4,4,4-trifluoro-1-(3-fluoro-4-methoxyphenyl) butane-1,3-dione | 70862-63-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4,4-trifluoro-1-(3-fluoro-4-methoxyphenyl) butane-1,3-dione
• 英文别名: 4,4,4-trifluoro-1-(3-fluoro-4-methoxyphenyl)butane-1,3-dione；3-fluoro-4-methoxybenzoyltrifluoroacetone；4,4,4-trifluoro-1-(3-fluoro-4-methoxy-phenyl)-butane-1,3-dione；1-(3-fluoro-4-methoxyphenyl)-4,4,4-trifluorobutane-1,3-dione
• CAS: 70862-63-4
• 化学式: C₁₁H₈F₄O₃
• mdl: MFCD11523446
• 分子量: 264.176
• InChiKey: RQGDMUVAUOVABM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,4,4-trifluoro-1-(3-fluoro-4-methoxyphenyl) butane-1,3-dione 在 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 30.0h， 生成 2,2,2-Trifluoro-1-[4-(3-fluoro-4-methoxy-phenyl)-8-phenyl-pyrazolo[5,1-c][1,2,4]triazin-3-yl]-ethanone
  参考文献：
  名称：

  Joshi; Pathak; Garg, Journal of the Indian Chemical Society, 1983, vol. 60, # 11, p. 1074 - 1076

  摘要：

  DOI：
• 作为产物：
  描述：

  三氟乙酸乙酯 、 3-氟-4-甲氧基苯乙酮 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 4,4,4-trifluoro-1-(3-fluoro-4-methoxyphenyl) butane-1,3-dione
  参考文献：
  名称：

  Synthesis, Fungicidal Activity and Mode of Action of 4-Phenyl-6-trifluoromethyl-2-aminopyrimidines against Botrytis cinerea

  摘要：

  苯胺嘧啶类是防治灰葡萄孢的主要化学药剂。然而，真菌对此类化合物的耐药性非常严重。为了探索新的防治灰葡萄孢的潜在杀菌剂，合成了一系列4-苯基-6-三氟甲基-2-氨基嘧啶类化合物(III-1至III-22)，并通过1H-NMR、IR和MS确认了其结构。这些化合物大多具有优异的杀菌活性。化合物III-3和III-13在果糖明胶琼脂(FGA)上的杀菌活性高于阳性对照嘧菌胺，化合物III-3在马铃薯葡萄糖琼脂(PDA)上的活性表明其与阳性对照环丙酰菌胺相比具有高活性。温室试验结果表明，化合物III-3、III-8和III-11的活性显著高于杀菌剂嘧菌胺。通过扫描电子显微镜(SEM)和透射电子显微镜(TEM)说明了这些化合物对灰葡萄孢的作用机制。这些化合物，特别是含有苯环上邻位氟原子的化合物，能够维持对灰葡萄孢的抗真菌活性，但其作用机制与环丙酰菌胺不同。本研究为我们寻找更高效的防治灰葡萄孢的药剂奠定了良好的基础。

  DOI：

  10.3390/molecules21070828

文献信息

• Catalytic and Asymmetric Process via P^III/P^V═O Redox Cycling: Access to (Trifluoromethyl)cyclobutenes via a Michael Addition/Wittig Olefination Reaction
  作者：Charlotte Lorton、Thomas Castanheiro、Arnaud Voituriez

  DOI：10.1021/jacs.9b02539

  日期：2019.7.3

  In the present study, we report the first enantioselective and highly efficient phosphine-catalyzed process via a chemoselective in situ phosphine oxide reduction. Starting with 4,4,4-trifluorobutane-1,3-dione and dialkyl acetylenedicarboxylate substrates, highly functionalized fluorinated cyclobutenes were obtained in excellent yields and enantioselectivities. Using the same methodology, CF3-spirocyclobutene

  在本研究中，我们报告了第一个通过化学选择性原位氧化膦还原对映选择性和高效膦催化的过程。从 4,4,4-三氟丁烷-1,3-二酮和乙炔二羧酸二烷基酯底物开始，以优异的产率和对映选择性获得了高度官能化的氟化环丁烯。使用相同的方法，还合成了 CF3-螺环丁烯衍生物（34 个实例，高达 95% ee）。
• Heterocyclic compounds process for their preparation and pharmceutical compositions containing them and their use in medicine
  申请人：Lohray B. Braj

  公开号：US20050277678A1

  公开（公告）日：2005-12-15

  The present invention describes novel compounds having antiinflamatory activity, process for their preparation and pharmaceutical composition containing them.

  本发明描述了具有抗炎活性的新化合物，其制备过程和含有它们的制药组合物。
• Investigation into the Synthesis, Bioactivity, and Mechanism of Action of the Novel 6-Pyrazolyl-2-picolinic Acid as a Herbicide
  作者：Qing Liu、Huiting Li、Rongchuan Shi、Wei Wei、Xiao Yuan、Yi-Ming Cao、Shangzhong Liu

  DOI：10.1021/acs.jafc.3c08517

  日期：2024.4.17

  retroflexus. Using compound V-2, the mechanism of action was investigated based on a phenotype study using AFB5-deficient Arabidopsis thaliana. It was found that the novel 6-pyrazolyl-2-picolinic acids were auxinic compounds. In addition, it was proposed that V-2 may be an immune activator due to its upregulation of defense genes and the increased content of jasmonic acid.

  设计并制备了一系列新型4-氨基-3,5-二氯-6-(5-芳基取代-1H-吡唑-1-基)-2-吡啶甲酸化合物来发现除草分子。测定了所有新化合物对拟南芥根生长的抑制活性。总体而言，新合成的化合物在500 μM浓度下表现出良好的抑制效果，并对杂草根部生长具有优异的除草活性。重要的是，一系列化合物表现出与毒莠定相当的除草特性。在250 g/ha的剂量下，大多数化合物对防治藜和反枝苋表现出100%的苗后除草活性。使用化合物V-2，基于使用AFB5缺陷的拟南芥的表型研究来研究其作用机制。结果发现，新型6-吡唑基-2-吡啶甲酸是植物生长素类化合物。此外，有人提出，V-2可能是一种免疫激活剂，因为它上调了防御基因并增加了茉莉酸含量。
• Discovery of a potent, selective and orally active canine COX-2 inhibitor, 2-(3-difluoromethyl-5-phenyl-pyrazol-1-yl)-5-methanesulfonyl-pyridine
  作者：Jin Li、Kristin M.Lundy DeMello、Henry Cheng、Subas M. Sakya、Brian S. Bronk、Robert J. Rafka、Burton H. Jaynes、Carl B. Ziegler、Carolyn Kilroy、Donald W. Mann、Eric L. Nimz、Michael P. Lynch、Michelle L. Haven、Nicole L. Kolosko、Martha L. Minich、Chao Li、Jason K. Dutra、Bryson Rast、Rhonda M. Crosson、Barry J. Morton、Glen W. Kirk、Kathleen M. Callaghan、David A. Koss、Andrei Shavnya、Lisa A. Lund、Scott B. Seibel、Carol F. Petras、Annette Silvia

  DOI：10.1016/j.bmcl.2003.10.004

  日期：2004.1

  Structure-activity relationship (SAR) studies of 2-[3-di(and tri)fluoromethyl-5-arylpyrazol-1-yl]-5-methanesulfonylpyridine derivatives for canine COX enzymes are described. This led to the identification of 12a as a lead candidate for further progression. The in vitro and in vivo activity of 12a for the canine COX-2 enzyme as well as its in vivo efficacy and pharmacokinetic properties in dog are highlighted. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis and SAR/3D-QSAR studies on the COX-2 inhibitory activity of 1,5-diarylpyrazoles to validate the modified pharmacophore
  作者：Sunil K. Singh、V. Saibaba、K. Srinivasa Rao、P. Ganapati Reddy、Pankaj R. Daga、S. Abdul Rajjak、Parimal Misra、Y. Koteswar Rao

  DOI：10.1016/j.ejmech.2005.03.016

  日期：2005.10

  Diverse analogs of 1,5-diarylpyrazoles having 3-hydroxymethyl-4-sulfamoyl (SO2NH2)/methyl sulfonyl (SO2Me)-pheny group at N-1 were synthesized and evaluated for their in vitro cyclooxygenase (COX-1/COX-2) inhibitory activity. The SAR study mainly involved the variations at positions C-3, C-5 and N-1 of the pyrazole ring. Several small hydrophobic groups at/around position-4 of C-5 phenyl, viz. 3,4-dimethylphenyl analog 9, 3-methyl-4-methylsulfanylphenyl analog 14 and 2,3-dihydrobenzo[b]thiophenyl analog 17, exhibited impressive COX-2 inhibitory potency. In general, the sulfonamide analogues with a CHF2 at C-3 were found to be more potent than those having a CF3 group. The three dimensional quantitative structure activity relationship comprising comparative molecular field analysis (3D-QSAR-CoMFA) afforded the models with high predictivity which further validated the acceptance of hydroxymethyl (CH2OH) group in the hydrophilic pocket of the COX-2 enzyme. (c) 2005 Elsevier SAS. All rights reserved.