(E)-3-(3,4-dichlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one | 845644-17-9

• 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)-3-(3,4-dichlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 845644-17-9
• 化学式: C₁₅H₁₀Cl₂O₂
• 分子量: 293.149
• InChiKey: QNLAWVVTEVXBHF-SOFGYWHQSA-N

物化性质

• 沸点：
  464.5±45.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(3,4-dichlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 在 碘 作用下， 以 二甲基亚砜 为溶剂， 生成 2-(3,4-dichlorophenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives

  摘要：

  A series of chrysin derivatives were prepared and evaluated for their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production. Chrysin derivatives were prepared from 2-hydroxyacetophenone, 2,4-dihydroxyacetophenone and 2,6-dihydroxyacetophenone in 2 to 4 steps, respectively. Methxoylated chrysin derivatives were converted to the corresponding hydroxylated chrysin derivatives by the reaction with BBr3 in good yields. The inhibitory activity of the chrysin derivatives against prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells was measured. We found that chrysin derivatives with 3',4'-dichloro substituents (5e, 6e and 7e) exhibited good inhibitory activity of prostaglandin production. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.087
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 pyridium para-toluenesulfonate 、 barium hydroxide octahydrate 、 对甲苯磺酸 作用下， 反应 4.0h， 生成 (E)-3-(3,4-dichlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  合成查耳酮可作为潜在的抗炎药和癌症化学预防剂。

  摘要：

  为了开发有效的抗炎药和癌症化学预防剂，通过适当的苯乙酮与适当的芳族醛的克莱森-施密特缩合反应制备了一系列查耳酮，或通过与适当的烷基溴反应的适当的二氢查耳酮制备了一系列查耳酮，或通过一锅法制备通过在碱性氧化铝上超声搅拌获得苯乙酮和方便的芳香醛。测试了合成产物对肥大细胞，嗜中性粒细胞，巨噬细胞和小胶质细胞活化的抑制作用。进一步评估了巨噬细胞和小胶质细胞中NO产生的有效抑制剂对几种人类癌细胞系的体外细胞毒性作用。2'-羟基查耳酮1-3和2'，5' -二羟基查耳酮7对用甲酰-Met-Leu-Phe（fMLP）/细胞松弛素B（CB）刺激的大鼠嗜中性粒细胞释放β-葡萄糖醛酸苷酶或溶菌酶具有有效的抑制作用。响应fMLP / CB，两个2'-羟基查耳酮（1和3）对大鼠中性粒细胞中超氧阴离子的生成具有有效的抑制作用。先前报道的查耳酮5、6和12在脂多糖（LPS）/干扰素-γ（IFN-γ）激活的N9小胶质细胞或LPS激活的RAW

  DOI：

  10.1016/j.ejmech.2004.09.006

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。
• 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。
• Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride
  作者：Motofumi Miura、Karin Shigematsu、Masaharu Toriyama、Shigeyasu Motohashi

  DOI：10.1016/j.tetlet.2021.153480

  日期：2021.11

  flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.

  在温和条件下，从相应的羟基查耳酮与催化量的氟化铯水溶液通过氧杂-迈克尔加成容易合成总共 36 种黄烷酮，其中包括多环芳环和杂环。该方法可用于作为 SARS-CoV-2 刺突蛋白的已知强效抑制剂圣草酚的可扩展合成。
• 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。
• Catalytic enantioselective synthesis of 2-aryl chromenes and related phosphoramidite ligands and catalyst compounds
  申请人：Northwestern University

  公开号：US10308624B2

  公开（公告）日：2019-06-04

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

  通过不对称催化过程获得 2-芳基色烯化合物的方法。