1-benzyl-3,5-dimethyl-2-iso-propyl-1,2-dihydropyridine | 1016970-54-9

• 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-3,5-dimethyl-2-iso-propyl-1,2-dihydropyridine
• 英文别名: 1-benzyl-2-isopropyl-3,5-dimethyl-1,2-dihydropyridine；1-benzyl-3,5-dimethyl-2-propan-2-yl-2H-pyridine
• CAS: 1016970-54-9
• 化学式: C₁₇H₂₃N
• 分子量: 241.376
• InChiKey: KZTWCZBJPVLJLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  1-benzyl-3,5-dimethyl-2-iso-propyl-1,2-dihydropyridine 在 palladium on activated charcoal air 、 氢气 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以62 mg的产率得到2-异丙基-3,5-二甲基吡啶
  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：

  (E)-N-benzyl-2-methylprop-2-en-1-imine 、 甲基異丙基乙炔 在 [RhCl(coe)2]2 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以100%的产率得到1-benzyl-3,5-dimethyl-2-iso-propyl-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

• Synthesis of Isoquinuclidines from Highly Substituted Dihydropyridines via the Diels–Alder Reaction
  作者：Rhia M. Martin、Robert G. Bergman、Jonathan A. Ellman

  DOI：10.1021/ol303040r

  日期：2013.2.1

  A stereo- and regioselective Diels–Alder reaction for the synthesis of highly substituted isoquinuclidines from dihydropyridines and electron-deficient alkenes has been developed. While reactions with activated dienophiles proceed readily under thermal conditions, the use of Lewis acid additives is necessary to facilitate cycloadditions for less reactive alkenes. This procedure affords the target compounds

  已经开发出立体和区域选择性 Diels-Alder 反应，用于从二氢吡啶和缺电子烯烃合成高度取代的异奎宁环。虽然与活化的亲二烯体的反应在热条件下很容易进行，但必须使用路易斯酸添加剂来促进反应性较低的烯烃的环加成。该程序以高产率和非对映选择性提供目标化合物。