(2S*,3R*,6R*)-2-(hydroxymethyl)-3-methyl-6-phenyl-4-piperidone

• 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: (2S*,3R*,6R*)-2-(hydroxymethyl)-3-methyl-6-phenyl-4-piperidone
• 英文别名: (2R,3S,6S)-2-(hydroxymethyl)-3-methyl-6-phenylpiperidin-4-one
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: WLTCWFWCYXHZAD-DLOVCJGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S*,3R*,6R*)-2-(hydroxymethyl)-3-methyl-6-phenyl-4-piperidone 在 吡啶 、 咪唑 、 盐酸 、 jones reagent 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 6.0h， 生成 (2R,3S,6S)-3-Methyl-4-oxo-6-phenyl-piperidine-1,2-dicarboxylic acid 1-(2,2,2-trichloro-ethyl) ester
  参考文献：
  名称：

  Enantioselective Synthesis of Substituted Pipecolic Acid Derivatives

  摘要：

  Enantiomerically pure 4-piperidones, prepared by asymmetric [4 + 2] Diels-Alder cycloadditon of chiral 2-aminodienes with imines, have been used as starting materials for the synthesis of several derivatives of pipecolic acid. The alpha-amino acid moiety is obtained after the oxidation of a hydroxy group or a furan ring of a conveniently protected 2-aryl-6-(hydroxymethyl)-4-piperidone. Depending on the starting piperidone and the synthetic strategy, it is possible to obtain D- or L-functionalized pipecolic acid derivatives by a short synthetic procedure. Moreover, a stereoselective epimerization of the alpha-carbon atom of a particular pipecolate allows for the preparation of both cis- and trans-6-(hydroxymethyl)pipecolic acids, structures related with dipeptide isosteres.

  DOI：

  10.1021/jo9722414
• 作为产物：
  描述：

  tert-butyl-[(2E)-4-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-3-methylpenta-2,4-dienoxy]-dimethylsilane 在 盐酸 、 sodium hexamethyldisilazane 、 碳酸氢钠 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 8.0h， 生成 (2S*,3R*,6R*)-2-(hydroxymethyl)-3-methyl-6-phenyl-4-piperidone
  参考文献：
  名称：

  Barluenga, Jose; Aznar, Fernando; Ribas, Cristina, Chemistry - A European Journal, 1996, vol. 2, # 7, p. 805 - 811

  摘要：

  DOI：

文献信息

• NMR spectroscopic analysis of new spiro-piperidylrifamycins
  作者：Eduardo Rubio、Isabel Merino、Ana-Belén García、María-Paz Cabal、Cristina Ribas、Miguel Bayod-Jasanada

  DOI：10.1002/mrc.1545

  日期：2005.4

  New spiro‐piperidylrifamycin derivatives are presented. These compounds were synthesized from the reaction of 3‐amino‐4‐iminorifamycin S and enantiomerically pure 4‐piperidones, which generate diasteroisomeric rifabutin analogues with a new stereocentre at the spiranic carbon. The 1H and 13C NMR spectra of these new compounds, and also the configuration of the new stereogenic centres, were assigned

  提出了新的螺哌啶基利福霉素衍生物。这些化合物是由 3-氨基-4-亚氨基利福霉素 S 和对映异构纯 4-哌啶酮反应合成的，后者产生非对映异构的利福布汀类似物，在螺碳上有一个新的立体中心。这些新化合物的 1H 和 13C NMR 光谱，以及新立体中心的构型，都使用 2D NMR 光谱技术进行了分配。还对起始化合物利福霉素 S、3-氨基-4-亚氨基利福霉素 S 和相关利福布汀的 1H 和 13C NMR 光谱进行了初步研究，结果，它们先前公布的 13C NMR 数据得到了修正。版权所有 © 2005 John Wiley & Sons, Ltd.
• Stereoselective synthesis of 4-piperidone and 4-aminotetrahydropyridine derivatives by the imino Diels-Alder reaction of 2-amino-1,3-butadienes
  作者：Jose Barluenga、Fernando Aznar、Carlos Valdes、Maria Paz Cabal

  DOI：10.1021/jo00064a030

  日期：1993.6

  2-Amino-4-(alkoxymethyl)-1,3-butadienes react smoothly with nonactivated aldimines derived from aromatic aldehydes in the presence of ZnCl2 as Lewis acid giving rise, with good yields and very high stereoselectivity, to substituted 4-aminotetrahydropyridines which upon hydrolysis yield 4-piperidone derivatives. Moreover, the stereochemistry of the cyclization process depends on the nature of the N-substituent of the imine.
• 2-Amino-1,3-butadienes as chiral building blocks: enantioselective synthesis of 4-piperidones, 4-nitrocyclohexanones, and 1,3-cycloheptadione derivatives
  作者：Jose Barluenga、Fernando Aznar、Carlos Valdes、Alfredo Martin、Santiago Garcia-Granda、Eduardo Martin

  DOI：10.1021/ja00063a085

  日期：1993.5
• SPIROPIPERIDYL RIFAMYCINS FOR THE TREATMENT OF MICROBACTERIAL INFECTIONS
  申请人：UNIVERSIDAD DE OVIEDO

  公开号：EP1783129B1

  公开（公告）日：2010-10-13
• Spiropiperidylrifamycins for the Treatment of Mycobacterial Infections
  申请人：Barluenga Mur Jose

  公开号：US20070225266A1

  公开（公告）日：2007-09-27

  The compounds of formula (1), their pharmaceutically acceptable salts and their solvates, wherein R 1 is a radical selected between hydrogen and alkyl; R 2 is selected from hydroxyalkyl, phenyl, phenyl mono-substituted and phenyl di-substituted in positions 3 and 4; R 3 is selected from phenyl, phenyl mono-substituted and phenyl di-substituted in positions 3 and 4; the substituents of the phenyl of R 2 and R 3 selected from halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxyl and R 4 is selected from hydrogen, alkyl allyl and homoallyl, they are useful for the treatment of mycobacterial infections, in particular for the treatment of infections produced by Mycobacterium tuberculosis, Mycobacterium avium - intracellulare complex or Mycobacterium kansasii .