dibutyl(2,4-dinitrophenyl)amine | 75113-69-8

• 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: dibutyl(2,4-dinitrophenyl)amine
• 英文别名: N,N-di-n-butyl-2,4-dinitroaniline；N,N-dibutyl-2,4-dinitroaniline；2,4-Dinitrophenyl-di-n-butylamin；N,N-Dibutyl-2,4-dinitro-anilin；N,N-Dibutyl-2,4-dinitrobenzenamine
• CAS: 75113-69-8
• 化学式: C₁₄H₂₁N₃O₄
• 分子量: 295.338
• InChiKey: CYRRWDPFDBUXIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  94.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  三正丁胺 、 2,4-二硝基氟苯 在 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 40.0h， 以68%的产率得到dibutyl(2,4-dinitrophenyl)amine
  参考文献：
  名称：

  光氧化还原催化叔胺脱烷基芳香族卤素取代

  摘要：

  描述了带有吸电子基团的芳香族卤化物与叔胺在铱催化剂存在下在蓝光照射下的反应。获得卤化物被二烷基氨基片段芳族取代的产物。芳基自由基与叔胺相互作用产生两性离子自由基物种被认为是影响反应效率的关键因素。

  DOI：

  10.3390/molecules26113323

文献信息

• The Anomalous Reactions of Some Fluoronitrobenzenes With Some N,N-Dialkylamines
  作者：DJ Gale、J Rosevear、JFK Wilshire

  DOI：10.1071/ch9950997

  日期：——

  The reactions of 1-fluoro-2,4- and -2,6-dinitrobenzene with certain N,N- dialkylamines in dimethyl sulfoxide solution in the presence of potassium carbonate give the corresponding dinitrophenyl N,N- dialkylcarbamates as well as the corresponding N,N- dialkyldinitroanilines. The extent of carbamate formation is governed by steric factors. The corresponding reactions of 1-fluoro-4-nitrobenzene with diisopropylamine and di-s-butylamine give poor yields of the corresponding 4-nitrophenyl N,N- dialkylcarbamates but none of the corresponding N,N-dialkyl-4-nitroanilines; in these reactions, the major product is 4,4'-dinitrodiphenyl ether. The 1H and 13C n.m.r. spectra of the 2,4- and 2,6-dinitrophenyl N,N- dialkylcarbamates reveal that their aliphatic protons and carbon atoms are magnetically non-equivalent.

  在二甲基亚砜溶液中，1-氟-2,4-和-2,6-二硝基苯与某些 N,N-二烷基胺在碳酸钾存在下发生反应，生成相应的 N,N-二烷基氨基甲酸二硝基苯基酯以及相应的 N,N-二烷基二硝基苯胺。氨基甲酸酯的形成程度受立体因素的影响。在 1-氟-4-硝基苯与二异丙基胺和二叔丁基胺的相应反应中，相应的 4-硝基苯基 N,N-二烷基氨基甲酸酯的产量很低，但却没有相应的 N,N-二烷基-4-硝基苯胺；在这些反应中，主要产物是 4,4'-二硝基二苯醚。2,4- 和 2,6- 二硝基苯 N,N-二烷基氨基甲酸酯的 1H 和 13C n.m.r. 光谱显示，它们的脂肪族质子和碳原子在磁性上是不等价的。
• Azo dyes containing 1,3,4-thiadiazole fragment: synthesis and properties
  作者：Galina Selivanova、Alexandrina Skolyapova、Jiaying Wang、Elena Karpova、Inna Shundrina、Irina Bagryanskaya、Evgeny Amosov

  DOI：10.1039/d1nj05084b

  日期：——

  New 1,3,4-thiadiazole derivatives containing a diazenyl group, as well as both a diazenyl and an imino group, were synthesized and their optical and thermal properties were investigated. Initially, new azo compounds containing an azo group directly in the thiadiazole block were obtained by the coupling of diazonium bisulfates based on the previously known 5-derivatives of 2-amino-1,3,4-thiadiazoles

  合成了新的 1,3,4-噻二唑衍生物，包含一个二氮烯基，以及一个二氮烯基和一个亚氨基，并研究了它们的光学和热性能。最初，通过将基于先前已知的 2-氨基-1,3,4-噻二唑的 5-衍生物的重氮硫酸氢盐与N , N-二烷基苯胺偶联，获得了在噻二唑嵌段中直接含有偶氮基团的新偶氮化合物（ N( n- Bu) 2、NEt 2和NEt(EtOH))。通过对甲苯胺、对苯二胺和对苯二胺的相互作用获得席夫碱-氨基苯酚与在 1,3,4-噻二唑环中含有醛基的偶氮化合物。通过光谱（IR、UV、1 H NMR、13 C NMR 和质谱）和 X 射线分析对新染料进行了表征。
• A Probable Hydrogen-Bonded Meisenheimer Complex: An Unusually High S_NAr Reactivity of Nitroaniline Derivatives with Hydroxide Ion in Aqueous Media
  作者：Mitsutaka Imoto、Yasunori Matsui、Motonori Takeda、Akihiro Tamaki、Hisaji Taniguchi、Kazuhiko Mizuno、Hiroshi Ikeda

  DOI：10.1021/jo2007219

  日期：2011.8.5

  Observations show that nitroanilines exhibit an unusually high SNAr reactivity with OH- in aqueous media in reactions that produce nitrophenols. SNAr reaction of 4-nitroaniline (2a) in aqueous NaOH for 16 h yields 4-nitrophenol (4a) quantitatively, whereas a similar reaction of 4-nitrochlorobenzene (1a) gave 4a in 2% yield together with recovered la in 97%, suggesting that the leaving ability of the NH2 group far surpasses that of Cl under these conditions. An essential feature of SNAr reactions of nitroanilines is probably that the NH2 leaving group participates in a hydrogen-bonding interaction with H2O. Density functional theory (DFT) calculations for a set of 4-nitroaniline, OH-, and H2O suggest a possible formation of a Meisenheimer complex stabilized by hydrogen-bonding interactions and a six-membered ring structure. The results obtained here contrast with conventional SNAr reactivity profiles in which nitroanilines are nearly unreactive with nucleophiles in organic solvents.
• Glazer et al., Journal of the Chemical Society, 1950, p. 2657,2674
  作者：Glazer et al.

  DOI：——

  日期：——
• Ivanova, T.M.; Shein, S.M., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 891 - 897
  作者：Ivanova, T.M.、Shein, S.M.

  DOI：——

  日期：——