(E)-2'-hydroxy-3-nitrochalcone

• 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: (E)-2'-hydroxy-3-nitrochalcone
• 英文别名: (E)-1-(2-hydroxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one；2'-hydroxy-3-nitrochalcone；1-(2-Hydroxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: JIPHTRVDCNBHOR-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2'-hydroxy-3-nitrochalcone 在 双氧水 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以91%的产率得到3-硝基肉桂酸
  参考文献：
  名称：

  Solvent-Dependent Regioselective Oxidation oftrans-Chalcones using Aqueous Hydrogen Peroxide

  摘要：

  A novel method for regioselective oxidation of trans-chalcones with hydrogen peroxide in acetonitrile to afford cinnamic acids is reported. Only trans-beta-arylacrylic acids were observed. A wide range of functionalized products can be effectively produced from various chalcones in good to excellent yields.

  DOI：

  10.5935/0103-5053.20130063
• 作为产物：
  描述：

  3-hydroxy-1-(2-hydroxyphenyl)-3-(3-nitrophenyl)-propan-1-one 在 oxonium 作用下， 生成 (E)-2'-hydroxy-3-nitrochalcone
  参考文献：
  名称：

  Synthesis and preliminary biological evaluation of 4,6-disubstituted 3-cyanopyridin-2(1H)-ones, a new class of calcium entry blockers

  摘要：

  The preparation of 3-cyano-4,6-diaryl-pyridin-2(1H)-ones 4a . h, calcium entry blockers related to diltiazem, is described starting from 1,3-diaryl-2-propen-1-ones 5. On preliminary pharmacological tests all compounds are active and some of them show calcium antagonistic activity superior or comparable to diltiazem. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00361-9

文献信息

• NHC-Catalyzed Reaction of Enals with Hydroxy Chalcones: Diastereoselective Synthesis of Functionalized Coumarins
  作者：Anup Bhunia、Atanu Patra、Vedavati G. Puranik、Akkattu T. Biju

  DOI：10.1021/ol400562z

  日期：2013.4.5

  The N-heterocyclic carbene-catalyzed annulation of enals with 2′-hydroxy chalcones afford cyclopentane-fused coumarin derivatives with an excellent level of diastereocontrol. The reaction tolerates a broad range of functional groups; 25 examples are given, and a preliminary mechanistic investigation is provided.

  用2'-羟基查耳酮对烯进行N杂环卡宾催化的环化反应，可得到环戊烷稠合的香豆素衍生物，具有极佳的非对映异构控制水平。该反应可耐受各种官能团。给出了25个示例，并提供了初步的机械研究。
• Mosquito larvicidal studies of some chalcone analogues and their derived products: structure–activity relationship analysis
  作者：Naznin A. Begum、Nayan Roy、Rajibul A. Laskar、Kunal Roy

  DOI：10.1007/s00044-010-9305-6

  日期：2011.3

  A series of chalcone analogues and some of their derivatives were synthesized and subjected to the mosquito larvicidal study. Chalcones having electron releasing group(s) on either ring A or ring B showed high toxicity. Electron withdrawing group(s), especially at ring B, reduced the activity of chalcones. The activity was abruptly decreased due to replacement of ring A by CH3, extension of conjugation

  合成了一系列查尔酮类似物及其一些衍生物，并进行了蚊幼虫研究。在环A或环B上均具有电子释放基团的查耳酮显示出高毒性。吸电子基团，特别是在B环上，降低了查耳酮的活性。由于通过CH 3取代环A ，扩展结合或衍生化查耳酮的α，β-不饱和酮部分，其活性突然降低。这些化合物的定量结构-活性关系（QSAR）研究使用各种空间，电子和物理化学参数进行。使用线性和样条选项的遗传函数近似作为开发QSAR模型的化学计量工具。
• Synthesis and cdc25B inhibitory activity evaluation of chalcones
  作者：Fei Zhao、Qing-Jie Zhao、Jing-Xia Zhao、Da-Zhi Zhang、Qiu-Ye Wu、Yong-Sheng Jin

  DOI：10.1007/s10600-013-0563-7

  日期：2013.5

  A library of sixty-five chalcones was prepared for screening against the protein phosphatase, cdc25B. From this library, thirteen compounds were found having good inhibitory activity. Two compounds have excellent activity and can be used for the design of more potent antiproliferative agents.

  制备了一个包含六十五种查尔酮的库，用于针对蛋白磷酸酶cdc25B进行筛选。从这个库中，发现了十三种具有良好抑制活性的化合物。其中两种化合物表现出极佳的活性，可用于设计更有效的抗增殖剂。
• Catalytic Enantioselective Synthesis of 2-Aryl Chromenes and Related Phosphoramidite Ligands and Catalyst Compounds
  申请人：Northwestern University

  公开号：US20150315168A1

  公开（公告）日：2015-11-05

  Methods to access 2-aryl chromene compounds via an asymmetric catalytic process.

  通过不对称催化过程访问2-芳基色素化合物的方法。
• Synthesis and antibacterial activity of chalcone derivatives containing thioether triazole
  作者：Ying Chen、Pu Li、Mei Chen、Jun He、Shijun Su、Ming He、Hua Wang、Wei Xue

  DOI：10.1002/jhet.3755

  日期：2020.3

  agricultural production. In this study, a series of novel chalcone derivatives containing thioether triazoles were designed and synthesized. The structures of the novel compounds were systematically characterized via 1H‐NMR, 13C‐NMR, and HRMS. Moreover, the antibacterial activity results showed that E10, E11, E15, and E16 have adequate antibacterial activities against Xoo, Rs, and Xac. Among the different compounds

  米糠黄单胞菌的感染。Oryzae（Xoo），Ralstonia solanacearum（Rs）和Xanthomonas axonopodis pv。柠檬（Xac）已成为农业生产中的主要问题。在这项研究中，设计并合成了一系列新型的含硫醚三唑的查尔酮衍生物。通过 1 H-NMR，13 C-NMR和HRMS系统地表征了新型化合物的结构。此外，抗菌活性结果表明，E 10，E 11，E 15和E 16对Xoo，Rs和Xac具有足够的抗菌活性。在不同的化合物中，E 15对Xac表现出显着的抑制作用，EC 50为9.1μg.mL -1，比商品试剂比美噻唑（54.9μg.mL -1）更好。另外，通过扫描电子显微镜（SEM）研究了目标化合物E 15对Xac的可能的抗菌机理。