3-(2,6-二氯苯基)-1-(2-羟基苯基)丙-2-烯-1-酮 | 73110-44-8

• 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
• 中文名称: 3-(2,6-二氯苯基)-1-(2-羟基苯基)丙-2-烯-1-酮
• 英文名称: 3-(2,6-dichlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• 英文别名: 2,6-Dichloro-2'-hydroxychalcone
• CAS: 73110-44-8；88701-85-3
• 化学式: C₁₅H₁₀Cl₂O₂
• 分子量: 293.149
• InChiKey: DBQYHWPRRQKNKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  455.8±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：

  3-(2,6-二氯苯基)-1-(2-羟基苯基)丙-2-烯-1-酮 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成 2-(2,4-dichlorophenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Design, synthesis and biological activity of flavonoid derivatives as selective agonists for neuromedin U 2 receptor

  摘要：

  Central neuromedin U 2 receptor (NMU2R) plays important roles in the regulation of food intake and body weight. Identification of NMU2R agonists may lead to the development of pharmaceutical agents to treat obesity. Based on the structure of rutin, a typical flavonoid and one of the NMU2R agonists we previously identified from an in-house made natural product library, 30 flavonoid derivatives have been synthesized and screened on a cell-based reporter gene assay. A number of compounds were found to be selective and highly potent to NMU2R. For example, the EC50 value of compound NRA 4 is very close to that of NMU, the endogenous peptide ligand of NMU2R. Structure-activity relationship analysis revealed that a 3-hydroxyl group in ring C and a 2'-fluoride group in ring B were essential for this class of compounds to be active against NMU2R. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.08.038
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 2,6-二氯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-(2,6-二氯苯基)-1-(2-羟基苯基)丙-2-烯-1-酮
  参考文献：
  名称：

  X 射线表征、Hirshfeld 表面分析、DFT 计算、二氯苯基取代的 3-羟基色农的体外和硅脂氧化酶抑制 (LOX) 研究

  摘要：

  这项工作报告了三种二氯苯基取代的 3-羟基-chromen-4-one 衍生物的合成和 X 射线表征，即2-(2,4-dichlorophenyl)-3-hydroxy-4 H -chromen-4-one ( 1 ), 2-(2,3-二氯苯基)-3-羟基-4 H -chromen-4-one ( 2 ), 和 2-(2,6-二氯苯基)-3-羟基-4 H -chromen-4 -一 ( 3）。由于 Cl 取代基对苯基环和色酮环之间的二面角影响很大，这三种异构体的固态结构大不相同。已经使用 Hirshfeld 表面分析并通过计算它们的相互作用能和不同的贡献（静电、极化、色散和排斥）来研究不同的组件和合成子。此外，只有一种异构体形成定向卤素键相互作用（C-Cl⋯O），已使用 MEP 表面计算进行分析，并使用 QTAIM 和 NCIplot 指数计算方法的组合进行表征。还分析了根据取代形成卤素键

  DOI：

  10.1039/d1nj04340d

文献信息

• Eco-friendly polyethylene glycol promoted Michael addition reactions of α,β-unsaturated carbonyl compounds
  作者：Dalip Kumar、Gautam Patel、Braja G. Mishra、Rajender S. Varma

  DOI：10.1016/j.tetlet.2008.09.116

  日期：2008.12

  Intra- and inter-nucleophilic addition reactions of different α,β-unsaturated carbonyl compounds were found to be highly effective without any additives in PEG-400 as a recyclable reaction medium under neutral conditions.

  发现在中性条件下，不同的α，β-不饱和羰基化合物在亲核内和间的加成反应非常有效，而PEG-400中没有任何添加剂可作为可循环的反应介质。
• Ionic liquid catalyzed expeditious synthesis of 2-aryl-2,3-dihydroquinolin-4(1<i>H</i>)-ones and 2-aryl-2,3-dihydro-4<i>H</i>-chromen-4-ones under microwave irradiation
  作者：Dalip Kumar、Gautam Patel、Anil Kumar、Ram K. Roy

  DOI：10.1002/jhet.123

  日期：2009.7

  A facile and convenient synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-one and 2-aryl-2,3-dihydro-4H-chromen-4-one has been described using ionic liquid catalyzed intramolecular cyclization of the corresponding 2′-aminochalcones and 2′-hydroxychalcones, respectively. The rapid and fairly general protocol affords product in good yield. Ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate, was

  已经描述了使用离子液体催化的分子内分子方便且方便地合成2-芳基-2,3-二氢喹啉-4（1 H）-one和2-芳基-2,3-二氢-4 H-铬烯-4-酮的方法。分别将相应的2'-氨基查耳酮和2'-羟基查耳酮环化。快速且通用的协议可提供高产量的产品。回收离子液体四氟硼酸1-丁基-3-甲基咪唑鎓并重新使用，而不会降低其效率。J.杂环化​​学。（2009）
• Oxidative Cyclization Reactions Catalyzed by Designed Transition-Metal Complexes: A New Strategy for the Synthesis of Flavone, Quinolone, and Benzofuran Derivatives
  作者：Kaushik Ghosh、Naseem Ahmed、Apurva Singh、Sain Singh

  DOI：10.1055/s-0042-1751489

  日期：2023.12

  An efficient and convenient synthetic protocol is reported for the synthesis of 2-phenyl-4H-chromen-4-one, 2-phenylquinolin-4(1H)-one, and 11H-benzofuro[3,2-b]chromen-11-one derivatives from 2′-hydroxychalcones, 2′-aminochalcones, and 3-hydroxyflavones, respectively, using transition-metal catalysts and TEMPO as an oxidizing agent. This catalytic heterocyclization approach involves in situ free-radical

  报道了一种有效且方便的合成方案，用于合成 2-苯基-4 H -chromen-4-one、2-苯基喹啉-4(1 H )-one 和 11 H-苯并呋喃[3,2- b ]chromen使用过渡金属催化剂和 TEMPO 作为氧化剂，分别从 2'-羟基查尔酮、2'-氨基查尔酮和 3-羟基黄酮生成 -11-酮衍生物。这种催化杂环化方法涉及原位自由基生成，通过 EPR 光谱研究和 H 2 O 2检测到苯氧基自由基。成立了。该方法具有许多优点，例如原子经济性高、合成危险性小、溶剂和助剂良性、易于操作、底物范围更广以及良好至优异的产物收率。
• Access to Chromenopyrrole via Tandem [3 + 2] Cycloaddition and Intramolecular C–O Coupling
  作者：Bubul Das、Nikita Chakraborty、Hirendra Nath Dhara、Pratip Bhattacharyya、Bhisma K. Patel

  DOI：10.1021/acs.joc.3c02479

  日期：2024.1.19

  A mild and concise method for the synthesis of chromenopyrrole from 2′-hydroxychalcone is devised. The reaction proceeds via an initial [3 + 2] cycloaddition on the C═C bond of 2′-hydroxychalcone and 1,3-dipolarophile, generated in situ by the reaction of ethyl isocyanoacetate and AgOAc. This is then followed by an intramolecular C–O bond formation with the −OH group and C5–H of the in situ generated

  设计了一种温和、简洁的从 2'-羟基查尔酮合成色吡咯的方法。该反应通过 2'-羟基查耳酮和 1,3-亲偶极试剂的 C=C 键上的初始 [3 + 2] 环加成进行，该键是由异氰基乙酸乙酯和 AgOAc 反应原位生成的。然后与原位生成的吡咯的 -OH 基团和 C5-H 形成分子内 C-O 键，形成色并吡咯。
• An unexpected rearrangement-hydration reaction sequence of 2H-chromenes to dihydrochalcones under catalysis of HAuCl4
  作者：Gourhari Maiti、Utpal Kayal、Rajiv Karmakar、Rudraksha N. Bhattacharya

  DOI：10.1016/j.tetlet.2012.08.117

  日期：2012.11

  2-Aryl-2H-chromenes in aqueous DCM medium under catalysis of HAuCl4 are converted into 3-(2-hydroxyaryl)-1-arylpropan-1-ones through hydration-rearrangement reaction sequence in very good yield. The key step probably involves the [1,5] hydride shift followed by the hydrolysis under the reaction condition. The notable advantages of this method are operational simplicity and ease of isolation of products and also provide a pathway to convert the chalcone into DHCs with the transposition of carbonyl group. (C) 2012 Elsevier Ltd. All rights reserved.