N-benzyl-2,3-diethyl-4,5-dimethyl-1,2-dihydropyridine | 1016970-58-3

• 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-2,3-diethyl-4,5-dimethyl-1,2-dihydropyridine
• 英文别名: 1-benzyl-2,3-diethyl-4,5-dimethyl-2H-pyridine
• CAS: 1016970-58-3
• 化学式: C₁₈H₂₅N
• 分子量: 255.403
• InChiKey: VGIZPEGLHFWGSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-2,3-diethyl-4,5-dimethyl-1,2-dihydropyridine 在 palladium on activated charcoal air 、 氢气 作用下， 以 2,2,2-三氟乙醇 、 甲苯 为溶剂， 反应 20.0h， 以59 mg的产率得到2,3-二乙基-4,5-二甲基吡啶
  参考文献：
  名称：

  Synthesis of Dihydropyridines and Pyridines from Imines and Alkynes via C−H Activation

  摘要：

  A convenient one-pot C-H alkenylation/electrocyclization/aromatization sequence has been developed for the synthesis of highly substituted pyridine derivatives from alkynes and alpha,beta-unsaturated N-benzyl aldimines and ketimines that proceeds through dihydropyridine intermediates. A new class of ligands for C-H activation was developed, providing broader scope for the alkenylation step than could be achieved with previously reported ligands. Substantial information was obtained about the mechanism of the reaction. This included the isolation of a C-H activated complex and its structure determination by X-ray analysis; in addition, kinetic simulations using the Copasi software were employed to determine rate constants for this transformation, implicating facile C-H oxidative addition and slow reductive elimination steps.

  DOI：

  10.1021/ja7104784
• 作为产物：
  描述：

  3-己炔 、 (E)-N-((E)-2-methylbut-2-en-1-ylidene)-1-phenylmethanamine 在 [RhCl(coe)2]2 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以88%的产率得到N-benzyl-2,3-diethyl-4,5-dimethyl-1,2-dihydropyridine
  参考文献：
  名称：

  Synthesis of Dihydropyridines and Pyridines from Imines and Alkynes via C−H Activation

  摘要：

  A convenient one-pot C-H alkenylation/electrocyclization/aromatization sequence has been developed for the synthesis of highly substituted pyridine derivatives from alkynes and alpha,beta-unsaturated N-benzyl aldimines and ketimines that proceeds through dihydropyridine intermediates. A new class of ligands for C-H activation was developed, providing broader scope for the alkenylation step than could be achieved with previously reported ligands. Substantial information was obtained about the mechanism of the reaction. This included the isolation of a C-H activated complex and its structure determination by X-ray analysis; in addition, kinetic simulations using the Copasi software were employed to determine rate constants for this transformation, implicating facile C-H oxidative addition and slow reductive elimination steps.

  DOI：

  10.1021/ja7104784

文献信息

• Regio- and Stereoselective 1,2-Dihydropyridine Alkylation/Addition Sequence for the Synthesis of Piperidines with Quaternary Centers
  作者：Simon Duttwyler、Shuming Chen、Colin Lu、Brandon Q. Mercado、Robert G. Bergman、Jonathan A. Ellman

  DOI：10.1002/anie.201310517

  日期：2014.4.7

  example of C alkylation of 1,2‐dihydropyridines with alkyl triflates and Michael acceptors was developed to introduce quaternary carbon centers with high regio‐ and diastereoselectivity. Hydride or carbon nucleophile addition to the resultant iminium ion also proceeded with high diastereoselectivity. Carbon nucleophile addition results in an unprecedented level of substitution to provide piperidine rings

  开发了 1,​​2-二氢吡啶与烷基三氟甲磺酸酯和迈克尔受体的 C 烷基化的第一个例子，以引入具有高区域选择性和非对映选择性的季碳中心。氢化物或碳亲核试剂加成到所得亚胺离子也具有高非对映选择性。碳亲核试剂加成导致前所未有的取代水平，以提供具有相邻四取代碳原子的哌啶环。