(1R,2R)-1-N,2-N-双(4-硝基苯基)环己烷-1,2-二胺 | 71603-18-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (1R,2R)-1-N,2-N-双(4-硝基苯基)环己烷-1,2-二胺
• 英文名称: N,N'-bis(4-nitrophenyl)-(1R,2R)-diaminocyclohexane
• 英文别名: (R)-trans-N.N'-Di(p-nitrophenyl)-1.2-cyclohexandiamin；trans-(1R,2R)-N,N'-bis-(4-nitrophenyl)cyclohexane-1,2-diamine；(1R,2R)-N~1~,N~2~-Bis(4-nitrophenyl)cyclohexane-1,2-diamine；(1R,2R)-1-N,2-N-bis(4-nitrophenyl)cyclohexane-1,2-diamine
• CAS: 71603-18-4
• 化学式: C₁₈H₂₀N₄O₄
• 分子量: 356.381
• InChiKey: MQEOKKPDURJGAL-QZTJIDSGSA-N

物化性质

• 熔点：
  204-206 °C
• 沸点：
  587.6±50.0 °C(Predicted)
• 密度：
  1.370±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-溴-4-硝基苯 、 (1R,2R)-1,2-diaminocyclohexane 在 potassium phosphate 、 copper(I) bromide 、 S-1,1'-联-2-萘酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以49%的产率得到(1R,2R)-1-N,2-N-双(4-硝基苯基)环己烷-1,2-二胺
  参考文献：
  名称：

  Copper(I) catalysis: Synthesis of N,N′-diarylated and N-aryl,N′-formylated chiral C2-symmetric diamines

  摘要：

  Chiral N,N'-diaryl C-2-symmetric diamines and N-aryl, N'-formyl-trans-(1R,2R)-diaminocyclohexane are readily accessed by copper catalyzed N,N'-diarylation and N-aryl,N'-formylation of trans-(1R,2R)-diaminocyclohexane with aryl bromides. N, N'-diarylation using (R)-1,1'- binaphthyl-2,2'-diamine and iodobenzene gave the corresponding (R)-N,N'-diphenyl-1,1'-binaphthyl-2,2'-diamine derivative in 83% yield. (C) 2009 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.08.002

文献信息

• Helical Superstructures of aC2-Symmetric Molecule Exhibiting Strong Second Harmonic Generation in the Solid-State
  作者：P. Gangopadhyay、T. P. Radhakrishnan

  DOI：10.1002/1521-3773(20010702)40:13<2451::aid-anie2451>3.0.co;2-m

  日期：2001.7.2

  The crystallization solvent exerts a critical control of the nonlinear optical properties of helical superstructures in molecular crystals based on N,N'-bis(4-nitrophenyl)-(1R,2R)-diaminocyclohexane. While crystallization from ethyl acetate resulted in mutually orthogonal helices with different handedness, crystallization from ethyl acetate/hexane or acetyl acetone/hexane resulted in the formation of helical motifs of a single-handedness oriented in one direction. The latter showed a strong solid-state second harmonic generation capability.
• Copper(I) catalysis: Synthesis of N,N′-diarylated and N-aryl,N′-formylated chiral C2-symmetric diamines
  作者：Laxhmaiah Alakonda、Mariappan Periasamy

  DOI：10.1016/j.jorganchem.2009.08.002

  日期：2009.11

  Chiral N,N'-diaryl C-2-symmetric diamines and N-aryl, N'-formyl-trans-(1R,2R)-diaminocyclohexane are readily accessed by copper catalyzed N,N'-diarylation and N-aryl,N'-formylation of trans-(1R,2R)-diaminocyclohexane with aryl bromides. N, N'-diarylation using (R)-1,1'- binaphthyl-2,2'-diamine and iodobenzene gave the corresponding (R)-N,N'-diphenyl-1,1'-binaphthyl-2,2'-diamine derivative in 83% yield. (C) 2009 Elsevier B. V. All rights reserved.