1-(3-phenylpropyl)pyrrolidine-2-carbonitrile | 1346425-05-5

• 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-(3-phenylpropyl)pyrrolidine-2-carbonitrile
• CAS: 1346425-05-5
• 化学式: C₁₄H₁₈N₂
• 分子量: 214.31
• InChiKey: IVJDMGWPGPGRRY-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：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  苯丙醛 在 2-乙基-己酸稀土盐 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 18.58h， 生成 1-(3-phenylpropyl)pyrrolidine-2-carbonitrile 、 4-phenyl-2-(pyrrolidin-1-yl)butanenitrile
  参考文献：
  名称：

  Redox-Neutral α-Cyanation of Amines

  摘要：

  alpha-Aminonitriles inaccessible by traditional Strecker chemistry are obtained in redox-neutral fashion by direct amine alpha-cyanation/N-alkylation or alternatively, alpha-aminonitrile isomerization. These unprecedented transformations are catalyzed by simple carboxylic acids.

  DOI：

  10.1021/ja308009g

文献信息

• A Highly Active System for the Metal-Free Aerobic Photocyanation of Tertiary Amines with Visible Light: Application to the Synthesis of Tetraponerines and Crispine A
  作者：Julio Cesar Orejarena Pacheco、Alexander Lipp、Alexander M. Nauth、Fabian Acke、Jule-Philipp Dietz、Till Opatz

  DOI：10.1002/chem.201504845

  日期：2016.4.4

  A highly efficient metal‐free catalytic system for the aerobic photocyanation of tertiary amines with visible light is reported. The use of air as terminal oxidant offers an improved safety profile compared with pure oxygen, the used compact fluorescent lamp (CFL) light sources are highly economical, and no halogenated solvents are required. This system not only proves to be effective for a wide variety

  报道了一种高效的无金属催化体系，用于可见光下叔胺的有氧光致氰化。与纯氧相比，使用空气作为终端氧化剂可提高安全性，所使用的紧凑型荧光灯（CFL）光源非常经济，并且不需要卤化溶剂。该系统不仅证明对多种三烷基胺，药物和生物碱有效，而且显着还使有机染料有史以来最低的催化剂负载量（0.00001 mol％或0.1 ppm）。对获得的α-氨基腈进行了Bruylants反应和C-烷基化/脱氰，以证明复杂分子的后功能化。
• The Decarboxylative Strecker Reaction
  作者：Deepankar Das、Matthew T. Richers、Longle Ma、Daniel Seidel

  DOI：10.1021/ol202957d

  日期：2011.12.16

  alpha-Amino acids react with aldehydes in the presence of a cyanide source to form alpha-amino nitriles in what can be considered a decarboxylative variant of the classical Strecker reaction. This unprecedented transformation does not require the use of a metal catalyst and provides facile access to valuable alpha-amino nitrites that are inaccessible by traditional Strecker chemistry.
• Redox-Neutral α-Cyanation of Amines
  作者：Longle Ma、Weijie Chen、Daniel Seidel

  DOI：10.1021/ja308009g

  日期：2012.9.19

  alpha-Aminonitriles inaccessible by traditional Strecker chemistry are obtained in redox-neutral fashion by direct amine alpha-cyanation/N-alkylation or alternatively, alpha-aminonitrile isomerization. These unprecedented transformations are catalyzed by simple carboxylic acids.