N-benzyl-4-(2-oxopropyl)-3-methylenepyrrolidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-4-(2-oxopropyl)-3-methylenepyrrolidine
• 英文别名: 1-(1-Benzyl-4-methylidenepyrrolidin-3-yl)propan-2-one
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: ATASZXGCTXFXHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙酰氯 、 N-benzyl-N-(2-bromo-2-propen-1-yl)-N-(2-propen-1-yl)amine 在 bis(1,5-cyclooctadiene)nickel (0) 、 三乙胺 作用下， 以 乙腈 为溶剂， 以30%的产率得到N-benzyl-4-(2-oxopropyl)-3-methylenepyrrolidine
  参考文献：
  名称：

  Nitrogen Assistance in Intramolecular Nickel-Promoted Tandem Cyclization−Quenching Processes

  摘要：

  A diastereoselective and mild cyclization-quenching process based on the treatment of nitrogen-tethered halodienes with stoichiometric Ni(COD)(2) is described. The success of this methodology relies on the presence of a distal amino group capable of coordinating with the metal in the transient vinyl or alkylnickel species, thus controlling the diastereoselectivity of the cyclization step and preventing Ni-H beta-elimination prior to the quenching, In general, better results are obtained in cyclizations taking place via a 5-exo-trig process, and a diversity of mono- and bicyclic nitrogenated systems are afforded in high yields by the proper choice of starting halodienes and quenching reagents, The presence of 2,2'-bipyridine as a ligand results in an acceleration of the process, and in some cases, higher diastereoselectivities and/or supression of the Ni-H beta-elimination are observed.

  DOI：

  10.1021/jo960677y

文献信息

• Synthesis of cyclopentanoids via enyne cycloaddition reaction using methylmanganese carbonyl complex
  作者：Joo Eun Lee、Soon Hyeok Hong、Young Keun Chung

  DOI：10.1016/s0040-4039(97)00168-8

  日期：1997.3

  transformation of enynes to cyclopropanated bicyclic compounds and cyclopentanes bearing an exocyclic double bond has been carried out. Control of the product distribution can be achieved by changing reaction conditions.

  已经进行了由甲基锰五羰基介导的烯炔向环丙烷化的双环化合物和带有环外双键的环戊烷的转化。可以通过改变反应条件来控制产物分布。
• Nitrogen Assistance in Intramolecular Nickel-Promoted Tandem Cyclization−Quenching Processes
  作者：Daniel Solé、Yolanda Cancho、Amadeu Llebaria、Josep M. Moretó、Antonio Delgado

  DOI：10.1021/jo960677y

  日期：1996.1.1

  A diastereoselective and mild cyclization-quenching process based on the treatment of nitrogen-tethered halodienes with stoichiometric Ni(COD)(2) is described. The success of this methodology relies on the presence of a distal amino group capable of coordinating with the metal in the transient vinyl or alkylnickel species, thus controlling the diastereoselectivity of the cyclization step and preventing Ni-H beta-elimination prior to the quenching, In general, better results are obtained in cyclizations taking place via a 5-exo-trig process, and a diversity of mono- and bicyclic nitrogenated systems are afforded in high yields by the proper choice of starting halodienes and quenching reagents, The presence of 2,2'-bipyridine as a ligand results in an acceleration of the process, and in some cases, higher diastereoselectivities and/or supression of the Ni-H beta-elimination are observed.