2,6-bis(4-chlorophenyl)-3,3-dimethylpiperidin-4-one | 1088437-52-8

• 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-chlorophenyl)-3,3-dimethylpiperidin-4-one
• 英文别名: BCDP；2,6-Bis(4-chlorophenyl)-3,3-dimethylpiperidin-4-one
• CAS: 1088437-52-8
• 化学式: C₁₉H₁₉Cl₂NO
• 分子量: 348.272
• InChiKey: NNZQNGKTUYDPHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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：
  2

反应信息

• 作为反应物：
  描述：

  2,6-bis(4-chlorophenyl)-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-chlorophenyl)-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-chlorophenyl)-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 characterization, solution and solid-state conformations of N-nitroso-2,7-diaryl-1,4-diazepan-5-ones by NMR and XRD studies
  作者：S. Sethuvasan、P. Sugumar、M.N. Ponnuswamy、S. Ponnuswamy

  DOI：10.1016/j.molstruc.2020.129002

  日期：2021.1

  on the basis of chemical shifts, coupling constants and dihedral angles. In solution state, syn and anti rotamers of the compounds 9–11 exist in equilibrium between flattened boat conformation with quasi-axial orientations of the aryl groups at C-2 and C-7. Nevertheless, compound 12 and its syn and anti rotamers prefer to adopt equilibrium between chair conformations with axial orientation of aryl substituents

  摘要 合成了 2,7-diaryl-1,4-diazepan-5-ones 9-12 的亚硝基衍生物，并使用光谱技术如 IR、EI-MS 和 NMR 光谱对其进行了表征。亚硝基化合物的立体化学研究已使用 1D (1H, 13C & DEPT-135) 和 2D (COSY & HSQC) NMR 光谱数据进行。9-12 的旋转异构体（同和反旋转异构体）通过室温 NMR 光谱研究进行鉴定和分类。此外，环的构象和 NN=O 函数的取向是根据化学位移、耦合常数和二面角得出的。在溶液状态下，化合物 9-11 的顺式和反式旋转异构体在扁平的船形构象与 C-2 和 C-7 处芳基的准轴取向之间处于平衡状态。尽管如此，化合物 12 及其顺式和反旋转异构体倾向于在具有芳基取代基轴向取向的椅式构象之间采用平衡。为了验证溶液状态的构象，化合物12被结晶并且通过单晶XRD研究来解析晶体结构。化合物 12 以交替的椅子构象存在，并且
• Synthesis, spectral characterization, crystal structure and molecular docking study of 2,7-diaryl-1,4-diazepan-5-ones
  作者：S. Sethuvasan、P. Sugumar、V. Maheshwaran、M.N. Ponnuswamy、S. Ponnuswamy

  DOI：10.1016/j.molstruc.2016.03.021

  日期：2016.7

  prefer a chair conformation with equatorial orientation of alkyl and aryl groups. Single crystal X-ray structure has been solved for compounds 9 and 11 which also indicates the preference for distorted chair conformation with equatorial orientation of substituents. The compounds 9 – 16 have been docked with the structure of Methicillin-resistant Staphylococcus aureus (MRSA) and the results demonstrate that

  摘要 在本研究中，使用施密特重排合成了一系列不同取代的 r -2, c -7-diaryl-1,4-diazepan-5-ones 9 – 16，并通过红外、质谱和 1D 和 2D NMR 表征。光谱数据。质子 NMR 耦合常数和估计的二面角表明化合物 9-16 更喜欢具有烷基和芳基赤道取向的椅子构象。已解析化合物 9 和 11 的单晶 X 射线结构，这也表明偏爱具有赤道取向取代基的扭曲椅子构象。化合物9-16与耐甲氧西林金黄色葡萄球菌(MRSA)的结构对接，结果表明化合物10的对接分数和滑动能量优于其他化合物，与共晶配体相当。此外，所有化合物均已评估其抗菌和抗氧化活性。所有化合物均表现出中等抗菌活性，只有11种化合物对金黄色葡萄球菌和大肠杆菌表现出更好的活性。与BHT相比，化合物11、13和14表现出一半的抗氧化能力，而其余化合物表现出中等活性。
• 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。
• Photophysical Properties of Novel Picrate Derivatives – Solvent Effect
  作者：Jayaraman Jayabharathi、Venugopal Thanikachalam、Manoharan Padmavathy、Marimuthu Venkatesh Perumal

  DOI：10.1007/s10895-011-0957-5

  日期：2012.1

  H and 13C NMR spectra were recorded for some novel picrate derivatives derived from 3,3-dimethyl-2,6-diarylpiperidin-4-ones and 3-benzyl-2,6-diarylpiperidin-4-one. The photophysical properties of the picrate derivatives were studied in several solvents, which include a wide range of apolar, polar and protic media. The observed lower fluorescence quantum yield may be due to an increase in the non-radiative deactivation rate constant. This is attributed due to the presence of increased electrostatic interaction between N-protonated piperidone ring and picryl anion ring so that the picryl anion ring lies perpendicular to the plane of the N-protonated piperidone ring i.e., non co-planarity. Such a geometrical change in the excited state leads to an important Stokes shift, reducing the reabsorption and reemission effects in the detected emission in highly concentrated solutions. The higher fluorescence quantum yield of the picrate derivatives are observed in polar media.

  研究人员记录了一些由 3,3-二甲基-2,6-二芳基哌啶-4-酮和 3-苄基-2,6-二芳基哌啶-4-酮衍生的新型苦味酸盐衍生物的 H 和 13C NMR 光谱。研究人员在几种溶剂（包括各种非极性、极性和原生介质）中对皮酸盐衍生物的光物理特性进行了研究。观察到的较低荧光量子产率可能是由于非辐射失活速率常数的增加。这是因为 N-质子化哌啶酮环和吡啶基阴离子环之间的静电作用增强，从而使吡啶基阴离子环垂直于 N-质子化哌啶酮环的平面，即非共平面性。激发态的这种几何变化会导致重要的斯托克斯偏移，从而降低高浓度溶液中检测到的发射中的重吸收和再发射效应。在极性介质中可以观察到皮酸盐衍生物的荧光量子产率更高。
• Synthesis, crystal structure, Hirshfeld surface analysis, DFT, molecular docking and molecular dynamic simulation studies of (E)-2,6-bis(4-chlorophenyl)-3-methyl-4-(2-(2,4,6-trichlorophenyl)hydrazono)piperidine derivatives
  作者：L. Athishu Anthony、D. Rajaraman、G. Sundararajan、M. Suresh、P. Nethaji、R. Jaganathan、Kumaradhas Poomani

  DOI：10.1016/j.molstruc.2022.133483

  日期：2022.10

  hydrogen bonds. From the geometrical parameters, it is observed that the piperidine ring adopts chair conformation. Hirshfeld surface analysis was carried out to quantify the interactions and an interaction energy analysis was done to study the interactions between pairs of molecules. The geometrical structure was optimized by density functional theory (DFT) method at B3LYP/6-31G (d, p) as the basic set.

  一种治疗 SARS-CoV-2 感染的新药和羟氯喹类似物，( E)-2,6-双(4-氯苯基)-3-甲基-4-(2-(2,4,6-三氯苯基)亚肼基)哌啶(BCMTP)化合物已通过一锅反应合成。新型化合物BCMTP已通过 FT-IR、1 H-NMR、13 C-NMR 和单晶 X 射线衍射图谱进行了表征。C8-H8A•••Cl10 i , C41-H41•••Cl1 ii和N1-H1A•••Cl6 iii稳定晶体堆积分子间氢键。从几何参数来看，哌啶环呈椅形构象。进行了 Hirshfeld 表面分析以量化相互作用，并进行了相互作用能分析以研究分子对之间的相互作用。以B3LYP/6-31G (d, p)为基本集，通过密度泛函理论（DFT）方法对几何结构进行了优化。结合能值越小，BCMTP的反应活性越高化合物比羟基氯喹高，并通过高亲电和低亲核反应得到纠正。自然键轨道 (NBO) 分析还考虑了分子的稳定性和电荷离域。HOMO-LUMO