1-(2,4-二甲基苯基)-4,4,4-三氟丁烷-1,3-二酮 | 94856-20-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2,4-二甲基苯基)-4,4,4-三氟丁烷-1,3-二酮
• 英文名称: 1-(2,4-Dimethylphenyl)-4,4,4-trifluorobutane-1,3-dione
• CAS: 94856-20-9
• 化学式: C₁₂H₁₁F₃O₂
• mdl: MFCD03420704
• 分子量: 244.213
• InChiKey: DSEGNKJPZXXYBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2,4-二甲基苯基)-4,4,4-三氟丁烷-1,3-二酮 在 乙酸酐 、 柠檬酸 、 sodium nitrite 作用下， 以 氯仿 、 水 为溶剂， 反应 2.0h， 生成 (2,4-dimethyl-phenyl)-glyoxylonitrile
  参考文献：
  名称：

  4,4,4-三氟-3,3-二羟基-2-（羟基亚氨基）丁-1-酮的三氟乙酰化作为酰基氰化物的简便合成策略

  摘要：

  氟化的1,3-二羰基化合物与NaNO 2在酸性条件下的反应重新研究表明，形成了相应的1,1,1-三氟-3-羟基亚氨基-丁酮-2,4-二酮，其主要以水合物形式分离。描述了通过酸催化的获得的1，3-二羰基化合物的2-羟基亚氨基衍生物的乙氧基-，烷基-，（杂）芳基取代的羰基氰化物的新颖合成。

  DOI：

  10.1016/j.jfluchem.2016.04.009
• 作为产物：
  描述：

  2,4-二甲基苯乙酮 以69%的产率得到1-(2,4-二甲基苯基)-4,4,4-三氟丁烷-1,3-二酮
  参考文献：
  名称：

  New Heterocyclic compounds for therapeutic use

  摘要：

  一类化合物，特别是通式1和2的二芳基吡唑化合物，其中R和R′代表烷基、氢、卤素、卤代烷基、氰基、硝基、甲酰基、羧基、烷氧羰基、羧基烷基、烷氧羰基烷基、羟基烷基、烷基硫基、烷基亚砜基、N-烷基磺酰胺基、N-芳基磺酰胺基、氰基酰胺基、氨基、氨基甲酰胺基、N-烷基氨基甲酰胺基、N-芳基氨基甲酰胺基、N,N-二烷基氨基甲酰胺基、N-烷基-N-芳基氨基甲酰胺基、N,N-二烷基磺酰胺基，其中每个这样的基团的烷基或烷基部分含有1-3个碳原子，或它们的混合物，必要时存在时，以及它们的制备方法。本发明的化合物具有抗炎、退热、抗风湿、抗骨关节炎活性和抗菌活性。具体的化合物类别如下（通式1和通式2）。

  公开号：

  US20010047023A1

文献信息

• Synthesis, Fungicidal Activity and Mode of Action of 4-Phenyl-6-trifluoromethyl-2-aminopyrimidines against Botrytis cinerea
  作者：Chunhui Liu、Zining Cui、Xiaojing Yan、Zhiqiu Qi、Mingshan Ji、Xinghai Li

  DOI：10.3390/molecules21070828

  日期：——

  Anilinopyrimidines are the main chemical agents for management of Botrytis cinerea. However, the drug resistance in fungi against this kind of compounds is very serious. To explore new potential fungicides against B. cinerea, a series of 4-phenyl-6-trifluoromethyl-2-amino-pyrimidine compounds (compounds III-1 to III-22) were synthesized, and their structures were confirmed by 1H-NMR, IR and MS. Most of these compounds possessed excellent fungicidal activity. The compounds III-3 and III-13 showed higher fungicidal activity than the positive control pyrimethanil on fructose gelatin agar (FGA), and compound III-3 on potato dextrose agar (PDA) indicated high activity compared to the positive control cyprodinil. In vivo greenhouse results indicated that the activity of compounds III-3, III-8, and III-11 was significantly higher than that of the fungicide pyrimethanil. Scanning electron micrography (SEM) and transmission electron micrography (TEM) were applied to illustrate the mechanism of title compounds against B. cinerea. The title compounds, especially those containing a fluorine atom at the ortho-position on the benzene ring, could maintain the antifungal activity against B. cinerea, but their mechanism of action is different from that of cyprodinil. The present study lays a good foundation for us to find more efficient reagents against B. cinerea.

  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。
• 一种1,5-二芳基吡唑衍生物、合成方法及用途
  申请人：江苏食品药品职业技术学院

  公开号：CN113045498B

  公开（公告）日：2023-01-24

  本发明涉及一种1,5‑二芳基吡唑衍生物及其抗菌应用，本发明在塞来昔布结构基础上对1,5‑二芳基进行结构修饰得到1,5‑二芳基吡唑衍生物，合成得到的目标分子经结构确证后进行抗菌活性体内外研究。本发明的1,5‑二芳基吡唑衍生物具有较好的抗菌活性，可用于细菌的抗感染治疗，为临床上细菌感染提供更多的用药选择。
• Synthesis and Biological Evaluation of the 1,5-Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors:  Identification of 4-[5-(4-Methylphenyl)-3- (trifluoromethyl)-1<i>H</i>-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib)
  作者：Thomas D. Penning、John J. Talley、Stephen R. Bertenshaw、Jeffery S. Carter、Paul W. Collins、Stephen Docter、Matthew J. Graneto、Len F. Lee、James W. Malecha、Julie M. Miyashiro、Roland S. Rogers、D. J. Rogier、Stella S. Yu、Gary D. Anderson、Earl G. Burton、J. Nita Cogburn、Susan A. Gregory、Carol M. Koboldt、William E. Perkins、Karen Seibert、Amy W. Veenhuizen、Yan Y. Zhang、Peter C. Isakson

  DOI：10.1021/jm960803q

  日期：1997.4.1

  A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC-236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of ii (4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.
• 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.
• HETEROCYCLIC COMPOUNDS FOR THERAPEUTIC USE
  申请人：J.B. Chemicals & Pharmaceuticals Ltd.

  公开号：EP1377289A2

  公开（公告）日：2004-01-07