3-(4′′-dimethylaminophenyl)-1-(3′-nitrophenyl)propenone | 20679-21-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(4′′-dimethylaminophenyl)-1-(3′-nitrophenyl)propenone
• 英文别名: 4-dimethylamino-3'-nitro-trans-chalcone；4-Dimethylamino-3'-nitro-trans-chalkon；(E)-3-(4-dimethylaminophenyl)-1-(3-nitrophenyl)prop-2-en-1-one；(E)-3-[4-(dimethylamino)phenyl]-1-(3-nitrophenyl)prop-2-en-1-one
• CAS: 20679-21-4
• 化学式: C₁₇H₁₆N₂O₃
• 分子量: 296.326
• InChiKey: MAUZGQVCAOWWHD-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对二甲氨基苯甲醛 、 间硝基苯乙酮 在 silica gel supported sulfuric acid 作用下， 以 neat (no solvent) 为溶剂， 反应 1.5h， 以76%的产率得到3-(4′′-dimethylaminophenyl)-1-(3′-nitrophenyl)propenone
  参考文献：
  名称：

  Evaluation of Silica-H2SO4 as an Efficient Heterogeneous Catalyst for the Synthesis of Chalcones

  摘要：

  我们报道了一种高效的二氧化硅-H2SO4介导的合成多种查尔酮的方法，该方法与碱催化的无溶剂条件以及酸或碱催化的回流条件相比，能够以非常好的产率获得目标化合物。

  DOI：

  10.3390/molecules180810081

文献信息

• Synthesis, antimycobacterial activity evaluation, and QSAR studies of chalcone derivatives
  作者：P.M. Sivakumar、S. Prabu Seenivasan、Vanaja Kumar、Mukesh Doble

  DOI：10.1016/j.bmcl.2006.12.112

  日期：2007.3

  In order to develop relatively small molecules as antimycobacterial agents, twenty-five chalcones were synthesized, their activity was evaluated, and quantitative structure-activity relationship (QSAR) was developed. The synthesis was based on the Claisen-Schimdt scheme and the resultant compounds were tested for antitubercular activity by luciferase reporter phage (LRP) assay. Compound C-24 was found to be the most active (similar to 99%) in this series based on the percentage reduction in Relative Light Units at both 50 and 100 mu g/ml levels, followed by compound C-21. Four compounds at the 50 mu g/ml and eight compounds at the 100 mu g/ml showed activity above 90% level. QSAR model was developed between activity and spatial, topological, and ADME descriptors for the 50 mu g/ml data. The statistical measures such as r, r(2), q(2), and F values obtained for the training set were in acceptable range and hence this relationship was used for the test set. The predictive ability of the model is satisfactory (q(2) = 0.56) and it can be used for designing similar group of compounds. (c) 2007 Elsevier Ltd. All rights reserved.