1-苄基-2-甲基哌啶-3-酮 | 74798-56-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-苄基-2-甲基哌啶-3-酮
• 英文名称: 1-benzyl-2-methylpiperidin-3-one
• 英文别名: 1-benzyl-2-methyl-3-piperidone；N-benzyl-2-methyl-3-piperidone
• CAS: 74798-56-4
• 化学式: C₁₃H₁₇NO
• mdl: MFCD19381893
• 分子量: 203.284
• InChiKey: WYHHURGFXKJVKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苄基-2-甲基哌啶-3-酮 在 盐酸 、 红铝 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 28.0h， 生成 1-苄基吡咯烷-2-腈
  参考文献：
  名称：

  Acid-catalyzed rearrangement of 1-benzyl-2-methyl-3-piperidone to 1-benzyl-2-acetylpyrrolidine

  摘要：

  We report that 1-benzyl-2-methyl-3-piperidone, conveniently prepared from 3-hydroxy-2-methylpyridine, undergoes rearrangement to 1-benzyl-2-acetylpyrrolidine in aqueous 6 N HCl at reflux. Studies showing that the 2,2-dimethyl analog is inert under the same conditions support a mechanism of reversible tautomeric equilibria via ring-opened intermediates, one of which was independently synthesized and shown to be a kinetically competent intermediate to product. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.038
• 作为产物：
  描述：

  (3E)-1-benzyl-3-(1-iodoethylidene)-2-methylpiperidine 在 盐酸 、 正丁基锂 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-苄基-2-甲基哌啶-3-酮
  参考文献：
  名称：

  碘化物促进的醛亚胺离子炔烃环化。取代的四氢吡啶和3-亚烷基亚哌啶的方便合成。

  摘要：

  用4-炔基胺和3-炔基胺的碘化物促进的醛环化分别提供了直接合成途径获得亚烷基亚哌啶4和四氢吡啶8。

  DOI：

  10.1016/s0040-4039(00)74663-6

文献信息

• Convergent and Selective Synthesis of Pyrrolidinones, Piperidinones, Dihydropyridinones and Pyridinols from a Common Intermediate - Potential Precursors of Bioactive Products
  作者：Mouhamad Jida、Jean Ollivier

  DOI：10.1002/ejoc.200800380

  日期：2008.8

  furnish racemic pyrrolidinones as a mixture of diastereomers and piperidinones. In contrast, the synthesis of optically active dihydropyridinones was achieved through a one-pot FeCl3/AcONa reaction or performed by using bis(sym-collidine)iodine hexafluorophosphate. Furthermore, whereas the palladium-mediated hydrogenolysis of these dihydropyridinones furnished both chiral piperidinones and original pyridinols

  钛介导的天然和非天然 β-氨基酸衍生物的环丙烷化提供氮杂双环 [3.1.0] 己-1-醇作为非对映异构体的混合物，可通过硅胶色谱法分离。根据所采用的环裂解程序，这些化合物可有效地产生多种用于合成药物的中间体。因此，根据实验条件，碱性处理可以提供作为非对映异构体和哌啶酮混合物的外消旋吡咯烷酮。相比之下，光学活性二氢吡啶酮的合成是通过一锅 FeCl3/AcONa 反应实现的，或者通过使用双（sym-collidine）碘六氟磷酸盐进行的。此外，虽然钯介导的这些二氢吡啶酮的氢解提供了手性哌啶酮和原始吡啶醇，CeIV 促进的自由基过程产生手性三环哌啶酮。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Iridium-Catalyzed Selective Hydrogenation of 3-Hydroxypyridinium Salts: A Facile Synthesis of Piperidin-3-ones
  作者：Wen-Xue Huang、Bo Wu、Xiang Gao、Mu-Wang Chen、Baomin Wang、Yong-Gui Zhou

  DOI：10.1021/acs.orglett.5b00276

  日期：2015.4.3

  homogeneous iridium catalyst, providing a direct access to 2- and 4-substituted piperidin-3-one derivatives with high yields, which are important organic synthetic intermediates and the prevalent structural motifs in pharmaceutical agents. Mild reaction conditions, high chemoselectivity, and easy scalability make this reaction highly practical for the synthesis of piperidin-3-ones.

  已经使用均相铱催化剂实现了3-羟基吡啶鎓盐的选择性加氢，可以高产率直接获得2-和4-取代的哌啶-3-酮衍生物，这些衍生物是重要的有机合成中间体，并且在结构上很普遍。药剂。温和的反应条件，高的化学选择性和容易的可扩展性使该反应在合成哌啶3-3-酮中具有很高的实用性。
• Dynamic kinetic asymmetric arylation and alkenylation of ketones
  作者：Lin-Xin Ruan、Bo Sun、Jia-Ming Liu、Shi-Liang Shi

  DOI：10.1126/science.ade0760

  日期：2023.2.17

  Despite the importance of enantioenriched alcohols in medicinal chemistry, total synthesis, and materials science, the efficient and selective construction of enantioenriched tertiary alcohols bearing two contiguous stereocenters has remained a substantial challenge. We report a platform for their preparation through the enantioconvergent, nickel-catalyzed addition of organoboronates to racemic, nonactivated

  尽管富含对映体的醇在药物化学、全合成和材料科学中具有重要意义，但有效和选择性地构建具有两个相邻立构中心的富含对映体的叔醇仍然是一个巨大的挑战。我们报告了一个通过对映收敛、镍催化的有机硼酸盐加成外消旋非活化酮来制备它们的平台。我们通过芳基和烯基亲核试剂的动态动力学不对称加成，一步制备了几类重要的 α,β-手性叔醇，具有高水平的非对映选择性和对映选择性。我们应用此协议来修改几种洛芬药物并快速合成生物学相关分子。我们期望这种镍催化的，
• Iorio; Gatta; Michalek, European Journal of Medicinal Chemistry, 1980, vol. 15, # 2, p. 165 - 171
  作者：Iorio、Gatta、Michalek

  DOI：——

  日期：——
• Synthesis and α-adrenergic activity of 2- and 6-methyl-substituted (3,4-dihydroxyphenyl)-3-piperidinols
  作者：B Macchia、M Macchia、A Martinelli、E Martinotti、E Orlandini、F Romagnoli、R Scatizzi

  DOI：10.1016/s0223-5234(97)83974-8

  日期：1997.1

  Previous drug-receptor interaction mechanism studies at the molecular level of adrenergic drugs made it possible to construct two three-dimensional molecular models, A and B, using conformationally restrained cyclic analogues of natural catechol amines, including 3-(3,4-dihydroxyphenyl)-3-piperidinol (3-DPP, 3); these models offer useful information about the steric requirements for the direct activation of alpha(1)- and alpha(2)-adrenergic receptors, respectively. In order to grain further knowledge about the steric requirements of these receptors, we also synthesized 3-(3,4-dihydroxyphenyl)-c-2-methyl-r-3-piperidinol (2-MDPP, 8) and the 3-(3,4-dihydroxyphenyl)-c- and -t-6-methyl-r-3-piperidinols (6-MDPPs 9 and 10); these differ from the 3-DPP 3 used for the construction of the molecular models exclusively in the presence of a methyl in the 2 or 6 position of the heterocyclic ring. The configuration and conformation of the MDPPs 8-10 were assigned by H-1-NMR and IR studies, and confirmed by conformational analysis performed by means of theoretical calculations. The alpha(1)- and alpha(2)-adrenergic properties were evaluated in vitro both by radioligand binding assays and by functional tests on isolated preparations. The results obtained made it possible to obtain a more refined steric definition of the A and B models.