N-benzyl-3-(cyanomethyl)-4-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-3-(cyanomethyl)-4-methylenepyrrolidine
• 英文别名: (1-Benzyl-4-methylene-3-pyrrolidinyl)acetonitrile；2-(1-benzyl-4-methylidenepyrrolidin-3-yl)acetonitrile
• 化学式: C₁₄H₁₆N₂
• 分子量: 212.294
• InChiKey: GCQCGSUKGOPRFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  triethylsilylcyanide 、 N-benzyl-N-(2-bromo-2-propen-1-yl)-N-(2-propen-1-yl)amine 在 2,2'-联吡啶 、 bis(1,5-cyclooctadiene)nickel (0) 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以38%的产率得到N-benzyl-3-(cyanomethyl)-4-methylenepyrrolidine
  参考文献：
  名称：

  A catalytic version of a nickel promoted intramolecular tandem cyclization-cyanation process

  摘要：

  A catalytic version of the intramolecular Ni-promoted tandem cyclization-cyanation process is described. Generally, the reaction leads to mixtures of cyclic and open chain adducts in moderate to good yields. The presence of external bidendate nitrogen ligands, although not essential for the reaction outcome, provides stability to the catalytic system. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)80111-7

文献信息

• 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.
• Intramolecular Nitrogen Assistance in the Nickel-Promoted Tandem Cyclization-Capture of Amino-Tethered Vinyl Bromides and Alkenes
  作者：Daniel Sole、Yolanda Cancho、Amadeu Llebaria、Josep M. Moreto、Antonio Delgado

  DOI：10.1021/ja00105a096

  日期：1994.12
• A catalytic version of a nickel promoted intramolecular tandem cyclization-cyanation process
  作者：Susana Hinojosa、Antonio Delgado、Amadeu Llebaria

  DOI：10.1016/s0040-4039(99)80111-7

  日期：1999.1

  A catalytic version of the intramolecular Ni-promoted tandem cyclization-cyanation process is described. Generally, the reaction leads to mixtures of cyclic and open chain adducts in moderate to good yields. The presence of external bidendate nitrogen ligands, although not essential for the reaction outcome, provides stability to the catalytic system. (C) 1999 Elsevier Science Ltd. All rights reserved.