(E)-3-(2-methylphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one | 34000-25-4

• 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: (E)-3-(2-methylphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• 英文别名: (E)-1-(2-hydroxyphenyl)-3-(o-tolyl)prop-2-en-1-one；(E)-1-(2-hydroxy-phenyl)-3-o-tolylprop-2-en-1-one；2-methyl,2'-hydroxychalcone；2′-hydroxy-4-methylchalcone；2'-Hydroxy-2-methyl-chalcon；1-(2-Hydroxyphenyl)-3-(2-methylphenyl)prop-2-en-1-one；(E)-1-(2-hydroxyphenyl)-3-(2-methylphenyl)prop-2-en-1-one
• CAS: 34000-25-4
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: ARUMOQJPOFYOBO-ZHACJKMWSA-N

物化性质

• 熔点：
  83 °C

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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-(2-methylphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.17h， 以90.6%的产率得到1-(2-hydroxyphenyl)-3-(o-tolyl)propan-1-one
  参考文献：
  名称：

  Phenylpropiophenone derivatives as potential anticancer agents: Synthesis, biological evaluation and quantitative structure–activity relationship study

  摘要：

  Series of twelve chalcone and propafenone derivatives has been synthesized and evaluated for anticancer activities against Hela, Fem-X, PC-3, MCF-7, LS174 and K562 cell lines. The 2D-QSAR and 3D-QSAR studies were performed for all compounds with cytotoxic activities against each cancer cell line. Partial least squares (PLS) regression has been applied for selection of the most relevant molecular descriptors and QSAR models building. Predictive potentials of the created 2D-QSAR and 3D-QSAR models for each cell line were compared, by use of leave-one-out cross-validation and external validation, and optimal QSAR models for each cancer cell line were selected. The QSAR studies have selected the most significant molecular descriptors and pharmacophores of the chalcone and propafenone derivatives and proposed structures of novel chalcone and propafenone derivatives with enhanced anticancer activity on the HeLa, Fem-X, PC-3, MCF-7, LS174 and K562 cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.013
• 作为产物：
  描述：

  苯基二乙基氨基甲酸酯 在 lithium diisopropyl amide 、 碘甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (E)-3-(2-methylphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  从氨基甲酸酯到查尔酮：连续的阴离子炸薯条重排，阴离子Si→C烷基重排和Claisen–Schmidt缩合

  摘要：

  开发了一种高效的一锅法，可从苯基二乙基氨基甲酸酯合成各种2'-羟基查耳酮，其特征是连续进行一次Snieckus-Fries重排，阴离子Si→C烷基重排和Claisen-Schmidt缩合。该协议的适用性通过高效合成抗炎天然产物长果皮苷得到了证明。还提供了机制的见解。

  DOI：

  10.1021/acs.orglett.8b02269

文献信息

• 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。
• Palladium-catalyzed stereoselective (3 + 2) cycloaddition of vinylethylene carbonates with cyclic <i>N</i>-sulfonyl ketimines
  作者：Xing Gao、Dongyu Zhu、Feng Jiang、Jianning Liao、Wei Wang、Yongjun Wu、Lufei Zheng、Hongchao Guo

  DOI：10.1039/d1ob00614b

  日期：——

  A diastereoselective (3 + 2) cycloaddition of N-sulfonyl ketimines with vinylethylene carbonates (VECs) in the presence of Pd2dba3·CHCl3 and PPh3 has been developed. The reaction of various substituted VECs and diverse cyclic N-sulfonyl ketimines proceeded smoothly under mild conditions, giving highly functionalized oxazolidine frameworks in good to excellent yields with moderate to good diastereoselectivities

  已经开发了在 Pd 2 dba 3 ·CHCl 3和 PPh 3存在下N-磺酰基酮亚胺与乙烯基碳酸乙烯酯 (VEC)的非对映选择性 (3 + 2) 环加成反应。各种取代的VECs和各种环状N-磺酰基酮亚胺的反应在温和条件下顺利进行，得到高度官能化的恶唑烷骨架，产率良好，非对映选择性适中。使用基于螺缩酮的二膦 SKP 作为手性配体，实现了当前 (3 + 2) 环加成的不对称形式，并且在大多数情况下获得了 > 99% ee 的手性产物。
• Differences in antioxidant potential of chalcones in human serum: In vitro study
  作者：Tamara Janković、Nemanja Turković、Jelena Kotur-Stevuljević、Zorica Vujić、Branka Ivković

  DOI：10.1016/j.cbi.2020.109084

  日期：2020.6

  values. Samples with Ch11 and Ch13 showed significant negative correlation between TAS and TOS (p < 0.05 for both), but in Ch14 sample the negative correlation existed between TAS and PAB (p < 0.05). CONCLUSION Lower value of OS (i.e. better antioxidative potency) was noticed in samples with Ch11-Ch15. Electron-donor effects of substituent groups as a structural part of these chalcones could explain

  引言氧化剂和抗氧化剂之间的不平衡以氧化剂为先导，可能导致损害，被称为氧化应激。酶性或非酶性抗氧化剂（AO）均可减少促氧化剂如DNA，蛋白质和脂质损伤的多种作用。Chalcones（1,3-diaryl-2-propen-1-ones）是在植物中广泛生物合成的开链类黄酮。这项研究的目的是在体外模型中（天然条件下）测试15个查耳酮（Chs）的抗氧化能力，以及外源性氧化应激。材料与方法用0.25 mmol / L叔丁基氢过氧化氢（TBH）在健康个体的血清样品中诱导氧化应激，然后我们监测了各种浓度的查耳酮对氧化应激参数的影响：总抗氧化状态（TAS），总氧化状态（TOS），巯基总浓度（SHG）和氧化前-抗氧化平衡（PAB），以及计算出的氧化前评分，抗氧化评分和氧化评分（OS）。采用非参数重复测量方差分析（Friedman's test），以天然状态和TBH影响比较具有15种不同查耳酮的样品的抗氧化能
• Photorearrangement of phenyl cinnamates under micellar environment
  作者：A.K. Singh、T.S. Raghuraman

  DOI：10.1016/s0040-4039(00)89310-7

  日期：1985.1

  Photolysis of phenyl cinnamates in aqueous SDS medium results in an efficient and high yield synthesis of the corresponding 2′-hydroxychalcones.

  肉桂酸苯基酯在水性SDS介质中的光解作用可有效且高产率地合成相应的2'-羟基查耳酮。
• Microwave assisted synthesis, characterization, molecular docking and pharmacological activities of some new 2′-hydroxychalcone derivatives
  作者：Mohammad Nasir Uddin、Md Nazmul Hassan Knock、Monir Uzzaman、M. Mosharef H. Bhuiyan、A.F.M. Sanaullah、Wahhida Shumi、Hossain Md Sadrul Amin

  DOI：10.1016/j.molstruc.2020.127678

  日期：2020.4

  Abstract Synthesis of six new α, β-unsaturated carbonyl compounds (2′-hydroxychalcones) from 2′-hydroxyacethophenone and aromatic aldehyde derivatives under microwave condition has been described due to their pharmaceutical interest. They were characterized by FTIR, 1H NMR, Mass spectra, micro-analytical data and other physic-chemical properties. Density functional theory (DFT) with B3LYP/6-311 + G

  摘要 6 种新的 α, β-不饱和羰基化合物（2'-羟基查尔酮）在微波条件下由 2'-羟基苯乙酮和芳香醛衍生物合成，由于它们的药学价值，已被描述。它们通过 FTIR、1H NMR、质谱、微量分析数据和其他理化性质进行表征。使用 B3LYP/6-311 + G (d,p) 的密度泛函理论 (DFT) 已用于优化所有合成的查耳酮，这有助于根据实验证据确认提出的化合物的结构。合成的化合物被证明可以抑制微生物活性并显示出良好的抗氧化性能。针对前列腺素 H2 (PGH2) 合酶蛋白 5F19 进行分子对接。