2-(4-methoxyphenyl)-3-methyl-4H-chromen-4-one | 55456-74-1

• 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-methoxyphenyl)-3-methyl-4H-chromen-4-one
• 英文别名: 2-(4-Methoxyphenyl)-3-methylchromen-4-one
• CAS: 55456-74-1
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: XRAIJWPVKRLSBE-UHFFFAOYSA-N

物化性质

• 熔点：
  112-114 °C
• 沸点：
  408.8±45.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-3-methyl-4H-chromen-4-one 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 5.0h， 生成 3-(bromomethyl)-4'-methoxyflavone
  参考文献：
  名称：

  Lead Optimization Providing a Series of Flavone Derivatives as Potent Nonsteroidal Inhibitors of the Cytochrome P450 Aromatase Enzyme

  摘要：

  Following our SAR studies on aromatase inhibitors, new compounds were designed by appropriately modifying the structure of flavone 1 using our previously reported CoMFA model. While the introduction of substituents on the 2-phenyl ring alone did not cause improvement in potency, these modifications and the removal of the 7-methoxy group led to compounds showing inhibitory activity in the nanomolar range, comparable to the marketed drug fadrozole.

  DOI：

  10.1021/jm060186y
• 作为产物：
  描述：

  1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)-2-methylprop-2-en-1-one 在 碘 作用下， 以 二甲基亚砜 为溶剂， 以85%的产率得到2-(4-methoxyphenyl)-3-methyl-4H-chromen-4-one
  参考文献：
  名称：

  Jayashree; Alam, Afroze; Kumar, D. Vijay, Indian Journal of Heterocyclic Chemistry, 2010, vol. 19, # 3, p. 237 - 240

  摘要：

  DOI：

文献信息

• Iron(III)-Catalyzed Peroxide-Mediated C-3 Functionalization of Flavones
  作者：Bilal Ahmad Mir、Arghya Banerjee、Sourav Kumar Santra、Suresh Rajamanickam、Bhisma K. Patel

  DOI：10.1002/adsc.201600565

  日期：2016.11.3

  An iron(III)‐catalyzed C‐3 functionalization of flavones has been achieved using tert‐butyl peroxybenzoate (TBPB)/potassium persulphate (K2S2O8) oxidant combinations with a suitable solvent. In the presence of iron(III)/tert‐butyl peroxybenzoate/potassium persulphate, the reaction of flavones in cycloalkanes afforded exclusive C‐3 cycloalkylation via C –C coupling, whereas the solvent N,N‐dialkylformamide

  使用过氧苯甲酸叔丁酯（TBPB）/过硫酸钾（K 2 S 2 O 8）氧化剂和合适的溶剂可实现黄酮的铁（III）催化C-3官能化。在存在铁（III）/叔丁基过氧化苯甲酸酯/过硫酸钾，黄酮在环烷烃反应，得到独家C-3环烷基化通过Ç -C耦合，而溶剂Ñ，Ñ -dialkylformamide提供的C-3的酰胺化通过Ç -C耦合。在相同的反应条件下，仅通过将溶剂切换为氯苯，即可得到C-3甲基化的黄酮，其中过氧苯甲酸叔丁酯（TBPB）是甲基的来源。
• One-Pot Synthesis of 3-Methylflavones and Their Transformation into (E)-3-Styrylflavones via Wittig Reactions
  作者：Diana Pinto、Artur Silva、Djenisa Rocha

  DOI：10.1055/s-0033-1340013

  日期：——

  An efficient one-pot synthesis of 3-methylflavone derivatives is established. Furthermore, their transformation into phosphorus ylides, which are then used in the diastereoselective synthesis of (E)-styrylflavones through Wittig reactions, is also studied.
• Synthesis of 3-methylflavones and their antioxidant and antibacterial activities
  作者：B. S. Jayashree、Afroze Alam、Yogendra Nayak、D. Vijay Kumar

  DOI：10.1007/s00044-011-9725-y

  日期：2012.8

  An attempt was made to synthesise newer 3-methylflavones with various substitution on the ring A and B of 2-phenylchromen-4-one. They were evaluated for antioxidant activity and antibacterial activity against the Gram-positive and Gram-negative bacteria. Five test compounds exhibited DPPH radical scavenging activity with IC50 below 100 mu g/ml, and the same test compounds exhibited 50-100% growth inhibition in Gram-positive bacteria against standard Amoxicillin.
• Synthesis of functionalized flavones from 3-halo-2-(methylthio)-4H-chromen-4-ones
  作者：Amr Elagamy、Laila K. Elghoneimy、Reem K. Arafa、Ramendra Pratap

  DOI：10.1016/j.tetlet.2022.153882

  日期：2022.6

  A simple and efficient method for the synthesis of flavones was achieved by selective sulfide Liebeskind-Srogl cross-coupling reaction of 2-(methylthio)-4H-chromen-4-ones and 3-halo-2-(methylthio)-4H-chromen-4-ones with arylboronic acids. This method is the first example of employing Liebeskind-Srogl coupling for the synthesis of flavones. Various aryl groups can be directly installed to the chromone
• MULVAGH D.; MEEGAN M. J.; DONNELLY D., J. CHEM. RES. SYNOP., 1979, NO 4, 137, (M 1713-1731)
  作者：MULVAGH D.、 MEEGAN M. J.、 DONNELLY D.

  DOI：——

  日期：——