cis-2,6-diphenyl-trans-3-methylpiperidin-4-one

• 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: cis-2,6-diphenyl-trans-3-methylpiperidin-4-one
• 英文别名: r-2,c-6-diphenyl-t-3-methylpiperidin-4-one；(2S,3R,6R)-3-methyl-2,6-diphenylpiperidin-4-one
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: IKSGNXSKFBMJLS-XCRHUMRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 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：

  cis-2,6-diphenyl-trans-3-methylpiperidin-4-one 在 盐酸 、 sodium azide 、 硫酸 作用下， 以85%的产率得到3-methyl-cis-2,7-diphenyl-1,2,3,4,6,7-hexahydro-1,4-diazepin-5-one
  参考文献：
  名称：

  Chemistry of N-Nitroso Compounds. 7. Conformational Preferences of Hexahydro-N1,N4- dinitroso-r-2,c-7-diphenyl-1H-1,4-diazepines: Use of Modified 1D HOHAHA and NOE Techniques

  摘要：

  Modified HOHAHA and NOE experiments on three N,N'-dinitrosohexahydrodiazepines, at temperatures ranging from -50 degrees C to +120 degrees C, indicated that each of the title compounds exists as an equilibrium mixture of two families of conformations, the major family consisting of four rotamers and the minor consisting of, possibly, four rotamers resulting from two parallel dynamic processes viz., the restricted N-N rotation at two N-NO bonds and the pseudorotation of the seven-membered ring. The 3-isopropyl derivative 10, at +50 degrees C, exhibited only four resonances for each kind of proton/carbon, indicating that the rate of pseudorotation is fast compared to the NMR time scale. The H-1 resonances, broad at room temperature, became decoalesced at -50 degrees C as a result of the slow pseudorotation process. In all the three dinitroso compounds, of the two sets of twist-chair conformers, the major rotamers (similar to 95%) have the alkyl group (at C3) axially disposed while the minor rotamers have quasiequatorial alkyl groups. On the other hand, the alkyl group at C6 of the 3,6-dimethyl derivative 11 adopts equatorial orientation in all its conformers.

  DOI：

  10.1021/jo00128a018
• 作为产物：
  描述：

  t(3)-甲基-r(2),c(6)-二苯基哌啶-4-酮 在 sodium hydrogen sulfate 、 硫酸 、 thallium(III) acetate 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 24.0h， 生成 cis-2,6-diphenyl-trans-3-methylpiperidin-4-one
  参考文献：
  名称：

  Daniel Yesudian; Christopher Newton Benny; Ananthakrishna Nadar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 8, p. 675 - 678

  摘要：

  DOI：

文献信息

• Conformational analysis of 2,6-diarylpiperidin-4-one hydrazones by X-ray diffraction and NMR spectroscopy
  作者：C. Sankar、S. Umamatheswari、K. Pandiarajan

  DOI：10.1016/j.molstruc.2014.10.015

  日期：2015.3

  derived from the condensation of 3t-alkyl-2r,6c-diarylpiperidin-4-ones with isoniazid (INH) is reported. Newly synthesized compounds have been characterized by using elemental analysis, IR, 1H, 13C and 2D NMR spectral analysis. Moreover, representative crystal structure of 3,3-dimethyl-2r,6c-diarylpiperidin-4-one N-isonicotinoylhydrazone has been determined by X-ray diffraction analysis. NMR data revealed

  摘要 由 3t-烷基-2r,6c-diarylpiperidin-4-ones 与异烟肼 (INH) 缩合得到的一系列新的 3t-烷基-2r,6c-diarylpiperidin-4-one N-异烟酰腙 (12-22) 是报道。新合成的化合物已通过元素分析、IR、1H、13C 和 2D NMR 光谱分析进行了表征。此外，3,3-二甲基-2r,6c-diarylpiperidin-4-one N-异烟酰腙的代表性晶体结构已通过 X 射线衍射分析确定。核磁共振数据显示，在所有情况下都形成了两种几何异构体（E 和 Z），并且哌啶环采用椅子构象。而在固态下，化合物在 CN 键周围具有 E 构型。这些结论也得到了化合物 16 的 X 射线数据的证实。
• Facile synthesis of N-benzylated 3-alkyl-2,6-diarylpiperidin-4-ones: Stereochemical investigation by 1D/2D NMR and single-crystal XRD
  作者：Someshwar D. Dindulkar、Paramasivam Parthiban、Vedavati G. Puranik、Yeon Tae Jeong

  DOI：10.1016/j.molstruc.2010.12.054

  日期：2011.3

  1H and 13C NMR spectral studies. Of them, the 1-benzyl-3-ethyl-2,6-diphenylpiperidin-4-one 22 was completely characterized by 2D NMR techniques such as 1H 1H COSY, 1H 13C COSY and NOESY to assign the signals, unambiguously. The proton coupling constants and NOE correlations provided the complete stereochemistry of 22, which is further witnessed by its single-crystal XRD analysis. The NMR and XRD studies

  摘要 以 87-92% 的高产率方便地合成了一系列 13 个 1-benzyl-3-alkyl-2,6-diarylpiperidin-4-ones 14-26。为了找到对哌啶酮立体化学的影响，除了 N-苄基化之外，还引入了 C-3 上的甲基/乙基/异丙基和 C-2/C-6 上苯环上的卤素/烷基/烷氧基/苄氧基。所有合成的化合物均通过质量、1H 和 13C NMR 光谱研究进行表征。其中，1-benzyl-3-ethyl-2,6-diphenylpiperidin-4-one 22 通过 1H 1H COSY、1H 13C COSY 和 NOESY 等 2D NMR 技术完全表征，明确分配信号。质子耦合常数和 NOE 相关性提供了 22 的完整立体化学，其单晶 XRD 分析进一步证明了这一点。NMR 和 XRD 研究表明，化合物 22 以椅子构象存在，所有取代基在溶液和固态下均呈赤道取向。根据它们的邻位偶联常数，所有化合物
• Synthesis of polyfunctionalized piperidone oxime ethers and their cytotoxicity on HeLa cells
  作者：Paramasivam Parthiban、Ramjee Pallela、Se-Kwon Kim、Dong Ho Park、Yeon Tae Jeong

  DOI：10.1016/j.bmcl.2011.09.063

  日期：2011.11

  the phenyl at C-2 and C-6 in association with/without methyl substituent on the secondary amino group and methyl/ethyl/isopropyl substituents on the active methylene centers. Regardless of their substitution all compounds predominantly exist in the chair conformation except 3m, which adopts a twist-boat conformation. All the synthesized compounds were evaluated for their in vitro antiproliferative activity

  合成了一系列二十个2,6-二芳基哌啶-4-一O-甲基肟，在C-2和C-6的苯基的各个位置上都有氟/氯/溴/甲基/甲氧基/乙氧基/异丙基取代基，与/在仲氨基上没有甲基取代基，在活性亚甲基中心上没有甲基/乙基/异丙基取代基。不论它们的取代方式是什么，所有化合物都主要存在于椅子构象中，除了3m，它采用的是扭曲船构型。评价所有合成的化合物对人宫颈癌（HeLa）细胞系的体外抗增殖活性。通过用MTT测定法测量处理24小时后的活细胞数来确定测试化合物的细胞毒性。初步的SAR结果表明，一些铅分子3c-f，3j-k，4d-g和4i具有对哌啶酮药效团进一步结构优化的范围，以促进抗癌药物合成的发展。
• Stereochemical effect on biological activities of new series of piperidin-4-one derivatives
  作者：Periyasamy Venkatesan、Thiyagarajan Maruthavanan

  DOI：10.1080/14786419.2015.1009456

  日期：2015.11.17

  synthesised by the reduction of cis-3-alkyl-2,6-diarylpiperidin-4-one using Grignard reagent. The structural assignments and conformational studies of the synthesised compounds were established based on the IR, 1H NMR, 13C NMR, NOESY and mass spectral studies. Their stereochemical effect on antibacterial, antifungal and anthelmintic activities was studied.

  通过还原顺-3-烷基-2,6-合成了一系列新的（2 S，3 R，4 S，6 R）-3-甲基-4-烷基-2,6-二芳基哌啶-4-醇。使用格氏试剂制备二芳基哌啶-4-酮。基于IR，1 H NMR，13 C NMR，NOESY和质谱研究建立了合成化合物的结构分配和构象研究。研究了它们的立体化学作用对抗菌，抗真菌和驱虫活性的影响。
• New thiazoldinone substituted 2,6-diarypiperidin-4-one: Synthesis, crystal structure, spectral characterization, binding mode with calf thymus DNA
  作者：P. Sangeetha、C. Sankar、K. Tharini

  DOI：10.1016/j.molstruc.2019.126899

  日期：2019.12

  IR-120H resin under microwave irradiation. All the compounds were characterized by elemental analysis, FT-IR, 1H, 13C NMR spectra. The conformation of the compound was unambiguously assigned by 2D NMR spectral analysis. Single crystal X-ray diffraction recorded for compound 21 and the data indicate that the compound crystallized in triclinic system with space group Pī. The observed chemical shifts and coupling

  摘要 在微波照射下，使用绿色可回收催化剂 Amberlit IR-120H 树脂高效合成了一系列 2,6-二芳基哌啶-4-亚基噻唑烷-4-one 衍生物（15-21）。所有化合物均通过元素分析、FT-IR、1H、13C NMR光谱表征。该化合物的构象通过 2D NMR 光谱分析明确指定。化合物 21 的单晶 X 射线衍射记录和数据表明该化合物在空间群 Pī 的三斜晶系​​中结晶。观察到的化学位移和耦合常数表明哌啶酮环（15-21）采用椅子构象，芳基呈赤道取向。在固态下，关于 CN 双键的构型与 C-5 碳是同构的。筛选所有化合物的体外抗菌和抗分枝杆菌活性。在测试中，发现化合物 17 和 18 具有有效的抑制作用，MIC 值在 0.2–0.8 μg/mL 的范围内。通过光谱法研究了化合物与小牛胸腺DNA的相互作用，结果表明化合物通过凹槽结合模式与脱氧核糖核酸(DNA)结合。