1-(2-methoxybenzyl)-5-methylpyrrolidin-2-one | 1439402-19-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2-methoxybenzyl)-5-methylpyrrolidin-2-one
• 英文别名: 1-[(2-Methoxyphenyl)methyl]-5-methylpyrrolidin-2-one
• CAS: 1439402-19-3
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: SQYGUNVVNPJJCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻甲氧基苄胺 、 乙酰丙酸 在 甲酸 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以91%的产率得到1-(2-methoxybenzyl)-5-methylpyrrolidin-2-one
  参考文献：
  名称：

  Catalyst-free transformation of levulinic acid into pyrrolidinones with formic acid

  摘要：

  在无催化剂的情况下，通过二甲基亚砜中的甲酸，将乙酰乙酸（LA）转化为吡咯烷酮类化合物。机理研究表明，反应涉及一个亚胺中间体和一个限速的氢负离子转移步骤。

  DOI：

  10.1039/c3gc42125b

文献信息

• Highly efficient transformation of levulinic acid into pyrrolidinones by iridium catalysed transfer hydrogenation
  作者：Yawen Wei、Chao Wang、Xue Jiang、Dong Xue、Jia Li、Jianliang Xiao

  DOI：10.1039/c3cc41661e

  日期：——

  Levulinic acid (LA) is transformed into pyrrolidinones via iridium-catalysed reductive amination using formic acid as the hydrogen source under aqueous conditions. The catalytic system is the most active and performs under the mildest conditions ever reported for the reductive amination of LA.

  月桂酸（LA）在水相条件下，通过使用甲酸作为氢源、在铱催化下进行还原胺化反应，转化为吡咯烷酮。该催化体系是目前为止报道的最具活性的，在所有已知的月桂酸还原胺化反应中最温和条件下进行的催化系统。
• One-Pot, Tandem Reductive Amination/Alkylation–Cycloamidation for Lactam Synthesis from Keto or Amino Acids
  作者：P. Veeraraghavan Ramachandran、Shivani Choudhary

  DOI：10.1021/acs.joc.3c01126

  日期：2023.11.17

  Monotrifluoroacetoxyborane-amines, prepared by treating borane-amines with trifluoroacetic acid, have been shown to be efficient reagents for a one-pot, tandem reductive amination/alkylation–cycloamidation of keto or amino acids to achieve the synthesis of 5-aryl or 5-methyl pyrrolidin-2-ones and 6-aryl or 6-methyl piperidin-2-ones.

  通过用三氟乙酸处理硼烷胺制备的单三氟乙酰氧基硼烷胺已被证明是酮或氨基酸的一锅串联还原胺化/烷基化-环酰胺化以实现 5-芳基或 5- 合成的有效试剂。甲基吡咯烷-2-酮和6-芳基或6-甲基哌啶-2-酮。
• Heterogeneous Pt Catalysts for Reductive Amination of Levulinic Acid to Pyrrolidones
  作者：Abeda Sultana Touchy、S. M. A. Hakim Siddiki、Kenichi Kon、Ken-ichi Shimizu

  DOI：10.1021/cs500757k

  日期：2014.9.5

  Supported platinum catalysts have been studied for the reductive amination of levulinic acid (LA) by H-2 to N-alkyl-5-methyl-2-pyrrolidones under solvent-free conditions. The activity depends on the type of metal (Pt, Re, Pd, Rh, Ru, Cu, Ni), support material, and coloaded oxides of transition metals (V, Cr, Mo, W, Re). In 24 kinds of catalyst tested, Pt and MoOx (molybdenum oxide) coloaded TiO2 (Pt-MoOx/TiO2) shows the highest activity. Pt-MoOx/TiO2 is effective for reductive amination of LA with wide varieties of amines under mild conditions (3 bar of H-2, 100 degrees C, solvent-free) to give high isolated yield of pyrrolidinones and shows higher turnover number (TON) than previously reported catalysts for reductive amination of LA with an aliphatic amine. The catalyst can be separated from the reaction mixture by filtration, and the recovered catalyst can be reused. This is the first general and reusable heterogeneous catalytic system for the reductive amination of LA. On the basis of mechanistic studies, high activity of Pt-MoOx/TiO2 can be attributed to acid-base interaction between the add sites of Pt-MoOx/TiO2 and carboxyl groups in LA and an intermediate.