1-cyclopropyl-5-methylpyrrolidin-2-one | 1351473-78-3

• 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-cyclopropyl-5-methylpyrrolidin-2-one
• CAS: 1351473-78-3
• 化学式: C₈H₁₃NO
• 分子量: 139.197
• InChiKey: IYJJISYGHSVDPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  乙酰丙酸 、 环丙胺 在 甲酸 、 C₂₄H₂₂N₄*BF₄^(1-)*Ru⁽²⁺⁾*Cl^(1-)*C₁₀H₁₄ 作用下， 以 neat (no solvent) 为溶剂， 反应 24.0h， 生成 1-cyclopropyl-5-methylpyrrolidin-2-one
  参考文献：
  名称：

  基于NHC的配位聚合物作为固体分子催化剂，用于生物量戊酸的还原胺化

  摘要：

  通过对苯撑桥联的双苯并咪唑鎓盐与选定的金属前体进行自组装，很容易制造出一类坚固的基于NHC的固体分子催化剂。其中，NHC-Ru聚合物表现出高催化活性。

  DOI：

  10.1039/c6gc02591a

文献信息

• Ruthenium-Catalyzed Conversion of Levulinic Acid to Pyrrolidines by Reductive Amination
  作者：Yao-Bing Huang、Jian-Jun Dai、Xiao-Jian Deng、Yan-Chao Qu、Qing-Xiang Guo、Yao Fu

  DOI：10.1002/cssc.201100344

  日期：2011.11.18

  Combo deal: An aqueous solution of levulinic acid (LA) and formic acid (FA) derived from biomass‐based carbohydrates can be converted efficiently to pyrrolidines via a ruthenium catalyst without need for an energy‐intensive separation of LA or an external H2 source. The ruthenium catalyst combines two processes: decomposition of FA to H2 and reductive amination of LA with an amine.

  组合交易：源自生物质基碳水化合物的乙酰丙酸（LA）和甲酸（FA）水溶液可通过钌催化剂高效转化为吡咯烷，而无需对LA或外部H 2源进行能源密集型分离。钌催化剂结合了两个过程：将FA分解为H 2和将LA与胺进行还原胺化。
• 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.