3-Methyl-2,6-bis-(4-brom-phenyl)-piperidin-4-on | 17040-76-5

• 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: 3-Methyl-2,6-bis-(4-brom-phenyl)-piperidin-4-on
• 英文别名: 2,6-bis-(4-bromo-phenyl)-3-methyl-piperidin-4-one；2,6-Bis(4-bromophenyl)-3-methylpiperidin-4-one
• CAS: 17040-76-5
• 化学式: C₁₈H₁₇Br₂NO
• 分子量: 423.147
• InChiKey: CHAPIWAQAKVDIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  3-Methyl-2,6-bis-(4-brom-phenyl)-piperidin-4-on 在 盐酸羟胺 、 sodium acetate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 (E)-2,6-bis(4-bromophenyl)-3-methyl-1-(prop-2-yn-1-yl)piperidin-4-one oxime
  参考文献：
  名称：

  Synthesis, characterization, computational calculation and biological studies of some 2,6-diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oxime derivatives

  摘要：

  A new series of 2,6-diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oximes (17-24) were designed and synthesized from 2,6-diarylpiperidin-4-one oximes (9-16) with propargyl bromide. Unambiguous structural elucidation has been carried out by investigating IR, NMR (H-1, C-13, H-1-H-1 COSY and HSQC), mass spectral techniques and theoretical (DFT) calculations. Further, crystal structure of compound 17 was evaluated by single crystal X-ray diffraction analysis. Single crystal X-ray structural analysis of compound 17 evidenced that the configuration about C=N double bond is syn to C-5 carbon (E-form). The existence of chair conformation was further confirmed by theoretical DFT calculation. All the synthesized compounds were screened for in vitro antimicrobial activity against a panel of selected bacterial and fungal strains using Ciprofloxacin and Ketoconazole as standards. The minimum inhibition concentration (MIC) results revealed that most of the 2,6-diaryl-1-(prop-2-yn-1-yl)piperidin-4-one oximes (17, 19, 20 and 23) exhibited better activity against the selected bacterial and fungal strains. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2014.12.014
• 作为产物：
  描述：

  对溴苯甲醛 、 丁酮 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以88%的产率得到3-Methyl-2,6-bis-(4-brom-phenyl)-piperidin-4-on
  参考文献：
  名称：

  交联的聚苯乙烯/四氯化钛为紧密结合的络合物，催化了修饰的曼尼希反应，用于合成哌啶-4-酮

  摘要：

  制备交联的聚苯乙烯珠粒，对其进行表征，并通过聚苯乙烯与TiCl 4的络合作用将所得的聚合物载体用四氯化钛（TiCl 4）官能化，得到相应的交联的聚苯乙烯-TiCl 4稳定的络合物（PSt / TiCl 4一步反应，并通过FT-IR，UV，TGA，DSC，XRD，SEM，BET对其进行表征。这种紧密结合的配位化合物被用作耐水，多相，可回收和可重复使用的路易斯酸催化剂，用于通过酮，芳族醛和乙酸铵在1：中的修饰的曼尼希多组分缩合反应合成取代的哌啶-4-酮。在温和条件下的比例为2：1M。发现反应速率随着交联百分比和共聚物珠粒的筛孔尺寸的增加而降低。该催化剂是耐水的，稳定的，并且可以容易地回收和重复使用至少四次而没有任何活性损失。

  DOI：

  10.1016/j.jorganchem.2019.04.004

文献信息

• Synthesis, characterization, crystal structure, in-vitro antimicrobial evaluation and molecular docking studies of 1-(furan-2-carbonyl)-3-alkyl-2,6-diphenylpiperidin-4-one derivatives
  作者：R. Srikanth、A. Sivarajan、C.S. Venkatesan、V. Maheshwaran、P. Sugumar、G. Rajitha、J.C. Varalakshmi、M.N. Ponnuswamy

  DOI：10.1016/j.molstruc.2016.07.023

  日期：2016.12

  Abstract A new class of various furoyl derivatives of 2,6-disubstituted piperidin-4-ones were synthesized and characterized by FTIR, NMR, mass and single crystal X-ray diffraction methods. The synthesized compounds were subjected to in-vitro antibacterial and antifungal activities against pathogenic microbial strains. The results pointed out that compounds 11, 12 & 14 displayed pronounced activity

  摘要 合成了一类新的2,6-二取代哌啶-4-酮的呋喃酰基衍生物，并采用FTIR、NMR、质谱和单晶X射线衍射方法对其进行了表征。合成的化合物对病原微生物菌株进行体外抗菌和抗真菌活性。结果表明化合物11、12和14对革兰氏阳性菌显示出明显的活性，而化合物9、13和14对革兰氏阴性菌显示出优异的抑制活性。化合物9对真菌表现出中等活性。此外，还进行了分子对接实验。
• 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, spectral and biological evaluation of some new thiazolidinones and thiazoles based on t-3-alkyl-r-2,c-6-diarylpiperidin-4-ones
  作者：G. Aridoss、S. Amirthaganesan、M.S. Kim、J.T. Kim、Yeon Tae Jeong

  DOI：10.1016/j.ejmech.2009.05.015

  日期：2009.10

  A stereospecific synthesis of some thiazolidinones and thiazoles was achieved conveniently through certain α-halo keto agents and reactivity of chloroacetyl chloride was successfully enhanced by CsF–Celite + CH3COONa. NMR studies revealed that the configuration of N–N bond is found to be anti with respect to C-3 alkyl group while CN bond in thiazolidinone is trans with respect to N–N bond. Antimycobacterial

  通过某些α-卤代酮试剂可方便地实现一些噻唑烷酮和噻唑的立体定向合成，并且CsF–Celite + CH 3 COONa成功提高了氯乙酰氯的反应性。NMR研究表明，N-N键的构型被发现是抗相对于C-3的烷基而C N键在噻唑烷酮是反相对于N-N键。对所测试的抗分支杆菌活性的结核分枝杆菌表明化合物19，20，24，29，30和32表现出比利福平高两倍的效力。类似地，抗微生物筛选研究指出，化合物21和28个特别注意到有前途的活性，特别是，21针对金黄色葡萄球菌和，24和32对根霉属。与环丙沙星和两性霉素B相比，抗肺炎克雷伯菌的抑制力提高了一倍，而21抑制力提高了两倍。