N-<4-Ethyl-benzoyl>-imidazol | 91391-99-0

• 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-Ethyl-benzoyl>-imidazol
• 英文别名: 1-(4-ethyl-benzoyl)-1H-imidazole；(4-Ethylphenyl)-imidazol-1-ylmethanone
• CAS: 91391-99-0
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: DDWWYACWAKKANL-UHFFFAOYSA-N

物化性质

• 沸点：
  370.8±35.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-<4-Ethyl-benzoyl>-imidazol 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 tetraphosphorus decasulfide 、 六甲基二硅氧烷 、 三乙胺 、 magnesium chloride 作用下， 以 四氢呋喃 、 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 6.0h， 生成 5-(4-ethylphenyl)-3H-1,2-dithiole-3-thione
  参考文献：
  名称：

  Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

  摘要：

  Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine- or H2O2 -induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

  DOI：

  10.1021/acs.jafc.9b06360
• 作为产物：
  描述：

  对乙基苯甲酸 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 生成 N-<4-Ethyl-benzoyl>-imidazol
  参考文献：
  名称：

  Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

  摘要：

  Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine- or H2O2 -induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

  DOI：

  10.1021/acs.jafc.9b06360

文献信息

• Modular synthesis of 1,4-diketones through regioselective bis-acylation of olefins by merging NHC and photoredox catalysis
  作者：Jun-Long Li、Si-Lin Yang、Qing-Song Dai、Hua Huang、Lu Jiang、Qing-Zhu Li、Qi-Wei Wang、Xiang Zhang、Bo Han

  DOI：10.1016/j.cclet.2023.108271

  日期：2023.3

  Efficient and modular synthesis of structurally diverse 1,4-diketones from readily available building blocks represents an essential but challenging task in organic chemistry. Herein, we report a multi-component, regioselective bis-acylation of olefins by merging NHC organocatalysis and photoredox catalysis. With this protocol, a broad range of 1,4-diketones could be rapidly assembled using bench-stable

  从容易获得的结构单元中高效、模块化地合成结构多样的 1,4-二酮是有机化学中一项重要但具有挑战性的任务。在此，我们报道了通过结合 NHC 有机催化和光氧化还原催化实现烯烃的多组分、区域选择性双酰化。通过该方案，可以使用实验室稳定的原料材料快速组装多种 1,4-二酮。通过敏感性筛选进一步评估了该方法的稳健性，并观察到良好的重现性。此外，二酮产物可以很容易地转化为官能化杂环，例如多取代的呋喃、吡咯和哒嗪。机理研究揭示了 NHC 和光氧化还原双催化自由基反应机理。
• Energy-Transfer-Enabled Radical Acylation Using Free Alkyl Boronic Acids through Photo and NHC Dual Catalysis
  作者：Wan-Cong Liu、Xiang Zhang、Lin Chen、Rong Zeng、Yuan-Hang Tian、En-Dian Ma、Ya-Peng Wang、Bin Zhang、Jun-Long Li

  DOI：10.1021/acscatal.3c06027

  日期：2024.3.1

  for ketone synthesis. As an important coupling partner, bench-stable and commercially available alkyl boronic acids are widely used in transition metal catalysis, but they are rarely utilized as radical precursors for acylative coupling reactions. Herein, we reported an energy-transfer-enabled radical acylation using free alkyl boronic acids via NHC/photo dual catalysis. This protocol could efficiently

  交叉偶联反应作为最流行的酮合成方案之一而广受好评。作为重要的偶联伙伴，实验室稳定且市售的烷基硼酸广泛用于过渡金属催化，但很少用作酰化偶联反应的自由基前体。在此，我们报道了通过 NHC/光双催化使用游离烷基硼酸实现能量转移的自由基酰化。该方案可以有效促进烷基硼酸与酰基咪唑之间的铃木型交叉偶联以及烯烃的多组分烷基酰化，从而产生具有结构多样性的各种酮。此外，酮产品可以很容易地转化为大量结构有趣的精细化学品。初步机理研究揭示了独特的自由基反应机理。