2,6-di(p-tolyl)3-methylpiperidin-4-one | 201335-52-6

• 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-di(p-tolyl)3-methylpiperidin-4-one
• 英文别名: 3-methyl-2,6-di(p-tolyl)piperidine-4-one；3-Methyl-2,6-bis(4-methylphenyl)piperidin-4-one
• CAS: 201335-52-6
• 化学式: C₂₀H₂₃NO
• 分子量: 293.409
• InChiKey: CIIGQBBCLUPVRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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-di(p-tolyl)3-methylpiperidin-4-one 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 3-(3-methyl-2,6-di-p-tolylpiperidin-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-di(p-tolyl)3-methylpiperidin-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

• Stereoselective synthesis and spectral studies of some benzotriazolylacetyl hydrazones of 3–alkyl–2,6–diarylpiperidin–4–ones
  作者：M. Velayutham Pillai、K. Rajeswari、C. Udhaya Kumar、K. Gokula Krishnan、S. Mahendran、C. Ramalingan、E.R. Nagarajan、T. Vidhyasagar

  DOI：10.1016/j.molstruc.2017.09.010

  日期：2017.12

  benzotriazole nucleus into piperidine ring is achieved through hydrazone formation. The characterization of the synthesized compounds was carried out using FT-IR, 1H &13C NMR, 1H–1H COSY, 1H–13C COSY, NOESY spectral techniques and GC-Mass spectrum. The spectral assignments were done without ambiguity using 2D-NMR techniques. The conformational preference of the piperidine ring deduced from the spectral

  摘要 通过腙的形成，努力将具有生物活性的苯并三唑核包含在哌啶环中。合成化合物的表征使用 FT-IR、1H 和 13C NMR、1H-1H COSY、1H-13C COSY、NOESY 光谱技术和 GC-质谱进行。使用 2D-NMR 技术毫无歧义地完成了光谱分配。从光谱研究中推导出的哌啶环的构象偏好是“椅子”。分子中存在的亚甲基质子/甲基的非对映性质在观察到的光谱模式中清楚地显示出来。
• Stereoselective synthesis, spectral and antimicrobial studies of some cyanoacetyl hydrazones of 3-alkyl-2,6-diarylpiperidin-4-ones
  作者：M. Velayutham Pillai、K. Rajeswari、T. Vidhyasagar

  DOI：10.1016/j.molstruc.2014.07.050

  日期：2014.11

  Abstract A series of novel cyanoacetyl hydrazones of 3-alkyl-2,6-diarylpiperidin-4-ones were synthesized stereoselectively and characterized by IR, Mass, 1 H NMR, 13 C NMR, 1 H– 1 H COSY and 1 H– 13 C COSY spectra. The stereochemistry of the synthesized compounds was established using NMR spectra. Antimicrobial screening of the synthesized compounds revealed their antibacterial and antifungal potencies

  摘要 立体选择性地合成了一系列 3-烷基-2,6-二芳基哌啶-4-酮的新型氰基乙酰腙，并通过红外、质谱、 1 H NMR、 13 C NMR、 1 H– 1 H COZY 和 1 H– 13 表征。 C 舒适光谱。合成化合物的立体化学是通过核磁共振谱确定的。合成化合物的抗菌筛选揭示了它们的抗菌和抗真菌效力。发现化合物 15 对产气肠杆菌的生长抑制优于标准药物。
• Chemoselective synthesis and spectral studies of <i>N</i>-thiocyanatoacetyl derivatives of 3-alkyl-2,6-diarylpiperidin-4-ones
  作者：M. Velayutham Pillai、K. Rajeswari、C. Udhaya Kumar、C. Ramalingan、A. Manohar、T. Vidhyasagar

  DOI：10.1080/10426507.2016.1149852

  日期：2016.9.1

  of the respective piperidin–4–ones and the ambident thiocyanate nucleophile. The synthesized compounds have been characterized through FT–IR, 1H, 13C, 1H–1H COSY, 1H–13C COSY and NOESY spectra. The spectral data reveal the conformational priority of the six-membered heterocyclic ring.

  图形摘要 摘要 3-烷基-2,6-二芳基哌啶-4-酮的一系列N-硫氰酸根合乙酰基衍生物已通过各自哌啶-4-酮的N-氯乙酰衍生物与中间硫氰酸酯亲核试剂之间的反应合成。合成的化合物已通过 FT-IR、1H、13C、1H-1H COSY、1H-13C COSY 和 NOESY 光谱进行表征。光谱数据揭示了六元杂环的构象优先级。
• 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。
• Synthesis and NMR spectral studies of some 2,6-diarylpiperidin-4-one O-benzyloximes
  作者：P. Parthiban、S. Balasubramanian、G. Aridoss、S. Kabilan

  DOI：10.1016/j.saa.2007.07.059

  日期：2008.6

  Variously substituted 2,6-diarylpiperidin-4-one O-benzyloximes were synthesized by the direct condensation of the corresponding 2,6-diarylpiperidin-4-ones with O-benzylhydroxylamine hydrochloride. All the synthesized compounds are characterized by IR, Mass and NMR spectral studies. NMR spectral assignments are made unambiguously by their one-dimensional (1H NMR and 13C NMR) and two-dimensional (1H-1H

  通过将相应的2，6-二芳基哌啶-4-酮与O-苄基羟胺盐酸盐直接缩合，合成了各种取代的2，6-二芳基哌啶-4-酮O-苄基肟。所有合成的化合物均通过IR，质谱和NMR光谱进行表征。NMR光谱分配通过其一维（1H NMR和13C NMR）和二维（1H-1H COSY，NOESY，HSQC和HMBC）NMR谱明确地指定。所有合成的化合物均为单一异构体，即仅是E异构体（9-14）。还使用光谱研究讨论了在C-3和C-5处带有和不带有烷基取代基的2,6-二芳基哌啶-4-酮肟醚的构象偏爱。观察到的化学位移和偶联常数表明，化合物8-13采用具有所有取代基的赤道取向的正常椅构象，而化合物14与溶液中的主要椅构象一起贡献了显着的舟形。研究了氧化对环碳，其相关质子，烷基取代基和ipso碳的影响。观察到肟醚的哌啶酮环中的每个质子由于氧化而作为不同的信号。化合物8中化学位移的大小顺序为H-2a> H-6a> H-5e>