2,6-bis(4-fluorophenyl)-3,3-dimethylpiperidin-4-one | 1088437-54-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2,6-bis(4-fluorophenyl)-3,3-dimethylpiperidin-4-one
• CAS: 1088437-54-0
• 化学式: C₁₉H₁₉F₂NO
• 分子量: 315.363
• InChiKey: OUAMCQZZXCBUHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-bis(4-fluorophenyl)-3,3-dimethylpiperidin-4-one 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 3-(2,6-bis(4-fluorophenyl)-3,3-dimethylpiperidin-4-ylideneamino)-2-thioxoimidazolidin-4-one
  参考文献：
  名称：

  A facile microwave assisted green chemical synthesis of novel piperidino 2-thioxoimidazolidin-4-ones and theirin vitromicrobiological evaluation

  摘要：

  A series of novel hybrid heterocyclic compounds, 3-(3-alkyl-2,6-diarylpiperin-4-ylidene)-2-thioxoimidazolidin-4-ones were synthesised and a comparative study was also carried out under microwave irradiation. The synthesised compounds were characterised by their melting points, elemental analysis, MS, FT-IR, one-dimensional NMR (1H, D2O exchanged 1H and

  DOI：

  10.3109/14756361003691878
• 作为产物：
  描述：

  在 氨 作用下， 以 水 为溶剂， 生成 2,6-bis(4-fluorophenyl)-3,3-dimethylpiperidin-4-one
  参考文献：
  名称：

  Synthesis, spectral analysis and in vitro microbiological evaluation of 3-(3-alkyl-2,6-diarylpiperin-4-ylidene)-2-thioxoimidazolidin-4-ones as a new class of antibacterial and antifungal agents

  摘要：

  In the present work, a new series of bis hybrid heterocycle comprising both piperidine and thiohydantoin nuclei together namely 3-(3-alkyl-2,6-diarylpiperin-4-ylidene)-2-thioxoimidazolidin-4-ones 46-60 was synthesized by the treatment of the respective thiosemicarbazones 31-45 with chloroethyl acetate and anhydrous sodium acetate in refluxing ethanol for 4 h and were characterized by melting point, elemental analysis, MS, FT-IR, one-dimensional NMR (H-1, D2O exchanged H-1 and C-13), two dimensional HOMOCOSY and NOESY spectroscopic data. In addition, the title compounds were screened for their antimicrobial activities against a spectrum of clinically isolated microbial organisms. Compounds 47-50, 52-55 and 57-60 with fluoro, chloro, methoxy or methyl functions at the para position of phenyl rings attached to C-2 and C-6 carbons of piperidine moiety along with and without methyl substituent at position C-3 of the piperidine ring exerted potent biological activities againstStaphylococcus aureus, beta-Hemolytic streptococcus, Vibrio cholerae, Escherichia coli, Pseudomonas aeruginosa, Aspergillus flavus, Candida albicans, Candida 6 and Candida 51 at a minimum inhibitory concentration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.074

文献信息

• Synthesis, spectral, and computational studies of some energetic picrates
  作者：Kannan Gajendran Balachandar、Arumugam Thangamani

  DOI：10.1016/j.molstruc.2019.05.018

  日期：2019.11

  characterization of some of the thermodynamically stable energetic materials of c(3),t(3)-dimethyl-r(2),c(6)-diarylpiperidin-4-one picrates which are the analogues of the explosive D “The Dunnite”. c(3),t(3)-Dimethyl-r(2),c(6)-diarylpiperidin-4-one picrates have been synthesized by reacting c(3),t(3)-dimethyl-r(2),c(6)-diarylpiperidin-4-ones with picric acid in ethanol medium at room temperature. Spectral methods

  摘要 本工作讨论了 c(3),t(3)-二甲基-r(2),c(6)-diarylpiperidin-4-one picrates 的一些热力学稳定含能材料的合成和表征，它们是爆炸性的 D “Dunnite”。c(3),t(3)-Dimethyl-r(2),c(6)-diarylpiperidin-4-one picrates 已通过 c(3),t(3)-二甲基-r(2) 反应合成， c(6)-diarylpiperidin-4-ones 与苦味酸在乙醇介质中室温。光谱方法如 IR、1H NMR 和 13C NMR 用于表征合成的化合物。随后用标准方程研究了合成化合物的爆炸性能，并与LOTUSES代码模拟结果进行了比较。将这些含能材料的计算理化性质与苦味酸和邓尼特的理化性质进行了比较。
• Synthesis, stereochemical, structural and biological studies of some 2,6-diarylpiperidin-4-one N(4′)-cyclohexyl thiosemicarbazones
  作者：A. Sethukumar、C. Udhaya Kumar、R. Agilandeshwari、B. Arul Prakasam

  DOI：10.1016/j.molstruc.2013.05.008

  日期：2013.9

  Abstract A new series of 2,6-diarylpiperidin-4-one N(4′)-cyclohexyl thiosemicarbazones (13–23) were synthesized by corresponding 2,6-diarylpiperidin-4-ones (1–11) reaction with cyclohexyl thiosemicarbazide (12). The chemical structures were confirmed by means of IR, one and two dimensional NMR, Mass spectra and single crystal X-ray diffraction analysis. Compounds 13–23, exist in chair conformation

  摘要 通过相应的 2,6-二芳基哌啶-4-酮 (1-11) 与环己基氨基硫脲 (Semicarbazide) 反应合成了一系列新的 2,6-二芳基哌啶-4-one N(4')-环己基缩氨基硫脲 (13-23)。 12)。通过红外、一维和二维核磁共振、质谱和单晶X射线衍射分析证实了化学结构。化合物 13-23 以椅子构象存在，除化合物 21-23 的 C-5 处的甲基外，所有哌啶环上的取代基均呈赤道取向，以轴向排列以稳定椅子构象。化合物 18 的单晶 X 射线结构分析，证明 CN 双键的构型与 C-5 碳（E 型）同构。对所有合成的化合物进行了生物活性筛选。
• Synthesis, stereochemical and biological studies of some N-cyclohexylcarbamoyl -2,6-diarylpiperidin-4-ones
  作者：A. Sethukumar、P. Surendar Anand、C. Udhaya Kumar、B. Arul Prakasam

  DOI：10.1016/j.molstruc.2016.10.035

  日期：2017.2

  Abstract A series of N -cyclohexylcarbamoylpiperidin-4-ones were synthesized by the addition reaction of corresponding piperidin-4-ones with cyclohexylisocyanate in benzene. The structure and stereochemistry of the synthesized N- cyclohexylcarbamoyl -2, 6-diarylpiperidin-4-ones, were established on the basis of their analytical and spectral data (IR, 1 H and 13 C NMR). 2D NMR spectra (HOMOCOSY, HSQC

  摘要 通过相应的哌啶-4-酮与异氰酸环己酯在苯中的加成反应合成了一系列N-环己基氨基甲酰基哌啶-4-酮。合成的 N-环己基氨基甲酰基-2, 6-二芳基哌啶-4-酮的结构和立体化学是在它们的分析和光谱数据（IR、 1 H 和 13 C NMR）的基础上建立的。还记录了 2D NMR 光谱（HOMOCOSY、HSQC、HMBC 和 NOESY）以分析立体化学。在合成化合物的红外光谱中，观察到由于环和酰胺羰基官能团引起的特征吸收，这证明形成了 N-环己基氨基甲酰基-2, 6-二芳基哌啶-4-酮。NMR光谱结果与所合成化合物的建议结构一致。根据提取的耦合常数和 NOESY 光谱结果进行构象分析。评价合成的化合物的抗菌和抗真菌活性。
• Solvent-free one-pot synthesis, characterization, antibacterial and antifungal activities of novel spiropiperidinyl-1,2,4-triazolidine-3-thiones
  作者：V. Kanagarajan、J. Thanusu、M. R. Ezhilarasi、M. Gopalakrishnan

  DOI：10.1007/s10593-011-0720-5

  日期：2011.4

  A novel approach towards the synthesis of spiropiperidinyl 1,2,4-triazolidine-3-thiones was proposed, exploiting microwave activation coupled with solvent-free reaction conditions. In search for new leads towards potent antimicrobial agents, we tested all the synthesized compounds for their in vitro antibacterial activity against Bacillus subtilis and Micrococcus luteus and antifungal activity against Aspergillus niger, Candida albicans, Candida-6, and Candida-51. Two of the compounds exerted strong in vitro antibacterial activity against B. subtilis and M. luteus, and all the synthesized compounds were potent against the tested fungal strains.
• Synthesis and biological evaluation of 5,7-diaryl-4,4-dimethyl-4,5,6,7-tetrahydropyridino[3,4-d]-1,2,3-thiadiazoles
  作者：M. Gopalakrishnan、J. Thanusu、V. Kanagarajan

  DOI：10.1007/s00044-007-9051-6

  日期：2007.12

  New 5,7-diaryl-4,4-dimethyl-4,5,6,7-tetrahydropyridino[3,4-d]-1,2,3-thiadiazoles 23-27 are synthesized, characterized by melting point, elemental analysis, magnetic spectroscopy (MS), Fourier-transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR)(H-1 and C-13) spectra and evaluated for their in vitro antibacterial and antifungal activities. Compounds 23-27 are more potent against Gram-positive bacterial strains, namely Staphylococcus aureus and beta-Haemolytic streptococcus. However compounds 23-27 possess potent activity against Klebsiella pneumonia, a Gram-negative bacterial strain, compared to the standard drug used, ciprofloxacin. In general, all the synthesized compounds exert a wide range of modest in vitro antifungal activity against Rhizopus and Microsporum gypsuem than the standard drug, fluconazole.