1-phenyl-3-(3,4-dihydroxyphenyl)prop-2-en-1-one | 136068-43-4

• 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: 1-phenyl-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
• 英文别名: 3,4-dihydroxychalcone；3,4-Dihydroxy-chalkon；3-(3,4-dihydroxyphenyl)-1-phenylprop-2-en-1-one
• CAS: 136068-43-4；72704-76-8
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: HHKVOYUYPYZFHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  204-205 °C (decomp)
• 沸点：
  448.6±45.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenyl-3-(3,4-dihydroxyphenyl)prop-2-en-1-one 在 溴 作用下， 以 氯仿 为溶剂， 以78%的产率得到
  参考文献：
  名称：

  新型查耳酮衍生物作为抗菌剂和抗氧化剂的合成，生物学评估，定量SAR和对接研究

  摘要：

  在本研究中，合成了一系列查尔酮衍生物，其中包括17种新化合物。评估了它们对11种细菌的抗菌活性以及使用DPPH清除自由基的活性。所有化合物对革兰氏阳性和革兰氏阴性细菌均显示出显着的抗菌活性。特别是，化合物IIIf强烈抑制金黄色葡萄球菌（JMC 2151）和粪肠球菌（CARS 2011-012），其MIC值分别为6.25 µg mL - 1和12.5 µg mL - 1，与标准抗生素相当。萘啶酸。化合物IIIg也抑制金黄色葡萄球菌具有类似于萘啶酸（6.25微克mL的MIC值- 1）。此外，像萘啶酸（微克毫升25 MIC值- 1），化合物IIIA，IIIc中和IIId的抑制李斯特菌（ATCC 43256），用25 MIC值微克毫升- 1，12.5微克毫升- 1和25μg毫升- 1， 分别。使用物理化学计算进行的定量构效关系（Q-SAR）研究表明，查尔酮衍生物的抗菌活性与预测的物理化学参数具有很好的相关性（log

  DOI：

  10.1515/chempap-2015-0113
• 作为产物：
  描述：

  3,4-双(甲氧基甲氧基)苯甲醛 在 盐酸 、 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 1-phenyl-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis and bioactivity of chalcones and its analogues

  摘要：

  The Vernohia anthelmintica L's extract is one of the most popular Uygur medicines used for vitiligo. It is believed that the chalcone compounds of the plant play an important role in the treatment since they may activate tyrosinase and improve melanin production. In this study, twenty-one chalcones and nine analogues were synthesized in view of three different components of chalcone (A, B ring and a, beta-unsaturated carbonyl). After biological evaluation of their activity on tyrosinase in cell-free systems, the result showed that most compounds (except polyhydroxy chalcones) possess activator effect on the tyrosinase, especially for 13a-15a, 20a and 1 b, which bearing a comparable activity to the positive control 8-MOP. SAR of these tyrosinase activator was summed up for the first time as well. Finally, compound 13a was found to increase melanin contents and tyrosinase activity 1.75 and 1.3 fold, respectively, compared with that of untreated murine B16 cells at the concentration of 40 mu g/mL (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2017.03.018

文献信息

• Evaluation of the radical scavenging activity of a series of synthetic hydroxychalcones towards the DPPH radical
  作者：Iva Todorova、Daniela Batovska、Bistra Stamboliyska、Stoyan Parushev

  DOI：10.2298/jsc100517043t

  日期：——

  Sixteen hydroxychalcones were synthesized in sufficient purity by the Claisen-Schmidt condensation between appropriate acetophenones and aryl aldehydes. All the compounds were evaluated for their ability to scavenge the stable free 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. Important structure-activity relationships were observed that strongly contribute to the knowledge for the design of DPPH radical scavenging chalcones. Relevant theoretical parameters were computed in an attempt to understand and explain the obtained experimental results.

  通过适当的苯乙酮与芳基化合物之间的克莱森-施密特缩合反应，合成了 16 种纯度足够高的羟基查耳酮。 通过适当的苯乙酮和芳基醛之间的克莱森-施密特缩合反应，合成了十六种纯度足够高的羟基查耳酮。 醛缩合合成了十六种纯度足够高的羟基查耳酮。对所有化合物清除稳定的游离 2,2- 二苯基-1-丙酮的能力进行了评估。 稳定的游离 2,2-二苯基-1-苦基肼（DPPH）自由基的能力进行了评估。观察到重要的 结构与活性的关系，这大大有助于 的知识。相关的 理论参数，试图理解和解释所获得的实验结果。 实验结果。
• A one-pot synthesis of substituted pyrido[2,3-b]indolizines
  作者：Fernanda Proença、Marta Costa

  DOI：10.1016/j.tet.2010.12.047

  日期：2011.2

  An efficient and novel approach to the synthesis of substituted pyrido[2,3-b]indolizine-10-carbonitriles was developed. These structures are practically unavailable through previously described methods. The cascade transformation involves the reaction of α,β-unsaturated carbonyl compounds with a stable dimer prepared from 1-(cyanomethyl)pyridinium chloride. The reaction was performed under reflux conditions

  开发了一种高效，新颖的合成取代吡啶并[2,3 - b ]吲哚并嗪-10-腈的方法。这些结构实际上是无法通过前述方法获得的。级联转化涉及α，β-不饱和羰基化合物与由1-（氰甲基）吡啶鎓氯化物制备的稳定二聚体的反应。反应在乙醇/水和乙酸钠存在下于回流条件下进行。该程序代表了对吡啶并[2,3- b ]吲哚嗪核心结构的环保区域选择性方法。
• Novel chalcone derivatives and pharmaceutical compositions comprising the same
  申请人：KAOHSIUNG MEDICAL UNIVERSITY

  公开号：US20040176471A1

  公开（公告）日：2004-09-09

  Disclosed herein are novel chalcone derivatives of formulas (I), (II) and (III): 1 wherein each of the substituents is given the definition as set forth in the Specification and Claims. These compounds are demonstrated to have anti-inflammatory activities and thus can be used in the treatment of an inflammatory disorder in a subject.

  本文披露了式(I)、(II)和(III)的新型查尔酮衍生物：1其中每个取代基的定义如规范和权利要求所述。这些化合物已被证明具有抗炎活性，因此可用于治疗主体的炎症性疾病。
• Process for Producing an Aromatic Unsaturated Compound
  申请人：Wang Weiqi

  公开号：US20080221337A1

  公开（公告）日：2008-09-11

  The present invention provides a process for producing an aromatic unsaturated compound of the formula (4) wherein Ar represents an optionally substituted aromatic group or an optionally substituted heteroaromatic group, and Y represents an electron withdrawing group, which comprises reacting (a) a compound of the formula (1) Ar—H  (1) wherein Ar has the same meaning as defined above with (b) a compound of the formula (2) wherein Y has the same meaning as defined above, and Z represents a lower alkoxy, or a compound of the formula (3) wherein Y and Z have the same meanings as defined above, in the presence of (c) an acid or a compound which generates a mineral acid by its hydrolysis.

  本发明提供了一种制备公式（4）的芳香不饱和化合物的方法，其中Ar代表可选择取代的芳香基团或可选择取代的杂环芳香基团，Y代表电子提取基团，包括以下步骤：(a)将公式（1）的化合物Ar-H（1）与(b)公式（2）的化合物反应，其中Y具有与上述定义相同的含义，Z代表低级烷氧基，或公式（3）的化合物，其中Y和Z具有与上述定义相同的含义，在(c)酸或通过其水解生成矿酸的化合物的存在下。
• PROCESS FOR PRODUCING AN AROMATIC UNSATURATED COMPOUND
  申请人：WANG Weiqi

  公开号：US20090111999A1

  公开（公告）日：2009-04-30

  The present invention provides a process for producing an aromatic unsaturated compound of the formula (4) wherein Ar represents an optionally substituted aromatic group or an optionally substituted heteroaromatic group, and Y represents an electron withdrawing group, which comprises reacting (a) a compound of the formula (1) Ar—H  (1) wherein Ar has the same meaning as defined above with (b) a compound of the formula (2) wherein Y has the same meaning as defined above, and Z represents a lower alkoxy, or a compound of the formula (3) wherein Y and Z have the same meanings as defined above, in the presence of (c) an acid or a compound which generates a mineral acid by its hydrolysis.

  本发明提供了一种生产芳香不饱和化合物的方法，该化合物的化学式为（4），其中Ar表示可选取代的芳香基团或可选取代的杂芳基团，Y表示电子提取基团，该方法包括在(d)酸或生成矿酸的化合物的存在下，将(a)化合物（1）Ar—H（1）（其中Ar的含义如上所定义）与(b)化合物（2）反应，该化合物的化学式为Y与上述定义相同，Z表示较低的烷氧基，或者与(c)化合物（3）反应，该化合物的化学式中Y和Z的含义与上述定义相同。