2,6-diphenyl-3-carboethoxypiperidin-4-one | 102012-64-6

• 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-diphenyl-3-carboethoxypiperidin-4-one
• 英文别名: 2,6-diphenyl-3-ethoxycarbonylpiperidin-4-one；3-Ethoxycarbonyl-2,6-diphenyl-piperid-4-on；3-carboxyethyl-2,6-diphenylpiperidin-4-one；4-oxo-2,6-diphenyl-piperidine-3-carboxylic acid ethyl ester；4-Oxo-2,6-diphenyl-piperidin-3-carbonsaeure-aethylester；Ethyl 4-oxo-2,6-diphenylpiperidine-3-carboxylate
• CAS: 102012-64-6
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: WVIOXDTZTOXYGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  474.6±45.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-diphenyl-3-carboethoxypiperidin-4-one 在 sodium ethanolate 、 三乙胺 作用下， 以 乙醇 、 苯 为溶剂， 反应 16.0h， 生成 6-Acetyl-2-amino-5,7-diphenyl-3,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-one
  参考文献：
  名称：

  Facile Synthesis of 2-Amino-5,6,7,8-tetrahydro-5,7-diarylpyrido[4,3-d]pyrimidin-4-ols

  摘要：

  2-Amino-5,6,7,8-tetrahydro-5,7-diarylpyrido[4,3-d]pyrimidin-4-ols were synthesized from various ethyl 2,6-diaryl-4-oxopiperidin-3-carboxylates with guanidine hydrochloride in presence of sodium ethoxide.

  DOI：

  10.1080/00397910902767491
• 作为产物：
  描述：

  2,6-diphenyl-3-carboethoxy-4-iminopiperidine 在 ammonium hydroxide 、 硫酸 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 2,6-diphenyl-3-carboethoxypiperidin-4-one
  参考文献：
  名称：

  取代的4-氨基哌啶和4-氨基四氢吡啶的合成及杀菌活性

  摘要：

  在关于哌啶衍生物杀虫活性的合成和研究的后续工作 [2] 中，我们转向制备新的取代哌啶和四氢吡啶，在 C(4) 位含有一个氨基或一个酰胺基。用盐酸处理反应混合物后，苯甲醛与乙酰乙酸酯在AcONH 存在下缩合，得到盐酸盐形式的2，6-二苯基-3-碳乙氧基-4-亚氨基哌啶(I)。氨水对盐酸盐的作用得到亚胺的烯胺形式，即取代的4-氨基-1,2,5,6-四氢吡啶(II)，其可以通过无水HCl在无水醚中转化为化合物I。这在 2,6-二苯基-3-碳乙氧基哌啶系列中建立了 4-亚氨基 4 烯胺转化。

  DOI：

  10.1007/bf00772137

文献信息

• Synthesis, crystal and antibacterial studies of diversely functionalized tetrahydropyridin-4-ol
  作者：Gopalakrishnan Aridoss、Shanmugasundaram Amirthaganesan、Yeon Tae Jeong

  DOI：10.1016/j.bmcl.2010.02.015

  日期：2010.4

  piperidin-4-one derivatives, we have synthesized two series of 3-carboxyethyl-2,6-diphenyl-4-hydroxy-Δ3-tetrahydropyridine derivatives bearing diversified heterocyclic and aromatic systems at the nitrogen atom through acetyl (6–18) and 2-propanoyl (9–31) linkers. Unlike acetyl derivatives, NMR spectral pattern of the propanoyl counterparts revealed the existence of pair of rotational isomers (syn and anti) in

  在努力扩大与哌啶-4-酮衍生物有关的抗菌活性谱，我们已经合成了两个系列的3-羧乙基-2,6-二苯基-4-羟基- Δ 3四氢吡啶衍生物轴承多样化杂环和芳族系统通过乙酰基（6 – 18）和2-丙酰基（9 – 31）接头在氮原子上连接。与乙酰基衍生物不同，丙酰基对应物的NMR光谱图显示，由于绕N-CO键的旋转受阻，室温下溶液中存在一对旋转异构体（顺式和反式）。9和24的X射线晶体研究清楚地指出，所有化合物特别是仅以一种形式存在，呈固态的稳定合成形式。筛选了每种化合物对九种人类致病性革兰氏阳性菌株（包括多种耐药菌和七种有问题的革兰氏阴性菌株）的体外抗菌活性。在本文研究的各种杂环中，咪唑取代的衍生物12和25表现出的抗菌活性接近Linezolid和Trovafloxacin药物，特别是对多种耐药性粪便肠球菌-VanA表型菌株的抗菌活性。
• One-Pot Synthesis of Substituted Piperidinones and 3,4-Dihydropyrimidinones Using a Highly Active and Recyclable Supported Ionic Liquid Phase Organocatalyst
  作者：Pankaj Sharma、Manjulla Gupta、Monika Gupta、Rajive Gupta

  DOI：10.1071/ch15133

  日期：——

  1-Ethyl-3-methylimidazolium ethyl sulfate was synthesized and its supported ionic liquid phase form was prepared and used as an organocatalyst for the synthesis of substituted piperidinones and 3,4-dihydropyrimidinones. The ionic liquid was characterized by 1H NMR, 13C NMR, and mass spectrometry. The catalyst is novel, stable, completely heterogeneous, and recyclable for several times and can be easily recovered by filtration. It was characterized with scanning electron microscopy, transmission electron microscopy, thermogravimetric analysis, and energy-dispersive X-ray spectroscopy techniques. The workup procedures are very simple, and products were obtained in good-to-excellent yields with reasonable purities without the need for further chromatographic purification.

  合成了 1-乙基-3-甲基咪唑鎓硫酸乙酯，并制备了其支撑离子液体相，将其用作合成取代哌啶酮和 3,4-二氢嘧啶酮的有机催化剂。该离子液体通过 1H NMR、13C NMR 和质谱进行了表征。该催化剂新颖、稳定、完全异构，可多次循环使用，并可通过过滤轻松回收。利用扫描电子显微镜、透射电子显微镜、热重分析和能量色散 X 射线光谱技术对其进行了表征。制备过程非常简单，无需进一步的色谱纯化，即可获得产率良好至极佳、纯度合理的产品。
• 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.
• Synthesis, spectral, crystal and antimicrobial studies of biologically potent oxime ethers of nitrogen, oxygen and sulfur heterocycles
  作者：Paramasivam Parthiban、Gopalakrishnan Aridoss、Paramasivam Rathika、Venkatachalam Ramkumar、Senthamaraikannan Kabilan

  DOI：10.1016/j.bmcl.2009.04.038

  日期：2009.6

  Three series of oxime ethers viz, 2,6-diarylpiperidin-4-one O-benzyloximes 5a-o, 2,6-diaryltetrahydropyran-4-one O-benzyloximes 7a-e and 2,6-diaryltetrahydrothiopyran-4-one O-benzyloximes 11a-b and 12a-c were synthesized and stereochemistry is established by their spectral and single crystal analysis. A SAR study has been carried out for the above oxime ethers against a panel of antibacterial (Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhi and Escherichia coli) and antifungal agents (Candida albicans, Candida-51, Rhizopus sp., Aspergillus niger, Aspergillus flavus and Cryptococcus neoformans), respectively, using Ciprofloxacin and Amphotericin B as standards. Most of the chloro/methyl/methoxy substituted compounds exerted moderate to good activity against all the tested organisms; moreover, some compounds (5i, 5l, 5n, 5o, 7c2, 7d1, 7d2, 7e, 11b and 12c) exhibited promising activity than standard drugs. (C) 2009 Elsevier Ltd. All rights reserved.
• Bhargava,P.N.; Prasad,K.U., Journal of the Indian Chemical Society, 1961, vol. 38, p. 165 - 166
  作者：Bhargava,P.N.、Prasad,K.U.

  DOI：——

  日期：——