N²,N²'-((1R,2R)-cyclohexane-1,2-diyl)bis(N⁴,N⁴-dimethylpyridine-2,4-diamine) | 1416450-11-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N²,N²'-((1R,2R)-cyclohexane-1,2-diyl)bis(N⁴,N⁴-dimethylpyridine-2,4-diamine)
• 英文别名: 2-N-[(1R,2R)-2-[[4-(dimethylamino)pyridin-2-yl]amino]cyclohexyl]-4-N,4-N-dimethylpyridine-2,4-diamine
• CAS: 1416450-11-7
• 化学式: C₂₀H₃₀N₆
• 分子量: 354.498
• InChiKey: AKPXHIBFVFEYOO-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-溴-4-二甲基氨基吡啶 、 (1R,2R)-1,2-diaminocyclohexane 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 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 12.0h， 以56%的产率得到N²,N²'-((1R,2R)-cyclohexane-1,2-diyl)bis(N⁴,N⁴-dimethylpyridine-2,4-diamine)
  参考文献：
  名称：

  A method for the synthesis of pyridine-based C2-symmetrical chiral nucleophilic organocatalysts via Pd-catalyzed coupling

  摘要：

  A one step Pd-catalyzed coupling methodology involving a reaction between a chiral diamine and a 2-bromo-4-(alkylamino)pyridine, was developed for the synthesis of novel C-2-symmmetrical chiral compounds with chemical yields of up to 87%. The organocatalytic performance was tested as an alternative to the enzymatic kinetic resolution of 1-phenylethanol and a promising result of 76% ee was obtained. We observed that the catalysts synthesized had their own characteristics in terms of enantioselectivity; for example, non-nucleophilic heterogeneous auxiliary bases and ether solvents proved to be more efficient. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.007
• 作为试剂：
  描述：

  苏合香醇 、 乙酸酐 在 N²,N²'-((1R,2R)-cyclohexane-1,2-diyl)bis(N⁴,N⁴-dimethylpyridine-2,4-diamine) 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以8%的产率得到
  参考文献：
  名称：

  A method for the synthesis of pyridine-based C2-symmetrical chiral nucleophilic organocatalysts via Pd-catalyzed coupling

  摘要：

  A one step Pd-catalyzed coupling methodology involving a reaction between a chiral diamine and a 2-bromo-4-(alkylamino)pyridine, was developed for the synthesis of novel C-2-symmmetrical chiral compounds with chemical yields of up to 87%. The organocatalytic performance was tested as an alternative to the enzymatic kinetic resolution of 1-phenylethanol and a promising result of 76% ee was obtained. We observed that the catalysts synthesized had their own characteristics in terms of enantioselectivity; for example, non-nucleophilic heterogeneous auxiliary bases and ether solvents proved to be more efficient. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.007

文献信息

• Cu-Catalyzed Selective Mono-<i>N</i>-pyridylation: Direct Access to 2-AminoDMAP/Sulfonamides as Bifunctional Organocatalysts
  作者：Murat Isik、Cihangir Tanyeli

  DOI：10.1021/jo302713b

  日期：2013.2.15

  Direct and selective mono-N-pyridylation of trans-(R,R)-cyclohexane-1,2-diamine is described here. Facile preparation of a novel chiral 2-aminoDMAP core catalaphore via Cu catalysis has led to the development of various sulfonamide/2-aminoDMAPs as bifunctional acid/base organocatalysts (most in two steps overall), which have been shown to very effectively promote asymmetric conjugate addition of acetylacetone to trans-beta-nitroolefins with good to excellent yields (87-93%) and enantioselectivites (up to 99%).