5-methyl-N-(2-isopropylphenyl)-2-pyrrolidone

• 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: 5-methyl-N-(2-isopropylphenyl)-2-pyrrolidone
• 英文别名: 5-Methyl-1-(2-propan-2-ylphenyl)pyrrolidin-2-one
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: HHVOLRFYRXCTEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  乙酰丙酸乙酯 、 2-异丙基苯胺 在 platinum on carbon 氢气 作用下， 以 1,4-二氧六环 为溶剂， 150.0 ℃ 、6.9 MPa 条件下， 反应 8.0h， 生成 5-methyl-N-(2-isopropylphenyl)-2-pyrrolidone
  参考文献：
  名称：

  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

  摘要：

  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。

  公开号：

  US20040192938A1

文献信息

• Cu-Catalyzed C–N Coupling with Sterically Hindered Partners
  作者：Atanu Modak、Alex J. Nett、Elizabeth C. Swift、Michael C. Haibach、Vincent S. Chan、Thaddeus S. Franczyk、Shashank Shekhar、Silas P. Cook

  DOI：10.1021/acscatal.0c02965

  日期：2020.9.18

  reemerged as a viable alternative to the versatile Pd-catalyzed C–N coupling. Coupling sterically hindered reaction partners, however, remains challenging. Herein, we disclose the discovery and development of a pyrrole-ol ligand to facilitate the coupling of ortho-substituted aryl iodides with sterically hindered amines. The ligand was discovered through a library screening approach and highlights the

  铜是一种地球储量丰富的金属，已重新成为多功能 Pd 催化的 C-N 偶联的可行替代品。然而，偶联位阻反应伙伴仍然具有挑战性。在此，我们公开了吡咯醇配体的发现和开发，以促进邻位取代的芳基碘化物与空间位阻胺的偶联。该配体是通过文库筛选方法发现的，突出了挖掘富含杂原子的药物文库以寻找有用的配体基序的价值。进一步评估表明，该配体在这些具有挑战性的转化中具有独特的有效性。该反应能够偶联空间位阻伯胺和仲胺、苯胺和具有广泛官能团耐受性的酰胺。
• 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.
• 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：E.I. DUPONT DE NEMOURS AND COMPANY

  公开号：EP1605756A2

  公开（公告）日：2005-12-21