were determined. Among the synthetic amides, 3-allyl-4-(farnesyloxy)-adamantanilide showed the most potent inhibitory activity by IC50 value of 0.69 mu M. SAR studies showed that in spite of prenyl length increases, the effects of the amide size and its electronic properties on the inhibitory potency became predominant. The SAR studies was also showed that the orientation of allyl and prenyloxy moieties toward Fe core of the SLO active site pocket is the most suitable location for enzyme inhibition. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.025
• 作为产物：
  描述：

  1-allyloxy-4-nitrobenzene 在 tin(II) chloride dihdyrate 、 氯甲酸乙酯 、 三乙胺 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 1.08h， 生成 N-(4-(allyloxy)phenyl)benzamide
  参考文献：
  名称：

  Synthesis and SAR studies of 3-allyl-4-prenyloxyaniline amides as potent 15-lipoxygenase inhibitors

  摘要：

  15-Lipoxygenases are one of the nonheme iron-containing proteins with ability of unsaturated lipid peroxidation in animals and plants. The critical role of the enzymes in formation of inflammations, sensitivities and some of cancers has been demonstrated in mammalians. Importance of the 15-lipoxygenases leads to development of mechanistic studies, products analysis and synthesis of their inhibitors. In this work new series of the 3-allyl-4-allyoxyaniline amides and 3-allyl-4-prenyloxyaniline amides were designed, synthesized and their inhibitory potency against soybean 15-lipoxygenase were determined. Among the synthetic amides, 3-allyl-4-(farnesyloxy)-adamantanilide showed the most potent inhibitory activity by IC50 value of 0.69 mu M. SAR studies showed that in spite of prenyl length increases, the effects of the amide size and its electronic properties on the inhibitory potency became predominant. The SAR studies was also showed that the orientation of allyl and prenyloxy moieties toward Fe core of the SLO active site pocket is the most suitable location for enzyme inhibition. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.025

文献信息

• Enhanced Reactivity of Aerobic Diimide Olefin Hydrogenation with Arylboronic Compounds: An Efficient One-Pot Reduction/Oxidation Protocol
  作者：Surojit Santra、Joyram Guin

  DOI：10.1002/ejoc.201501222

  日期：2015.11

  The process is based on the utilization of a readily available Lewis acidic arylboron compound, which evades common problems associated with the catalyst-free aerobic hydrogenation of olefins with diimide. Using an operationally simple procedure, the protocol smoothly delivers phenol derivatives and various alkanes in excellent yields with remarkable functional group compatibility. The method allows

  提出了一种无催化剂且有效的方法，用于同时将烯烃氢化和芳基硼酸酯氧化为具有水合肼和分子氧的酚类。该工艺基于利用容易获得的路易斯酸性芳基硼化合物，避免了与烯烃与二酰亚胺的无催化剂有氧氢化相关的常见问题。使用操作简单的程序，该协议以优异的收率顺利提供苯酚衍生物和各种烷烃，并具有显着的官能团兼容性。该方法允许将反应放大至 1 g 起始材料。
• Design, synthesis and SAR studies of 4-allyoxyaniline amides as potent 15-lipoxygensae inhibitors
  作者：Seyed Mohammad Seyedi、Zeinab Jafari、Neda Attaran、Hamid Sadeghian、Mohammad Reza Saberi、Mohammad Mahdi Riazi

  DOI：10.1016/j.bmc.2008.12.065

  日期：2009.2

  A group of 4-allyloxyaniline amides 5a-o were designed, synthesized and evaluated as potential inhibitors of soybean 15-lipoxygenase (SLO) on the basis of eugenol and esteragol structures. Compound 5e showed the best IC(50) in SLO inhibition (IC(50) = 0.67 +/- 0.06 mu M). All compounds were docked in SLO active site retrieved from RCSB Protein Data Bank (PDB entry: 1IK3) and showed that allyloxy group of compounds is oriented towards the Fe(3+)-OH moiety in the active site of enzyme and fixed by hydrogen bonding with two conserved His(513) and Gln(716). It is resulted that molecular volume of the amide moiety would be a major factor in inhibitory potency variation of the synthetic amides, where the hydrogen bonding of the amide group could also involve in the activity of the inhibitors. (c) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and SAR studies of 3-allyl-4-prenyloxyaniline amides as potent 15-lipoxygenase inhibitors
  作者：Atena Jabbari、Mahdieh Davoodnejad、Maliheh Alimardani、Amir Assadieskandar、Ali Sadeghian、Hadi Safdari、Jebraeel Movaffagh、Hamid Sadeghian

  DOI：10.1016/j.bmc.2012.07.025

  日期：2012.9

  15-Lipoxygenases are one of the nonheme iron-containing proteins with ability of unsaturated lipid peroxidation in animals and plants. The critical role of the enzymes in formation of inflammations, sensitivities and some of cancers has been demonstrated in mammalians. Importance of the 15-lipoxygenases leads to development of mechanistic studies, products analysis and synthesis of their inhibitors. In this work new series of the 3-allyl-4-allyoxyaniline amides and 3-allyl-4-prenyloxyaniline amides were designed, synthesized and their inhibitory potency against soybean 15-lipoxygenase were determined. Among the synthetic amides, 3-allyl-4-(farnesyloxy)-adamantanilide showed the most potent inhibitory activity by IC50 value of 0.69 mu M. SAR studies showed that in spite of prenyl length increases, the effects of the amide size and its electronic properties on the inhibitory potency became predominant. The SAR studies was also showed that the orientation of allyl and prenyloxy moieties toward Fe core of the SLO active site pocket is the most suitable location for enzyme inhibition. (C) 2012 Elsevier Ltd. All rights reserved.