(E)-1-(4-chloro-2-hydroxyphenyl)-3-phenylprop-2-en-1-one | 52923-31-6

• 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)-1-(4-chloro-2-hydroxyphenyl)-3-phenylprop-2-en-1-one
• 英文别名: 4'-chloro-2'-hydroxy-trans-chalcone；4'-Chlor-2'-hydroxy-trans-chalkon；2'-Hydroxy-4'-chlorochalcone
• CAS: 52923-31-6
• 化学式: C₁₅H₁₁ClO₂
• 分子量: 258.704
• InChiKey: ZAHMVLOKJSGFLB-RMKNXTFCSA-N

物化性质

• 熔点：
  128.6-129.3 °C(Solv: ethanol (64-17-5))
• 沸点：
  431.8±45.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 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)-1-(4-chloro-2-hydroxyphenyl)-3-phenylprop-2-en-1-one 在 双氧水 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以88%的产率得到肉桂酸
  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：

  7-chloro-2-phenylchroman-4-one 、 苯 以2%的产率得到
  参考文献：
  名称：

  MATSUSHIMA RYOKA; KISHIMOTO TSUNEO; SUZUKI MORIO; MORIOKA MOTONOBU; MIZUN+, BULL. CHEM. SOC. JAP., 1980, 53, NO 10, 2938-2942

  摘要：

  DOI：

文献信息

• 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。
• SYNTHESIS OF α-AZIDO-2′-HYDROXYCHALCONES FROM CHALCONE DIBROMIDES WITH AZIDE ION
  作者：Tamás Patonay、József Jekö、Éva Rimán

  DOI：10.1081/scc-120006013

  日期：2002.1

  ABSTRACT The reaction of the 2′-hydroxychalcone dibromides with azide ion was found to afford various products such as α-azido-2′-hydroxychalcones, flavones, aurones, isoxazoles or the parent chalcones depending on the substituent pattern of the substrate. Efficient transformation of α-azido-2′-hydroxychalcones to 3-amino-2-substituted chromones was also demonstrated.

  摘要 2'-羟基查尔酮二溴化物与叠氮离子的反应被发现提供各种产物，如 α-叠氮基-2'-羟基查尔酮、黄酮、aurone、异恶唑或母体查耳酮，这取决于底物的取代模式。还证明了 α-叠氮基-2'-羟基查耳酮向 3-氨基-2-取代的色酮的有效转化。
• Halogenated flavanones as potential apoptosis-inducing agents: Synthesis and biological activity evaluation
  作者：Maliheh Safavi、Nasim Esmati、Sussan Kabudanian Ardestani、Saeed Emami、Soheila Ajdari、Jamshid Davoodi、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1016/j.ejmech.2012.10.043

  日期：2012.12

  A series of halogenated flavanones were synthesized from 2-hydroxychalcones and tested for their cytotoxicity against a panel of human cancer cell lines. Among the synthesized compounds, 3',7-dichloroflavanone (2d) showed the highest activity against MCF-7, LNCaP, PO, Hep-G2, KB and SK-N-MC cells. However, 3',6-dichloroflavanone (2g) with IC50 value of 2.9 +/- 0.9 mu M was the most potent compound against MDA-MB-231 cells, being approximately 12 times more active than etoposide as reference drug. According to the flow-cytometric analysis, compound 2g can induce apoptosis by 66.19 and 21.37% in PO and MDA-MB-231 cells, respectively. The results of acridine orange/ethidium bromide staining and TUNEL assay suggested that the cytotoxic activity of this compound in PO and MDA-MB-231 cells occurs via apoptosis. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Tsumaki et al., Nippon Kagaku Zasshi, 1951, vol. 72, p. 368
  作者：Tsumaki et al.

  DOI：——

  日期：——
• Deoxygenation of α,β-unsaturated acylphenols through ethyl o-acylphenylcarbonates with Luche reduction
  作者：Hu Yuan、Hao Chen、Huizi Jin、Bo Li、Rongcai Yue、Ji Ye、Yunheng Shen、Lei Shan、Qingyan Sun、Weidong Zhang

  DOI：10.1016/j.tetlet.2013.02.109

  日期：2013.5

  An efficient protocol for deoxygenation of alpha,beta-unsaturated acylphenols through ethyl o-acylphenylcarbonates with Luche reduction is described. The reaction shows very good selectivity and tolerates a wide range of functionalities on alpha,beta-unsaturated acylphenols, giving corresponding 2-allylphenols in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.