N-cyclohexyl-3-nitrobenzenamine | 121086-17-7

• 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-cyclohexyl-3-nitrobenzenamine
• 英文别名: N-cyclohexyl-m-nitroaniline；N-cyclohexyl-3-nitroaniline；cyclohexyl(3-nitrophenyl)amine
• CAS: 121086-17-7
• 化学式: C₁₂H₁₆N₂O₂
• mdl: MFCD00997209
• 分子量: 220.271
• InChiKey: AMWRAALWQRUDKH-UHFFFAOYSA-N

物化性质

• 熔点：
  75-78 °C
• 沸点：
  365.6±25.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-碘-3-硝基苯 、 环己胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以56%的产率得到N-cyclohexyl-3-nitrobenzenamine
  参考文献：
  名称：

  CuI与聚苯胺纳米纤维结合催化形成CN键

  摘要：

  聚苯胺纳米纤维作为负载碘化亚铜催化剂 (CuI-PANInf) 的大配体已被开发用于在环境条件 (80 °C) 下将芳基卤化物（包括芳基氯化物）与脂肪族、芳香族和 N(H)-杂环胺偶联用于芳基氯化物）已被开发。这种简单有效的偶联反应方法通用性强，使用方便，而且催化剂可以多次循环使用，产率从优到优。

  DOI：

  10.1002/ejoc.201000149

文献信息

• Iron/Copper-Cocatalyzed Ullmann N,O-Arylation Using FeCl₃, CuO, and <i>rac</i>-1,1′-Binaphthyl-2,2′-diol
  作者：Hua Fu、Zhe Wang、Yuyang Jiang、Yufen Zhao

  DOI：10.1055/s-2008-1078214

  日期：——

  We have developed an efficient and inexpensive bimetallic catalyst FeCl3, CuO, and rac-BINOL that could promote N,O-arylation of aliphatic, arylamines, and phenols. The cross-coupling reaction conditions have high tolerance of various functional groups. This versatile and efficient iron/copper-cocatalyst can widely be used in the synthesis of the compounds containing ­(aryl)C-N or (aryl)C-O(aryl) bond.

  我们开发了一种高效且廉价的双金属催化剂FeCl3、CuO和rac-BINOL，可促进脂肪族、芳香胺和酚的N,O-芳基化反应。该交叉偶联反应条件对各种功能团具有良好的耐受性。这种多功能且高效的铁/铜协同催化剂可以广泛应用于含有(芳基)C-N或(芳基)C-O(芳基)键的化合物合成中。
• Two Component Recyclable Heterogeneous Catalyst, Process for Preparation Thereof and its Use for Preparation of Amines
  申请人：Likhar Pravin R.

  公开号：US20110313158A1

  公开（公告）日：2011-12-22

  The invention describes the development of highly efficient, recyclable two component system, CuAl-hydrotalcite/rac 1,1′-Binaphthalene-2,2′-diol catalytic system for the N-alkylation of electron deficient aryl chlorides in presence of potassium carbonate as a base at room temperature in 3-6 h, wherein the process is provided for the preparation of various secondary amines via C—N coupling reaction of aliphatic amines(aliphatic open chain, acyclic, benzyl amines and heterocyclic amines) with various aryl chlorides.

  该发明描述了开发高效、可回收的两组分体系，CuAl-水滑石/rac 1,1′-联萘-2,2′-二酚催化系统，用于在室温下在3-6小时内以碳酸钾为碱催化芳基氯化物的N-烷基化反应，其中该过程提供了通过脂肪胺（脂肪开链、无环、苄胺和杂环胺）与各种芳基氯化物进行C—N偶联反应制备各种二级胺的方法。
• CuI Nanoparticles for C−N and C−O Cross Coupling of Heterocyclic Amines and Phenols with Chlorobenzenes
  作者：B. Sreedhar、R. Arundhathi、P. Linga Reddy、M. Lakshmi Kantam

  DOI：10.1021/jo901462g

  日期：2009.10.16

  Employing CuI nanoparticles as an efficient catalyst for the cross-coupling reactions of various N/O nucleophilic reagents with aryl chlorides could be successfully carried out under mild conditions in the absence of both the ligands and strong bases. A variety of products including N-arylimidazoles and aryl ethers were synthesized in good to excellent yields.
• CuBr/<i>rac</i>-BINOL-Catalyzed <i>N</i>-Arylations of Aliphatic Amines at Room Temperature
  作者：Deshou Jiang、Hua Fu、Yuyang Jiang、Yufen Zhao

  DOI：10.1021/jo062060e

  日期：2007.1.1

  We have developed an efficient and readily available catalyst system CuBr/racemic BINOL (1,1'-binaphthyl-2,2'-diol) that catalyzes N-arylation of aliphatic amines at room temperature, and this inexpensive catalyst system is of high selectivity and tolerance toward various functional groups in the substrates.
• Markov, V. I.; Dmitrikova, L. V.; Dubina, V. L., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 11, p. 2222 - 2223
  作者：Markov, V. I.、Dmitrikova, L. V.、Dubina, V. L.、Burmistrov, K. S.

  DOI：——

  日期：——