(2E)-1-(4-fluorophenyl)-3-(4-methylphenyl)prop-2-en-1-one | 313236-80-5

• 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: (2E)-1-(4-fluorophenyl)-3-(4-methylphenyl)prop-2-en-1-one
• 英文别名: (E)-1-(4-fluorophenyl)-3-(4-methylphenyl)prop-2-en-1-one；(E)-1-(4-fluorophenyl)-3-(p-tolyl)prop-2-en-1-one；(E)-1-(4-fluorophenyl)-3-p-tolylprop-2-en-1-one；(2E)-1-(4-fluorophenyl)-3-(4-tolyl) prop-2-en-1-one
• CAS: 313236-80-5
• 化学式: C₁₆H₁₃FO
• 分子量: 240.277
• InChiKey: VFACJAJCQBVGDJ-IZZDOVSWSA-N

物化性质

• 沸点：
  373.9±42.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-1-(4-fluorophenyl)-3-(4-methylphenyl)prop-2-en-1-one 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 29.0h， 生成 1-[(E)-1-(4-Fluoro-phenyl)-3-p-tolyl-allyl]-1H-imidazole
  参考文献：
  名称：

  Desideri, Nicoletta; Sestili, Isabella; Artico, Marino, Medicinal Chemistry Research, 1995, vol. 5, # 6, p. 431 - 441

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氟苯乙炔 、 对甲基苯甲醛 在 亚磷酸 作用下， 以 水 为溶剂， 反应 24.0h， 以80%的产率得到(2E)-1-(4-fluorophenyl)-3-(4-methylphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Phosphorous Acid Promoted Hydration–Condensation of Aromatic Alkynes with Aldehydes Affording Chalcones in an Oil/Water Two-Phase System

  摘要：

  A simple and environmentally benign method was developed for the synthesis of chalcones in high to excellent yields by a phosphorous acid promoted alkyne-aldehyde hydration-condensation in an oil/water two-phase system. The method is the first efficient protocol for the preparation of chalcones that is mediated by a simple BrOnsted acid in a two-phase system.

  DOI：

  10.1055/s-0035-1560832

文献信息

• Asymmetric Conjugate Addition of Organoboron Reagents to Common Enones Using Copper Catalysts
  作者：Chunlin Wu、Guizhou Yue、Christian Duc-Trieu Nielsen、Kai Xu、Hajime Hirao、Jianrong (Steve) Zhou

  DOI：10.1021/jacs.5b11441

  日期：2016.1.27

  Copper complexes of phosphoramidites efficiently catalyzed asymmetric addition of arylboron reagents to acyclic enones. Importantly, rare 1,4-insertion of arylcopper(I) was identified which led directly to O-bound copper enolates. The new mechanism is fundamentally different from classical oxidative addition/reductive elimination of organocopper(I) on enones.

  亚磷酰胺的铜配合物有效地催化芳基硼试剂向无环烯酮的不对称加成。重要的是，鉴定了稀有的芳基铜（I）的 1,4-插入，这直接导致了与 O 结合的铜烯醇化物。新机制与传统的有机铜（I）在烯酮上的氧化加成/还原消除有着根本的不同。
• Alkylation of Indoles with α,β‐Unsaturated Ketones using Alumina in Hexanes
  作者：Xiong Zhang、Ebenezer Jones‐Mensah、Jackson Deobald、Jakob Magolan

  DOI：10.1002/adsc.201901037

  日期：2019.12.17

  We evaluated the influence of solvent on the alumina‐promoted C3‐alkylation of indoles with α,β‐unsaturated ketones. We found that lipophilic solvents were generally superior to hydrophilic ones with hexanes offering the 3‐alkyl indole products in high yields. Thus, we demonstrate an inexpensive and procedurally simple new process that pairs acidic alumina with hexanes to achieve this important Michael

  我们评估了溶剂对带有α，β-不饱和酮的吲哚的氧化铝促进的C3-烷基化的影响。我们发现亲脂性溶剂通常优于亲水性溶剂，而己烷可提供高收率的3-烷基吲哚产物。因此，我们证明了一种廉价且程序简单的新方法，该方法将酸性氧化铝与己烷配对以实现这一重要的迈克尔烷基化反应。底物范围包括二十四个实例，反应产率为61％至96％。
• Domino-Fluorination–Protodefluorination Enables Decarboxylative Cross-Coupling of α-Oxocarboxylic Acids with Styrene via Photoredox Catalysis
  作者：Muliang Zhang、Junwei Xi、Rehanguli Ruzi、Nan Li、Zhongkai Wu、Weipeng Li、Chengjian Zhu

  DOI：10.1021/acs.joc.7b01054

  日期：2017.9.15

  a carbon-centered radical intermediate, which will overcome side reactions during the styrene radical functionalization process. Experimental studies have provided evidence indicating a domino-fluorination–protodefluorination pathway with α-keto acid initiating the photoredox cycle. The present catalytic protocol also affords a novel approach for the construction of α,β-unsaturated ketones under mild

  通过光氧化还原催化，已经开发出α-酮酸与苯乙烯的多米诺氟化-原脱氟脱羧交叉偶联。该策略的关键部分是通过捕获以碳为中心的自由基中间体形成碳-氟（C-F）键，这将克服苯乙烯自由基官能化过程中的副反应。实验研究提供了证据，表明具有α-酮酸的多米诺氟化-原脱氟途径可引发光氧化还原循环。本催化方案还提供了在温和条件下构建α，β-不饱和酮的新方法。
• Syntheses and biological activity of chalcones-imidazole derivatives
  作者：Yu-Ting Liu、Xiao-Ming Sun、Da-Wei Yin、Fang Yuan

  DOI：10.1007/s11164-012-0665-z

  日期：2013.3

  A number of novel 13-membered chalcone-imidazole derivatives were prepared and have been synthesized and characterized by IR, 1H NMR, 13C NMR and elemental analysis, the results conformed well to expected structures. Substituted acetophenones and benzaldehydes were condensed using the Claisen–Schmidt base-catalyzed aldol condensation. Methyl on the aromatic ring of chalcones was brominated by NBS, and then the resulting mixture was reacted with imidazole to get the target compound. Several chalcones showed in vitro antibacterial activity against Gram-bacterial. The results showed that these are potential antibacterial compounds.

  制备了一系列新型的13元查尔酮-咪唑衍生物，并通过IR、1H NMR、13C NMR和元素分析进行了合成和表征，结果与预期结构吻合良好。使用Claisen-Schmidt碱催化醛缩反应，将取代的乙酰苯和苯甲醛缩合。查尔酮芳香环上的甲基通过NBS进行溴化，然后将所得混合物与咪唑反应，得到目标化合物。几种查尔酮显示出对革兰氏细菌的体外抗菌活性。结果表明，这些化合物具有潜在的抗菌活性。
• Trimethylsilyl-1,3,4-oxadiazoles—new useful synthons for the synthesis of various 2,5-disubstituted-1,3,4-oxadiazoles
  作者：Evgenij V. Zarudnitskii、Igor I. Pervak、Anatolij S. Merkulov、Aleksandr A. Yurchenko、Andrej A. Tolmachev

  DOI：10.1016/j.tet.2008.08.040

  日期：2008.11

  The reactivity of 2-aryl-5-trimethylsilyl-1,3,4-oxadiazoles toward different types of electrophiles was investigated. These silanes readily react with chlorine, bromine, aliphatic acyl chlorides, 2-nitrobenzenesulfenyl chloride, and some reactive isocyanates affording the corresponding substituted 1,3,4-oxadiazoles. The reactions with carbonyl compounds proceed only in the presence of F− anions.

  研究了2-芳基-5-三甲基甲硅烷基-1,3,4-恶二唑对不同类型亲电试剂的反应性。这些硅烷容易与氯，溴，脂肪族酰氯，2-硝基苯磺酰氯和一些反应性异氰酸酯反应，得到相应的取代的1,3,4-恶二唑。与羰基化合物反应仅进行在F的存在-的阴离子。