4-N,4-N-dimethyl-3-N-naphthalen-1-ylpyridine-3,4-diamine | 1381776-07-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-N,4-N-dimethyl-3-N-naphthalen-1-ylpyridine-3,4-diamine
• CAS: 1381776-07-3
• 化学式: C₁₇H₁₇N₃
• 分子量: 263.342
• InChiKey: AJYCVHFLCCICKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-萘胺 、 3-溴-4-N,N-二甲氨基吡啶 在 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以51%的产率得到4-N,4-N-dimethyl-3-N-naphthalen-1-ylpyridine-3,4-diamine
  参考文献：
  名称：

  Efficient C-3 functionalization of 4-dimethylaminopyridine (DMAP). A straightforward access to new chiral nucleophilic catalysts

  摘要：

  Herein, the straightforward C-3 functionalization of 4-dimethylaminopyridine (DMAP) backbone is disclosed. An efficient halogen-metal exchange procedure from 3-bromo DMAP 1 is reported providing a large panel of C-3 functionalized DMAPs. In addition, a Pd-catalysed C-N cross-coupling reaction is also described furnishing new 3-amino DMAPs. These new functionalization pathways led to the resolution-free synthesis of three new chiral DMAP catalysts in few steps and a good overall yield. These new catalysts were evaluated into the Steglich rearrangement giving modest enantioselectivities (up to 20% ee). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.068

文献信息

• Efficient C-3 functionalization of 4-dimethylaminopyridine (DMAP). A straightforward access to new chiral nucleophilic catalysts
  作者：Thomas Poisson、Sylvain Oudeyer、Vincent Levacher

  DOI：10.1016/j.tetlet.2012.04.068

  日期：2012.6

  Herein, the straightforward C-3 functionalization of 4-dimethylaminopyridine (DMAP) backbone is disclosed. An efficient halogen-metal exchange procedure from 3-bromo DMAP 1 is reported providing a large panel of C-3 functionalized DMAPs. In addition, a Pd-catalysed C-N cross-coupling reaction is also described furnishing new 3-amino DMAPs. These new functionalization pathways led to the resolution-free synthesis of three new chiral DMAP catalysts in few steps and a good overall yield. These new catalysts were evaluated into the Steglich rearrangement giving modest enantioselectivities (up to 20% ee). (C) 2012 Elsevier Ltd. All rights reserved.