2-(4-(benzyloxy)-3-methoxyphenyl)-4H-chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-(benzyloxy)-3-methoxyphenyl)-4H-chromen-4-one
• 英文别名: 2-(3-Methoxy-4-phenylmethoxyphenyl)chromen-4-one
• 化学式: C₂₃H₁₈O₄
• 分子量: 358.394
• InChiKey: UYLKCPWVEZPTOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-(benzyloxy)-3-methoxyphenyl)-4H-chromen-4-one 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 以87 %的产率得到2-(4-羟基-3-甲氧基苯基)-4H-色烯-4-酮
  参考文献：
  名称：

  Anti-tyrosinase flavone derivatives and their anti-melanogenic activities: Importance of the β-phenyl-α,β-unsaturated carbonyl scaffold

  摘要：

  DOI：

  10.1016/j.bioorg.2023.106504
• 作为产物：
  描述：

  [E]-3-(m-methoxy-p-benzyloxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 在 碘 作用下， 以 二甲基亚砜 为溶剂， 以86 %的产率得到2-(4-(benzyloxy)-3-methoxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Anti-tyrosinase flavone derivatives and their anti-melanogenic activities: Importance of the β-phenyl-α,β-unsaturated carbonyl scaffold

  摘要：

  DOI：

  10.1016/j.bioorg.2023.106504

文献信息

• An efficient oxidative conversion of 2-aryl-2H-chromenes to the corresponding flavones by tert-butylhydroperoxide and copper bromide
  作者：Dipanwita Banerjee、Utpal Kayal、Gourhari Maiti

  DOI：10.1016/j.tetlet.2016.03.006

  日期：2016.4

  A simple and efficient method has been developed for the facile oxidation of chromenes to the corresponding flavones by tert-butylhydroperoxide (TBHP) in the presence of copper(II) bromide catalyst in toluene at 80 °C in a very short time. The reaction demonstrates excellent reactivity, functional group tolerance, and good to excellent yields without using conventional strong oxidizing agents.

  已经开发了一种简单有效的方法，用于在80℃下于很短时间内在甲苯中存在溴化铜（II）的情况下，通过叔丁基氢过氧化物（TBHP）轻松地将二甲基苯酮氧化为相应的黄酮。该反应显示出优异的反应性，官能团耐受性以及良好至优异的产率，而无需使用常规的强氧化剂。
• [EN] POLYPHENOL ANALOGS TO TREAT ISCHEMIA<br/>[FR] ANALOGUES DE POLYPHÉNOL POUR TRAITER UNE ISCHÉMIE
  申请人：LAPCHAK PAUL A

  公开号：WO2013025484A1

  公开（公告）日：2013-02-21

  The present invention provides methods of use of polyphenol compounds for treating, preventing, mitigating and delaying ischemia or a condition where ischemia occurs. In one embodiment, the method comprises providing a polyphenol analog; and administering the polyphenol analog to a subject to treat ischemia or a condition where ischemia occurs. Various embodiments of the present invention are useful for the treatment of patients having, or at risk for, any of (1) ischemic stroke, (2) hemorrhagic stroke, (3) cardiovascular disease, (4) ischemia related spinal cord injury, (5) ischemia in diabetic patients, or (6) embolic stroke.. For example, use of the polyphenol compounds can maintain glutathione levels in the patient.

  本发明提供了使用多酚化合物治疗、预防、缓解和延迟缺血或发生缺血状况的方法。在一个实施方式中，该方法包括提供一种多酚类似物；并将该多酚类似物给予受试者以治疗缺血或发生缺血状况。本发明的各种实施方式适用于治疗患有或有风险患有以下任何一种疾病的患者：（1）缺血性中风，（2）出血性中风，（3）心血管疾病，（4）与缺血有关的脊髓损伤，（5）糖尿病患者的缺血，或（6）栓塞性中风。例如，使用多酚化合物可以维持患者的谷胱甘肽水平。
• [EN] NEUROPROTECTIVE POLYPHENOL ANALOGS<br/>[FR] ANALOGUES DU POLYPHÉNOL NEUROPROTECTEURS
  申请人：SCHUBERT DAVID R

  公开号：WO2013025498A1

  公开（公告）日：2013-02-21

  The present invention provides neuroprotective polyphenol compounds, which can be synthetic analogs of fisetin, baicalein or chlorogenic acid, that maintain neuroprotective, anti-inflammatory, glutathione promoting, and/or antioxidant properties. The neuroprotective polyphenol compounds are useful for promoting, enhancing and/or increasing neuron protection, growth and/or regeneration. The polyphenol compounds further find use for increasing and or maintaining intracellular glutathione (GSH) levels. The polyphenol compounds are also useful for treating, preventing, mitigating and/or delaying neurodegenerative conditions, including diabetes, Parkinson's disease, Huntington's disease, Alzheimer's disease, non-Alzherimer's dementias, multiple sclerosis, traumatic brain injury, spinal cord injury or ALS.

  本发明提供了神经保护多酚化合物，可以是嘌呤、黄芩素或绿原酸的合成类似物，这些化合物具有保持神经保护、抗炎、促进谷胱甘肽以及抗氧化性能。这些神经保护多酚化合物可用于促进、增强和/或增加神经元的保护、生长和/或再生。多酚化合物还可用于增加和/或维持细胞内谷胱甘肽（GSH）水平。多酚化合物还可用于治疗、预防、缓解和/或延缓神经退行性疾病，包括糖尿病、帕金森病、亨廷顿病、阿尔茨海默病、非阿尔茨海默病性痴呆、多发性硬化症、创伤性脑损伤、脊髓损伤或肌萎缩侧索硬化症（ALS）。
• Regiospecific Carbonylative Annulation of Iodophenol Acetates and Acetylenes To Construct the Flavones by a New Catalyst of Palladium−Thiourea−dppp Complex
  作者：Hua Miao、Zhen Yang

  DOI：10.1021/ol000087t

  日期：2000.6.1

  [GRAPHICS]Regiospecific carbonylative annulation of sigma-iodophenol acetates and acetylenes mediated by palladium-thiourea-dppp complex in the presence of base at 40 degrees C under a balloon pressure of CO generates diversified flavones in high yields. This newly developed synthetic technology provides a highly efficient method for potential application to the combinatorial synthesis of those heterocycles on the solid support.
• NEUROPROTECTIVE POLYPHENOL ANALOGS
  申请人：Salk Institute for Biological Studies

  公开号：EP2741609A1

  公开（公告）日：2014-06-18