1-(3-hydroxypropyl)-5-methylpyrrolidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-(3-hydroxypropyl)-5-methylpyrrolidin-2-one
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: CFEHSLPMLJBVQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  C₁₀H₁₉NO₃ 在 氢气 作用下， 以 neat (no solvent) 为溶剂， 85.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 1-(3-hydroxypropyl)-5-methylpyrrolidin-2-one
  参考文献：
  名称：

  在环境氢气压下AuPd纳米颗粒上乙酰丙酸乙酯的还原胺化为吡咯烷酮

  摘要：

  本文中，我们描述了一种AuPd催化剂，用于在环境压力下将乙酰丙酸乙酯（EL）和胺选择性和无溶剂转化为吡咯烷酮。优化的Au 66 Pd 34纳米颗粒催化剂稳定且可重复使用10次以上。AuPd催化作用扩展到了乙酰丙酸和4-乙酰丁酸的还原胺化反应，在较温和的条件下不仅为吡咯烷酮而且还为哌啶提供了绿色化学方法，这两者都是设计聚合物，天然产物和药物的重要支架。

  DOI：

  10.1039/c9gc00396g

文献信息

• Ambient Reductive Amination of Levulinic Acid to Pyrrolidones over Pt Nanocatalysts on Porous TiO₂ Nanosheets
  作者：Chao Xie、Jinliang Song、Haoran Wu、Yue Hu、Huizhen Liu、Zhanrong Zhang、Pei Zhang、Bingfeng Chen、Buxing Han

  DOI：10.1021/jacs.8b13024

  日期：2019.3.6

  Construction of N-substituted pyrrolidones from biomass-derived levulinic acid (LA) via reductive amination is a highly attractive route for biomass valorization. However, realizing this transformation using H2 as the hydrogen source under mild conditions is still very challenging. Herein, we designed porous TiO2 nanosheets-supported Pt nanoparticles (Pt/P-TiO2) as the heterogeneous catalyst. The prepared Pt/P-TiO2

  通过还原胺化从生物质衍生的乙酰丙酸 (LA) 构建 N 取代的吡咯烷酮是一种极具吸引力的生物质价值化途径。然而，在温和条件下使用 H2 作为氢源实现这种转化仍然非常具有挑战性。在此，我们设计了多孔 TiO2 纳米片负载的 Pt 纳米粒子（Pt/P-TiO2）作为多相催化剂。制备的 Pt/P-TiO2 在环境温度和 H2 压力下对 LA 的还原胺化非常有效，以生产各种 N-取代的吡咯烷酮（34 个实例）。同时，Pt/P-TiO2对乙酰丙酸酯、4-乙酰丁酸、2-乙酰苯甲酸和2-羧基苯甲醛的还原胺化显示出良好的适用性。
• Production of 5-mehyl-N-aryl-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive of levulinic acid esters with aryl and alkyl amines
  申请人：——

  公开号：US20040192938A1

  公开（公告）日：2004-09-30

  This invention relates to a process for producing 5-methyl-N-aryl-2-pyrrolidone, 5-methyl-N-alkyl-2-pyrrolidone, and 5-methyl-N-cycloalkyl-2-pyrrolidone by reductive amination of levulinic acid esters with aryl or alkyl amines utilizing a metal catalyst, which is optionally supported.

  这项发明涉及利用金属催化剂（可选择性地支撑）对亚苄胺或烷基胺进行脱氢胺化，以生产5-甲基-N-芳基-2-吡咯酮、5-甲基-N-烷基-2-吡咯酮和5-甲基-N-环烷基-2-吡咯酮的方法。
• Production of 5-methyl-N-aryl-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid esters with aryl and alkyl amines
  申请人：Manzer Ernest Leo

  公开号：US20050033063A1

  公开（公告）日：2005-02-10

  This invention relates to a process for producing 5-methyl-N-aryl-2-pyrrolidone, 5-methyl-N-alkyl-2-pyrrolidone, and 5-methyl-N-cycloalkyl-2-pyrrolidone by reductive amination of levulinic acid esters with aryl or alkyl amines utilizing a metal catalyst, which is optionally supported.

  本发明涉及一种生产 5-甲基-N-芳基-2-吡咯烷酮、5-甲基-N-烷基-2-吡咯烷酮和 5-甲基-N-环烷基-2-吡咯烷酮的工艺，其方法是利用一种金属催化剂，将乙酰丙酸酯与芳基或烷基胺进行还原胺化。
• Production of 5-methyl-N-aryl-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive of levulinic acid esters with aryl and alkyl amines
  申请人：Manzer Ernest Leo

  公开号：US20050137406A1

  公开（公告）日：2005-06-23

  This invention relates to a process for producing 5-methyl-N-aryl-2-pyrrolidone, 5-methyl-N-alkyl-2-pyrrolidone, and 5-methyl-N-cycloalkyl-2-pyrrolidone by reductive amination of levulinic acid esters with aryl or alkyl amines utilizing a metal catalyst, which is optionally supported.

  本发明涉及一种生产 5-甲基-N-芳基-2-吡咯烷酮、5-甲基-N-烷基-2-吡咯烷酮和 5-甲基-N-环烷基-2-吡咯烷酮的工艺，其方法是利用一种金属催化剂，将乙酰丙酸酯与芳基或烷基胺进行还原胺化。
• Chemicals from Biomass: Chemoselective Reductive Amination of Ethyl Levulinate with Amines
  作者：Juan D. Vidal、Maria J. Climent、Patricia Concepcion、Avelino Corma、Sara Iborra、Maria J. Sabater

  DOI：10.1021/acscatal.5b01113

  日期：2015.10.2

  N-substituted-5-methyl-2-piyrrolidones have been obtained by reductive amination of ethyl levulinate with amines in the presence of H-2 as reducing agent under solvent-free conditions. The process involves as a first step the formation of an imine intermediate followed by hydrogenation of the imine group and subsequent cyclization into pyrrolidone. Pt/TiO2 with Pt crystal faces decorated with TiOx is a very active and chemoselective catalyst, being possible to achieve high conversion and selectivity to the corresponding N-substituted-5-methyl-2-pyrrolidones even when other groups susceptible of hydrogenation such as vinyl, carbonyl, or cyano groups are present in the amine moiety. A kinetic study showed that the reaction-controlling step is the formation of the imine intermediate. The rate of formation is enhanced by the presence of protonic acid sites generated on the support by hydrogen dissociation on the metal, resulting in a true bifunctional catalyst for the reaction.