3,5-dimethyl-2,6-bis(2-chlorophenyl)piperidine-4-one | 134645-34-4

• 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: 3,5-dimethyl-2,6-bis(2-chlorophenyl)piperidine-4-one
• 英文别名: 4-Piperidinone, 2,6-bis(2-chlorophenyl)-3,5-dimethyl-；2,6-bis(2-chlorophenyl)-3,5-dimethylpiperidin-4-one
• CAS: 134645-34-4
• 化学式: C₁₉H₁₉Cl₂NO
• 分子量: 348.272
• InChiKey: JSGCDAKRIPGQSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 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：

  3,5-dimethyl-2,6-bis(2-chlorophenyl)piperidine-4-one 在 N-溴代丁二酰亚胺(NBS) 、 mercury(II) diacetate 、 水 、 sodium acetate 、 溶剂黄146 作用下， 生成 2,6-Bis-(2-chloro-phenyl)-3-hydroxy-3,5-dimethyl-piperidin-4-one
  参考文献：
  名称：

  Meenal; Devi, D. Vimala, Journal of the Indian Chemical Society, 1996, vol. 73, # 7, p. 355 - 357

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-dimethyl-2,6-bis-(2-chlorophenyl)piperidin-4-one oxime 在 硫酸 、 水 、 溶剂黄146 、 quinolinium monofluorochromate(VI) 作用下， 生成 3,5-dimethyl-2,6-bis(2-chlorophenyl)piperidine-4-one
  参考文献：
  名称：

  Vimala; Jani Bai, Asian Journal of Chemistry, 2010, vol. 22, # 7, p. 5699 - 5704

  摘要：

  DOI：

文献信息

• 13C NMR chemical shifts, in someN-chloro-2,6-diarylpiperidin-4-ones
  作者：Misbah Ul Hasan、M. Arab

  DOI：10.1002/mrc.1260251113

  日期：1987.11

  The 13C shifts in several N-chloro-2,6-diarylpiperidin-4-ones have been measured and compared with previously reported sifts in the corresponding 2,6-diarylpiperidones. The shifts of the α-carbons in these compounds move downfield by 12–13 ppm, which can be attributed to the increased electronegativity of the nitrogen atoms. The changes in the chemical shifts of the β-carbons are minimal. Surprisingly, the absorptions of the carbonyl carbons move upfield by as much as 4.0 ppm. The magnitude of the shift in the resonance of the carbonyl carbon indicates the possibility of a transannular interaction between the nitrogen and the carbonyl group, which has not previously been observed in these systems. A preferred conformation for the aryl group in these compounds is also proposed.

  对几个N-氯-2,6-二芳基哌啶-4-酮的13C化学位移进行了测量，并与先前报告的相应2,6-二芳基哌啶酮的位移进行了比较。这些化合物中α碳的位移向下移动了12-13 ppm，这可以归因于氮原子电负性的增加。β碳的化学位移变化则很小。令人惊讶的是，羰基碳的吸收向上移动了多达4.0 ppm。羰基碳的共振位移幅度表明氮与羰基之间可能存在跨环相互作用，这在这些体系中尚未被观察到。此外，还提出了这些化合物中芳基的首选构象。
• Conformational analysis and13C NMR spectra of some 2,6-diarylpiperidin-4-ones
  作者：Misbah Ul Hasan、Mohammad Arab、K. Pandia Rajan、R. Sekar、Dale Marko

  DOI：10.1002/mrc.1260230503

  日期：1985.5

  on the basis of steric interactions taking place in the preferred conformations of these molecules. In compounds with o‐chloro groups, the aryl ring is oriented such that the chlorine is syn to the axial hydrogen on the aryl‐bearing carbon. The shielding effect of the carbonyl group is found to be more pronounced on an adjacent equatorial methyl than on an adjacent axial methyl group.

  已经测量了几种甲基取代的 2,6-二芳基-4-哌啶酮（芳基 = 苯基，邻氯苯基）的 13C NMR 光谱。甲基和氯的取代基参数也已经推导出来，并根据它们的空间和电子相互作用进行了讨论。C-3 上的甲基取代和苯环邻位上的氯取代都会导致 13C 化学位移发生显着变化，这可以基于这些分子的优选构象中发生的空间相互作用得到令人满意的解释。在带有邻氯基团的化合物中，芳环的取向使得氯与芳基碳上的轴向氢顺位。发现羰基的屏蔽作用对相邻的赤道甲基比对相邻的轴向甲基更显着。
• Synthesis, characterization, stereochemistry and biological investigation of certain N -dichloroacetyl- bis (2-chlorophenyl)piperidin-4-ones
  作者：R. Kayalvizhi、S. Ponnuswamy、K. Gomathi、K.S. Ezhilarasi、G. Usha

  DOI：10.1016/j.molstruc.2017.09.060

  日期：2018.2

  Abstract A new series of N -dichloroacetyl- bis (2-chlorophenyl)piperidin-4-ones 4-6 has been synthesized and characterized using IR, 1 H, 13 C, DEPT and 2D (COSY and HSQC) NMR spectral techniques. The NMR spectral data indicate that the N -acylpiperidin-4-ones 4-6 prefer to exist in an equilibrium between the twist boat conformations with coplanar orientation of N C O moiety. Furthermore, the antibacterial

  摘要 合成了一系列新的 N-二氯乙酰基-双 (2-氯苯基)哌啶-4-酮 4-6，并使用 IR、 1 H、 13 C、DEPT 和 2D (COSY 和 HSQC) NMR 光谱技术对其进行了表征。NMR 光谱数据表明，N-酰基哌啶-4-酮 4-6 更倾向于存在于扭曲船构象与 NCO 部分共面取向之间的平衡中。此外，已经对化合物 1-6 进行了抗菌和抗真菌研究，结果表明它们对细菌生物体金黄色葡萄球菌和副伤寒沙门氏菌具有显着的活性，并且对剩余的细菌生物体具有更好的活性。所有化合物1-6都具有中等的抗真菌活性。化合物4-6已经与MRSA的结构对接，结果证明化合物4-6在相互比较时具有相似的对接评分和滑动能量，因此具有相同的结合亲和力。抗氧化研究表明，与标准药物相比，化合物 4 的活性更高，而化合物 5 和 6 的活性较差。
• A facile synthesis, antibacterial, and antitubercular studies of some piperidin-4-one and tetrahydropyridine derivatives
  作者：Gopalakrishnan Aridoss、Shanmugasundaram Amirthaganesan、Nanjundan Ashok Kumar、Jong Tae Kim、Kwon Taek Lim、Senthamaraikannan Kabilan、Yeon Tae Jeong

  DOI：10.1016/j.bmcl.2008.10.045

  日期：2008.12

  The raise in clinical significance of multidrug-resistant bacterial pathogens has directed us to synthesize 2,6-diarylpiperidin-4-one and Delta(3)-tetrahydropyridin-4-ol based benzimidazole and O-arylsulfonyl derivatives. X-ray crystal structure of tetrahydropyridinol (23) confirmed a change in conformation and orientation of substituents upon amide formation. Antibacterial activities evaluated against a wide number of bacterial pathogens (both sensitive and multidrug-resistant) revealed that 19, 27 against Staphylococcus aureus, 27 against Enterococcus faecalis, and 19, 21, 23, and 27 against Enterococcus faecium are significantly good at lowest MIC90 (16 mu g/mL). Inhibitory power noticed by 23 against Vancomycin-Linezolid-resistant E. faecalis and 27 against Vancomycin-resistant E. faecium are onefold better than the standard Linezolid and Trovafloxacin drugs, respectively. Moreover, antitubercular activity for the selected compounds against Mycobacterium tuberculosis H37Rv revealed that compounds 23, 24, and 27 expressed onefold improved potency compared to the standard Rifampicin drug. (C) 2008 Elsevier Ltd. All rights reserved.
• Baskar; Gopalakrishnan; Jabaraj, J. Winfred, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 4, p. 580 - 584
  作者：Baskar、Gopalakrishnan、Jabaraj, J. Winfred

  DOI：——

  日期：——