3-(3,4-difluorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde | 881667-32-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(3,4-difluorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 3-(3,4-difluorophenyl)-1-phenylpyrazole-4-carbaldehyde
• CAS: 881667-32-9
• 化学式: C₁₆H₁₀F₂N₂O
• 分子量: 284.265
• InChiKey: UXBFMTHBXUXOBC-UHFFFAOYSA-N

物化性质

• 沸点：
  441.8±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3,4-difluorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde 在 potassium hydroxide 、 copper dichloride 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 3-chloro-2-(3-(3,4-difluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-4H-chromen-4-one
  参考文献：
  名称：

  Gaikar, Rajendra B.; Gadhave, Anil G.; Karale, Bhausaheb K., Indian Journal of Heterocyclic Chemistry, 2011, vol. 20, # 4, p. 385 - 388

  摘要：

  DOI：
• 作为产物：
  描述：

  3',4'-二氟苯乙酮 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 3-(3,4-difluorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  吡唑-咪唑并[1,2-α]吡啶分子缀合物的新文库：合成，抗菌活性和分子对接研究。

  摘要：

  设计并通过一锅三组分串联反应合成了新型吡唑-咪唑并[1,2-α]吡啶骨架。通过光谱技术（NMR，IR和HRMS）证实了合成的缀合物的结构。对耐甲氧西林金黄色葡萄球菌和大肠杆菌，鼠伤寒沙门氏菌，肺炎克雷伯菌和铜绿假单胞菌等正常菌株的十二种合成分子（7a，8a-k）的体外抗菌评估建立了有效的抗菌剂8b，8d，8e，8h和8i。与标准药物环丙沙星相比，具有最低最低杀菌浓度的杀菌剂。

  DOI：

  10.1111/cbdd.13632

文献信息

• One pot synthesis of thiazolo[2,3-b]dihydropyrimidinone possessing pyrazole moiety and evaluation of their anti-inflammatory and antimicrobial activities
  作者：Shivapura Viveka、Dinesha、Gundibasappa Karikannar Nagaraja、Prasanna Shama、Guru Basavarajaswamy、K. Poornachandra Rao、Marikunte Yanjarappa Sreenivasa

  DOI：10.1007/s00044-017-2058-8

  日期：2018.1

  3-b]dihydropyrimidinone derivatives were synthesized as dual anti-inflammatory and antimicrobial agents. Among the compounds studied, 3-fluoro-4-methylphenyl analogues (3a, 3e, and 3i) are considered to be promising leads for novel anti-inflammatory agents compared with the standard drug. The superior antimicrobial property of the compounds 3a, 3b, and 3d indicates that 3-(3,4-dichlorophenyl)-1-phenyl-1H-pyrazole

  合成了一系列吡唑结合的噻唑并[2,3- b ]二氢嘧啶酮衍生物作为抗炎和抗菌药。在研究的化合物中，与标准药物相比，3-氟-4-甲基苯基类似物（3a，3e和3i）被认为是新型抗炎药的有前途的线索。化合物3a，3b和3d的优异抗菌性能表明3-（3,4-二氯苯基）-1-苯基-1 H-吡唑取代是高活性的有利部位。进行了分子对接研究，以预测这些化合物与COX-2同工酶的假设结合模式。本研究的结果表明，噻唑并[2,3- b ]二氢嘧啶酮衍生物上的1,3-二芳基吡唑取代可能潜在地构成一类具有抗菌特性的新型消炎药，并且可能是一种有趣的药物设计方法。新的选择性COX-2抑制剂。
• Ionic Liquid: An Efficient and Facile Catalyst for the Synthesis of Trisubstituted Imidazole Derivatives via Multi-Component Pathway Using Green Techniques
  作者：Gopinath D. Shirole、Sharad N. Shelke

  DOI：10.2174/1570178614666161114165113

  日期：2017.1.3

  Background: A green path for the synthesis of 3-aryl-1-phenyl-4-(4,5-diphenyl-1H-imidazol-2-yl)-1Hpyrazole derivatives using [BMIM][BF4] as a catalyst and green methods such as ultrasound and microwave irradiation is discussed in this paper. The titled compounds were obtained by the multi-component condensation of various 3-aryl-1-phenyl-1H-pyrazole-4-carboxaldehydes, benzil and ammonium acetate. One pot synthesis, simple reaction conditions and quantitative yields illustrate the utility of this green approach. Methods: Conventional Reflux Condition: A mixture of 3-aryl-1-phenyl-1H-pyrazole-4-carboxaldehyde 1 (1 mmol), benzil 2 (1 mmol), ammonium acetate 3 (2 mmol) and catalytic amount of [BMIM][BF4] (15 mmol %) was placed in a round bottom flask containing 10 mL of ethanol. The reaction mixture was refluxed for completion. The course of the reaction was monitored by thin layer chromatography. After completion of the reaction, the mixture was poured over crushed ice. Solid imidazole thus obtained was separated by filtration, dried well, and recrystallized by ethanol. Ultrasound Irradiation Method: A mixture of 3-aryl-1-phenyl-1H-pyrazole-4-carboxaldehyde 1 (1 mmol), benzil 2 (1 mmol), ammonium acetate 3 (2 mmol) and catalytic amount of [BMIM][BF4] (15 mmol %) was placed in a round bottom flask containing 10 mL of ethanol. The round bottom flask was placed in an US bath at 50ºC for 80-90 min. The course of the reaction was monitored by thin layer chromatography. After completion of the reaction, the mixture was poured into crushed ice, solid imidazoles thus obtained were separated by filtration, dried well, and recrystallized by ethanol. Microwave Irradiation Method: A 10 mL round bottom flask was charged with 3-aryl-1-phenyl- 1H-pyrazole-4-carboxaldehyde 1 (1 mmol), benzil 2 (1 mmol), ammonium acetate 3 (2 mmol) and catalytic amount of [BMIM] [BF4] (15 mmol %), and placed under MW irradiation at 240 watts for 7-9 min. The course of the reaction was monitored by thin layer chromatography. After completion of the reaction, the mixture was poured over crushed ice, the solid imidazole thus obtained was separated by filtration, dried well, and recrystallized by ethanol. Results: The 3-aryl-1-phenyl-4-(4,5-diphenyl-1H-imidazol-2-yl)-1H-pyrazole derivatives 4a-i (Scheme 1, Table 2) were synthesized by using [BMIM] [BF4] as a catalyst with good yields under reflux in ethanol (68-70%), US irradiation in ethanol (76-80%) and MW irradiation (80-86%) without solvent. All these methods provided good results with IL [BMIM][BF4]. However, the MW and US irradiation methods give good yield in a short period of time with 3-aryl-1-phenyl-1H-pyrazole-4-carboxaldehyde 1 containing a variety of substituents, whereas the conventional reflux condition gives lower yields and takes longer time as compared with MW and US irradiation. The structures of the synthesized compounds have been confirmed on the basis of spectroscopic techniques such as FTIR, HRMS, LCMS, 1H and 13C NMR. Conclusion: In conclusion, we have synthesized differently substituted imidazoles using [BMIM][BF4] as a catalyst under MW and US irradiation via MC condensation strategy. Under the conventional reflux conditions, we get a lower yield in a longer time, while US and MW assisted synthesis gave better results. Comparatively IL [BMIM][BF4] with US and MW irradiation protocol provides several advantages such as improved reaction speed, shorter reaction times, superior yields and a significant contribution towards sustainability.

  背景：本文讨论了使用[BMIM][BF4]作为催化剂，以及超声波和微波辐射等绿色方法合成3-芳基-1-苯基-4-(4,5-二苯基-1H-咪唑-2-基)-1H-吡唑衍生物的绿色途径。所述化合物通过各种3-芳基-1-苯基-1H-吡唑-4-醛、苯基和醋酸铵的多组分缩合获得。一锅合成、简单的反应条件和定量产率展示了这种绿色方法的实用性。 方法：常规回流条件：将3-芳基-1-苯基-1H-吡唑-4-醛1（1 mmol）、苯基2（1 mmol）、醋酸铵3（2 mmol）和催化量的[BMIM][BF4]（15 mmol%）混合，放入含10 mL乙醇的圆底烧瓶中。反应混合物回流至反应完成。通过薄层色谱监测反应进程。反应完成后，将混合物倒入碎冰中。通过过滤分离得到的固体咪唑，充分干燥，并用乙醇重结晶。 超声辐射法：将3-芳基-1-苯基-1H-吡唑-4-醛1（1 mmol）、苯基2（1 mmol）、醋酸铵3（2 mmol）和催化量的[BMIM][BF4]（15 mmol%）混合，放入含10 mL乙醇的圆底烧瓶中。圆底烧瓶放入50ºC的超声波浴中80-90分钟。通过薄层色谱监测反应进程。反应完成后，将混合物倒入碎冰中，分离得到的固体咪唑，通过过滤、充分干燥并用乙醇重结晶。 微波辐射法：将3-芳基-1-苯基-1H-吡唑-4-醛1（1 mmol）、苯基2（1 mmol）、醋酸铵3（2 mmol）和催化量的[BMIM] [BF4]（15 mmol%）放入10 mL的圆底烧瓶中，在240瓦的微波辐射下加热7-9分钟。通过薄层色谱监测反应进程。反应完成后，将混合物倒入碎冰中，分离得到的固体咪唑，通过过滤、充分干燥并用乙醇重结晶。 结果：使用[BMIM][BF4]作为催化剂，在乙醇回流（68-70%）、乙醇的超声波照射（76-80%）和微波照射（80-86%）下以良好的产率合成了3-芳基-1-苯基-4-(4,5-二苯基-1H-咪唑-2-基)-1H-吡唑衍生物4a-i（方案1，表2）。所有这些方法在使用IL [BMIM][BF4]时都取得了良好的结果。然而，微波和超声波辐射法在短时间内给予了良好的产率，同样的反应所用的3-芳基-1-苯基-1H-吡唑-4-醛1含有多种取代基，而传统回流条件给出的产率较低且时间较长。合成化合物的结构通过FTIR、HRMS、LCMS、1H和13C NMR等光谱技术得到确认。 结论：总之，我们采用[BMIM][BF4]作为催化剂，通过微波和超声辐射合成了不同取代基的咪唑，采用MC缩合策略。在常规回流条件下，我们获得较低的产率所需的时间较长，而超声和微波辅助合成则取得了更好的结果。比较而言，使用[BMIM][BF4]与超声和微波辐射方案提供了多种优势，如提高反应速度、缩短反应时间、优越的产率以及对可持续性的显著贡献。
• Design, synthesis, anticonvulsant and analgesic studies of new pyrazole analogues: a Knoevenagel reaction approach
  作者：Shivapura Viveka、Dinesha Dinesha、Prasanna Shama、Shivalingegowda Naveen、Neratur Krishnappagowda Lokanath、Gundibasappa Karikannar Nagaraja

  DOI：10.1039/c5ra17391d

  日期：——

  with substituted thiazolidine, pyrazolone, thiazolo[3,2-a]pyrimidine, Meldrum's acid and barbituric acid yielded a variety of heterocycles bearing the pyrazole moiety. The newly synthesized compounds were characterized by elemental and spectroscopic analysis; in addition, the structure of compound 1a has been elucidated by single crystal X-ray diffraction technique. The synthesized molecules were evaluated

  本工作涉及从3-（3,4-二卤苯基）-1-苯基-1 H-吡唑-4-甲醛开始的许多新化合物的设计和合成。通过采用Knoevenagel缩合反应来合成化合物，以满足抗惊厥和镇痛活性所需的结构先决条件。3-（3,4-二卤代苯基）-1-苯基-1 H-吡唑-4-甲醛与取代的噻唑烷，吡唑啉酮，噻唑并[3,2- a ]嘧啶，梅德鲁姆酸和巴比妥酸反应生成多种带有吡唑部分的杂环。通过元素分析和光谱分析对新合成的化合物进行了表征。另外，化合物1a的结构已经通过单晶X射线衍射技术阐明了这一点。使用最大电休克发作（MES）测试评估合成的分子的体内抗惊厥活性，同时通过甩尾法研究其镇痛活性。此外，使用旋转脚架毒性法研究所选化合物的毒性特征。在合成的化合物中，1a，4a和7a具有有效的抗惊厥活性，1b，5a，5b，7a和7b表现出最高的镇痛活性，没有任何毒性。还努力建立被测化合物之间的构效关系。
• Synthesis of new pyrazole derivatives via multicomponent reaction and evaluation of their antimicrobial and antioxidant activities
  作者：Shivapura Viveka、Dinesha、Leelavathi Narayana Madhu、Gundibasappa Karikannar Nagaraja

  DOI：10.1007/s00706-015-1428-5

  日期：2015.9

  of pyrazole containing pyrimidine, 1,4-dihydropyridine, and imidazole derivatives using substituted 4-formylpyrazole as a key intermediate via multicomponent reaction sequence. The structures of these unknown compounds were elucidated by IR, 1H NMR, 13C NMR, LC–MS, and elemental analysis. The synthesized products were screened for their in vitro antimicrobial and antioxidant properties. Among the tested

  摘要这项工作描述了新的一系列含有嘧啶，1,4-二氢吡啶和咪唑衍生物的吡唑的合成和表征，该衍生物通过多组分反应序列使用取代的4-甲酰基吡唑作为关键中间体。通过IR，1 H NMR，13 C NMR，LC-MS和元素分析阐明了这些未知化合物的结构。筛选合成产物的体外抗菌和抗氧化性能。在测试的3-（3,4-二卤代苯基）-1-苯基-1 H-吡唑-4-基中，掺入的乙酰基二氢嘧啶化合物显示出有希望的抗菌活性和DPPH自由基清除活性，其抑制水平分别为89.4％和83.3％ 。 图形概要
• Magnesium Sulphate-Catalyzed Green and Efficient Synthesis of Some New Derivatives of 1-Amido Alkyl Naphthols under Solvent-Free Conditions
  作者：Namdeo M. Chavhan、Sagar D. Bhakare、Rohit C. Muthe、Sayaji Y. Hande、Amol S. Gandule、Dhananjay N. Gaikwad、Dayanand M. Suryawanshi

  DOI：10.2174/1570178619666220113114613

  日期：2022.10

  The present work describes an efficient, green, and direct approach for the synthesis of amido alkyl naphthols via one-pot multicomponent solvent-free reaction (MCR) of substituted aromatic aldehydes, β-naphthols, and urea by the use of easily available, non-toxic, and cost-effective Lewis acid catalyst magnesium sulphate (MgSO4.7H2O). The important characteristics of this reaction include the following: eco-friendly and mild reaction conditions, excellent yields of the products, shorter reaction time, economically cheaper and environmentally friendly catalyst MgSO4.7H2O. Also, clean reaction, non-column purification, and operational simplicity are some of the additional significant features of this approach.

  摘要 本研究介绍了一种高效、绿色和直接的方法，通过一锅多组分无溶剂反应（MCR）合成氨基 烷基萘酚的高效、绿色、直接的合成方法。 醛、β-萘酚和尿素，并使用易于获得、无毒且经济高效的路易斯 酸催化剂硫酸镁（MgSO4.7H2O）。该反应的重要特点包括 环保、反应条件温和、产品收率高、反应时间短、经济实惠且环保。 反应时间，催化剂 MgSO4.7H2O 在经济上更便宜且更环保。此外，反应清洁 反应、非柱纯化和操作简便也是这种方法的一些重要特点。 此外，清洁反应、无柱纯化和操作简单也是这种方法的一些重要特点。