2'-hydroxy-5'-methylchalcone

• 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: 2'-hydroxy-5'-methylchalcone
• 英文别名: 2'-Hydroxy-5'-methyl-chalkon；5'-Methyl-2'-hydroxy-chalkon；2'-Hydroxy-5'-methylchalcon；3-phenyl-1-(2'-hydroxy-5'-methylphenyl)-2-propen-1-one；1-(2-Hydroxy-5-methyl-phenyl)-3-phenyl-prop-2-en-1-one；1-(2-hydroxy-5-methylphenyl)-3-phenylprop-2-en-1-one
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: BPAVQKLQOSHOPN-UHFFFAOYSA-N

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：

  2'-hydroxy-5'-methylchalcone 在 溴 、 溶剂黄146 作用下， 生成 2'-hydroxy-5'-methylchalkone dibromide
  参考文献：
  名称：

  Agrawal, Nitin N.; Soni, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007, vol. 46, # 3, p. 532 - 534

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酸对甲酚酯 在 sodium hydroxide 、 三氯化铝 作用下， 以 乙醇 为溶剂， 反应 48.75h， 生成 2'-hydroxy-5'-methylchalcone
  参考文献：
  名称：

  6-Methylflavanone, a more efficacious positive allosteric modulator of γ-aminobutyric acid (GABA) action at human recombinant α2β2γ2L than at α1β2γ2L and α1β2 GABAA receptors expressed in Xenopus oocytes

  摘要：

  6-Methylflavanone acted as a positive allosteric modulator of gamma-aminobutyric acid (GABA) responses at human recombinant alpha(1)beta(2)gamma(2L), alpha(1)beta(2)gamma(2L) and alpha(1)beta(2) GABA(A) receptors expressed in Xenopus laevis oocytes. It was essentially inactive at rho(1) GABA(C) receptors.The EC50 values for 6-methylflavanone for the positive modulation of the EC10-20 GABA responses were 22 mu M, 10 mu M and 6 mu M and the maximum potentiations were 120%, 417% and 130% at a alpha(1)beta(2)gamma(2L), alpha(1)beta(2)gamma(2L) and alpha(1)beta(2) GABA(A) receptors respectively.Thus 6-methylflavanone was much more efficacious as a positive modulator at alpha(1)beta(2)gamma(2L) than at alpha(1)beta(2)gamma(2L) and alpha(1)beta(2) GABA(A) receptors. This may be significant since diazepam-induced anxiolysis is considered to be mediated via alpha(2)-containing GABA(A) receptors, while sedation is thought to be mediated via alpha(1)-containing GABA(A) receptors.We have previously reported that 6-methylflavone (1-100 mu M) produced positive allosteric modulation at a alpha(1)beta(2)gamma(2L) and alpha(1)beta(2) GABA(A) receptors with no significant difference between the enhancement seen at either receptor subtype. In the present study, 6-methylflavone was tested at alpha(2)beta(2)gamma(2L) GABA(A) receptors and found to maximally potentiate the EC10-20 GABA response by 183 +/- 39% which is similar to that previously observed for 6-methylflavone at alpha(1)beta(2)gamma(2L) GABA(A) receptors. Thus, 6-methylflavone did not show a preference for alpha(2)beta(2)gamma(2L) over alpha(1)beta(1)gamma(2L) GABA(A) receptors in terms of efficacy.Compared to 6-methylflavone, 6-methylflavanone is more efficacious as a positive allosteric modulator at alpha(2)beta(2)gamma(2L) GABA(A) receptors, and less efficacious at alpha(1)beta(2)gamma(2L) GABA(A) receptors. This may represent a relatively unique type of selectivity for positive modulators of GABA-A receptor subtypes based on efficacy as distinct from potency.As was previously shown for 6-methylflavone at a alpha(1)beta(2)gamma(2L) GABA(A) receptors, the positive modulation of GABA responses at alpha(1)beta(2)gamma(2L) and alpha(2)beta(2)gamma(2L) GABA(A) receptors by 6-methylflavanone was insensitive to antagonism by flumazenil, indicating that this action is not mediated via "high-affinity" benzodiazepine sites. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejphar.2005.02.034

文献信息

• Ruthenium(II)-Catalyzed Synthesis of Spirobenzofuranones by a Decarbonylative Annulation Reaction
  作者：Partha P. Kaishap、Gauri Duarah、Bipul Sarma、Dipak Chetia、Sanjib Gogoi

  DOI：10.1002/anie.201710049

  日期：2018.1.8

  activation of six‐membered compounds is reported. The Ru‐catalyzed reaction of 3‐hydroxy‐2‐phenyl‐chromones with alkynes works most efficiently in the presence of the ligand PPh3 to provide spiro‐indenebenzofuranones. Unlike previously reported metal‐catalyzed decarbonylative annulation reactions, in the present decarbonylative annulation reaction, the annulation occurs before extrusion of carbon monoxide

  据报道，炔烃通过六元化合物的C / H / C-C活化而首次脱羰基插入。在配体PPh 3存在下，Ru-催化的3-羟基-2-苯基色酮与炔烃的反应最有效，可提供螺茚二苯并呋喃酮。与以前报道的金属催化的脱羰环化反应不同，在本脱羰环化反应中，环化发生在一氧化碳挤出之前。
• Biocatalytic green alternative to existing hazardous reaction media: synthesis of chalcone and flavone derivatives <i>via</i> the Claisen–Schmidt reaction at room temperature
  作者：Kashyap J. Tamuli、Ranjan K. Sahoo、Manobjyoti Bordoloi

  DOI：10.1039/d0nj03839c

  日期：——

  Hook. F. peel ash (MCPA) are used as catalysts to promote an inexpensive, efficient and eco-friendly carbon–carbon bond forming crossed aldol reaction at room temperature in solvent free conditions. Furthermore, the resulting products were subjected to reactions with these promoters in an oxygen atmosphere and led to the formation of novel flavone derivatives. Moreover, the used catalysts were properly

  由于全球废料数量的增加，将废料或次级副产品转化为用于各种应用的增值产品引起了人们的极大兴趣。在此，两种新颖的农业食品废品Musa sp。``马尔堡''果皮灰（MMPA）和Musa Champa霍特 前钩。F.果皮灰（MCPA）用作催化剂，可促进在室温下无溶剂条件下廉价，高效且生态友好的碳-碳键形成交叉羟醛反应。此外，在氧气气氛中使所得产物与这些促进剂反应，并导致形成新的黄酮衍生物。此外，使用不同的复杂分析技术，例如傅立叶变换红外光谱（FT-IR），X射线衍射法（XRD），Brunauer-Emmett-Teller分析（BET），拉曼光谱，扫描电子显微镜，对用过的催化剂进行了适当的表征。能量色散X射线光谱（SEM-EDS），过渡电子显微镜（TEM），X射线光电子能谱（XPS）和热重分析（TGA）以及使用原子吸收光谱和离子色谱法的元素检测。这两种方法均不含金属，并且不含任何额外的添加剂，助催
• Selective Synthesis of 3,4-Dihydrocoumarins and Chalcones from Substituted Aryl Cinnamic Esters
  作者：Jae-Ho Jeon、Deok-Mo Yang、Jong-Gab Jun

  DOI：10.5012/bkcs.2011.32.1.65

  日期：2011.1.20

  Coumarins are ubiquitous in plant kingdom and have been used as antitumor, antifungals, anticoagulants, insecticides. Chalcones are also widespread in plant kingdom and have been known to possess diverse biological activities; antibacterial, antifungal, antitumor and anti-inflammatory, etc. As they are considered as important natural products, numerous synthetic approaches have been reported up to the present. We devise a new selective method of preparing dihydrocoumarins and chalcones from aryl cinnamates by the selection of reagents. Dihydrocoumarin derivatives were prepared selectively by using intramolecular cyclization catalyzed by p-toluene sulfonic acid. Also, chalcones were prepared by Fries-rearrangement catalyzed by $TiCl_4$. This method can be used for preparing various coumarin & chalcone compounds.

  香豆素广泛存在于植物王国中，并已被用作抗癌剂、抗真菌剂、抗凝血剂和杀虫剂。查尔酮也在植物王国中广泛分布，并且已知具有多种生物活性，包括抗菌、抗真菌、抗癌和抗炎等。由于它们被认为是重要的天然产物，迄今为止已经报道了许多合成方法。我们设计了一种新的选择性方法，通过选择试剂，从芳基肉桂酸制备二氢香豆素和查尔酮。通过使用对甲苯磺酸催化的分子内环化反应，选择性地制备了二氢香豆素衍生物。此外，还通过三氯化钛催化的Fries重排反应制备了查尔酮。这种方法可以用于制备各种香豆素和查尔酮化合物。
• Asymmetric Ion-Pairing Catalysis of the Reversible Cyclization of 2′-Hydroxychalcone to Flavanone: Asymmetric Catalysis of an Equilibrating Reaction
  作者：Lukas Hintermann、Claudia Dittmer

  DOI：10.1002/ejoc.201200838

  日期：2012.10

  The asymmetric catalytic cyclization of the simple 2′-hydroxychalcone (1) to flavanone (2), a model for the chalcone isomerase reaction, has been realized as a catalytic asymmetric ion-pairing process with chiral quaternary ammonium salts (e.g., 9-anthracenylmethlycinchoninium chloride; 9-Am-CN-Cl) and NaH as small-molecule co-catalyst. In toluene/CHCl3 solution, the process reaches an intrinsic enantioselectivity

  简单的 2'-羟基查尔酮 (1) 到黄烷酮 (2) 的不对称催化环化是查尔酮异构酶反应的模型，已被实现为手性季铵盐（例如，9-蒽基甲基辛可宁鎓）的催化不对称离子配对过程氯化物；9-Am-CN-Cl) 和 NaH 作为小分子助催化剂。在甲苯/CHCl3 溶液中，该过程达到了高达 S = 14.4 (er = 93.5:6.5) 的固有对映选择性。可逆反应分两步进行：快速初始反应接近 KR/S = 4.5 的准平衡，然后是接近 Krac = 9 的第二个缓慢外消旋阶段。提出了可逆性。氘从共溶剂 CDCl3 转移到产物 2 以及由 2 和 1 形成的迈克尔共轭物的分离证明了黄烷酮烯醇化物离子对的中介作用。动力学模型显示出与实验观察到的物种浓度和对映体过量 2 的独特的时间依赖性演化非常一致。该反应是查尔酮异构酶酶促反应的化学模型。此外，它是研究接近平衡的可逆不对称催化剂的特征行为的理想模型。该反
• Chiral Hydroxytetraphenylene–Boron Complex Catalyzed Asymmetric Diels–Alder Cycloaddition of 2′-Hydroxychalcones
  作者：Guo-Li Chai、Yan Qiao、Ping Zhang、Rong Guo、Juan Wang、Junbiao Chang

  DOI：10.1021/acs.orglett.0c02978

  日期：2020.10.16

  15-Cl2-DHTP–boron complex catalyst for the asymmetric Diels–Alder cycloaddition of 2′-hydroxychalcones and dienes was developed and tested. The resulting cyclohexenes with three chiral centers were obtained in high yields (up to 98%) with excellent stereoselectivities (up to >20:1 endo/exo, >99% ee). This catalytic system features high efficiency, broad substrate scopes, and mild reaction conditions. In

  （小号）-2,15-CL 2 -DHTP -硼为2'-hydroxychalcones和二烯不对称狄尔斯-阿尔德环加成配合物催化剂进行开发和测试。得到的具有三个手性中心的环己烯以高收率（高达98％）和优异的立体选择性（高达> 20：1 end / exo，> 99％ee）获得。该催化系统具有高效，广泛的底物范围和温和的反应条件的特点。另外，进行了DFT研究以解释不对称诱导的立体化学过程。