1-Benzyl-3,4-dimethylenepyrrolidine | 50586-30-6

• 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: 1-Benzyl-3,4-dimethylenepyrrolidine
• 英文别名: 1-Benzyl-3,4-dimethylidenepyrrolidine
• CAS: 50586-30-6
• 化学式: C₁₃H₁₅N
• 分子量: 185.269
• InChiKey: BIKUWYDBBIGYMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N,N-bis(2-chloro-2-propenyl)benzylamine 在 (Ph₃P)4NiCl₂ 作用下， 以 二甲基亚砜 为溶剂， 以54%的产率得到1-Benzyl-3,4-dimethylenepyrrolidine
  参考文献：
  名称：

  Electrocatalytic coupling of aryl halides with (1,2-bis(di-2-propylphosphino)benzene)nickel(0)

  摘要：

  Dibromo- and dichloro(1,2-bis(di-2-propylphosphino)benzene)nickel(II) is compared with tetrakis(triphenylphosphino)nickel(II) as an electrocatalyst for the reductive coupling of aryl halides. In many of the reactions examined, dehalogenation of the substrate predominated over coupling; however, preparative yields of biphenyls as high as 96% can be obtained with aryl chlorides and 2 mol % of the title catalyst in polar, coordinating solvents. Experimental factors governing the efficiency of these reactions are discussed, and possible mechanisms for coupling and catalyst deactivation are considered. Much better selectivity for aryl chlorides is attained in electroreductive couplings catalyzed by the title compound, whereas electrocatalysis with (Ph3P)4NiCl2 allows for selective intra- and intermolecular coupling at aryl bromide and vinyl chloride sites. Modest yields of cyclization products can be attained with either electrocatalyst in the presence of appropriately functionalized aryl or vinyl halides.

  DOI：

  10.1021/jo00010a014

文献信息

• Intramolecular Heck-type reactions in aqueous medium. Dramatic change in regioselectivity
  作者：Sandrine Lemaire-Audoire、Monique Savignac、Christophe Dupuis、Jean-Pierre Genêt

  DOI：10.1016/0040-4039(96)00253-5

  日期：1996.3

  Efficient intramolecular Heck-type cyclizations were carried out in aqueous medium using water-soluble Pd/TPPTS catalysts. Under these conditions, the generally observed exo process was reversed in favor of the regioselective formation of endo cyclized compounds.

  使用水溶性Pd / TPPTS催化剂在水性介质中进行高效的分子内Heck型环化反应。在这些条件下，通常观察到的外切过程被逆转，有利于内环化化合物的区域选择性形成。
• Zirconium-Mediated Intramolecular Coupling of Terminal Alkynes and Their Subsequent Carbonylation: Novel Synthesis of Seven- and Eight-Membered Heterocycles
  作者：José Barluenga、Roberto Sanz、Francisco J. Fañanás

  DOI：10.1002/chem.19970030820

  日期：1997.8

  AbstractThe development of a new method for the intramolecular coupling of terminal alkynes and for the synthesis of seven‐ and eight‐membered benzoheterocycles is reported. The key steps involve the generation of zirconocene‐alkyne complexes from 2‐bromoalkenes and the subsequent intramolecular carbometalation of olefins or acetylides. The 8‐unsubstituted zirconabicyclopentenes were carbonylated to afford unexpected products and allow access to polyfunctionalized molecules from simple starting materials.
• FOX, MARYE ANNE;CHANDLER, DANIEL A.;LEE, CHANGJIN, J. ORG. CHEM., 56,(1991) N0, C. 3246-3255
  作者：FOX, MARYE ANNE、CHANDLER, DANIEL A.、LEE, CHANGJIN

  DOI：——

  日期：——
• Electrocatalytic coupling of aryl halides with (1,2-bis(di-2-propylphosphino)benzene)nickel(0)
  作者：Marye Anne Fox、Daniel A. Chandler、Changjin Lee

  DOI：10.1021/jo00010a014

  日期：1991.5

  Dibromo- and dichloro(1,2-bis(di-2-propylphosphino)benzene)nickel(II) is compared with tetrakis(triphenylphosphino)nickel(II) as an electrocatalyst for the reductive coupling of aryl halides. In many of the reactions examined, dehalogenation of the substrate predominated over coupling; however, preparative yields of biphenyls as high as 96% can be obtained with aryl chlorides and 2 mol % of the title catalyst in polar, coordinating solvents. Experimental factors governing the efficiency of these reactions are discussed, and possible mechanisms for coupling and catalyst deactivation are considered. Much better selectivity for aryl chlorides is attained in electroreductive couplings catalyzed by the title compound, whereas electrocatalysis with (Ph3P)4NiCl2 allows for selective intra- and intermolecular coupling at aryl bromide and vinyl chloride sites. Modest yields of cyclization products can be attained with either electrocatalyst in the presence of appropriately functionalized aryl or vinyl halides.