4-(4-硝基苯氧基)丁烷-2-酮 | 57027-70-0

• 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: 4-(4-硝基苯氧基)丁烷-2-酮
• 英文名称: 4-(4-nitrophenoxy)-2-butanone
• 英文别名: 4-(4-nitrophenoxy)butan-2-one；4-(4-nitrophenyl)-2-butanone；4-(4-Nitrophenoxy)-2-butanon；4-p-Nitrophenoxy-2-butanon
• CAS: 57027-70-0
• 化学式: C₁₀H₁₁NO₄
• mdl: MFCD12818653
• 分子量: 209.202
• InChiKey: VWPARFIUQVKLJS-UHFFFAOYSA-N

物化性质

• 沸点：
  367.8±22.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-硝基苯氧基)丁烷-2-酮 以 四氢呋喃 、 氯苯 为溶剂， 生成 4-硝基苯酚阴离子 、 丁烯酮
  参考文献：
  名称：

  Proximity as a component of organic reactivity

  摘要：

  DOI：

  10.1021/ja00302a017
• 作为产物：
  描述：

  对硝基苯酚 、 丁烯酮 在 1-甲基-3-丁基咪唑硫酸氢盐 作用下， 反应 24.0h， 以30%的产率得到4-(4-硝基苯氧基)丁烷-2-酮
  参考文献：
  名称：

  Highly Chemo- and Regioselective Reaction of Hydroxybenzenes in Acidic Ionic Liquid

  摘要：

  首次报道了羟基苯与酸性离子液体l-丁基-3-甲基咪唑盐酸([BMIM]HSO4)中α,β-不饱和化合物的高度化学和区域选择性反应。合成了一系列oxa-Michael加成物和Friedel-Crafts烷基化产物，产率良好。酸性离子液体可轻松回收至少5次，活性仅有微小损失。

  DOI：

  10.5012/bkcs.2013.34.9.2594

文献信息

• Solvation changes accompanying proton transfer from a carbon acid to alkoxide bases as revealed by kinetic isotope effects
  作者：Thomas E. Casamassina、W. Phillip Huskey

  DOI：10.1021/ja00054a003

  日期：1993.1

  Primary hydrogen isotope effects are reported for the elimination of 4-nitrophenol from 4-(4-nitrophenoxy)-2-butanone in methanolic methoxide at 20 o C and in aqueous hydroxide at 25 o C. The isotope effects do not change significantly when the isotopic composition of the solvents is changed: (κ H /κ D ) MeOD =6.48±0.22, (κ H /κ D ) MeOD =6.40±0.24; and (κ H /κ D ) HOH =7,5±0.11, (κ H /κ D ) DOD =7

  据报道，从 4-(4-硝基苯氧基)-2-丁酮中的 4-(4-硝基苯氧基)-2-丁酮在 20 o C 的甲醇甲醇和 25 o C 的氢氧化物水溶液中消除 4-硝基苯酚的主要氢同位素效应。当溶剂同位素组成发生变化：(κ H /κ D ) MeOD =6.48±0.22，(κ H /κ D ) MeOD =6.40±0.24；(κ H /κ D ) HOH =7,5±0.11, (κ H /κ D ) DOD =7,48±0.21。动力学溶剂同位素效应（使用未氘化底物）是 κ MeOD /κ MeOH =2.195±0.064 和 κ DOD /κ HOH =1.526±0.029
• Acidic ionic liquid [NMP]H2PO4 as dual solvent-catalyst for synthesis of β-alkoxyketones by the oxa-Michael addition reactions
  作者：Hui Guo、Xia Li、Jun-Liang Wang、Xiao-Han Jin、Xian-Fu Lin

  DOI：10.1016/j.tet.2010.08.017

  日期：2010.10

  Acidic ionic liquid N-methyl-2-pyrrolidonium dihydrogen phosphate [NMP]H2PO4 was prepared and used as efficient catalyst and reaction medium to synthesize beta-alkoxyketones by the oxa-Michael addition reactions for the first time. The effect of anions and cations, amount of ionic liquid on the reaction was investigated. Various alcohols and phenols proceeded smoothly and led to corresponding beta-alkoxyketones with high yields under mild reaction conditions, O-selectivity addition of amino-ethanols was also achieved in this paper. Compared with traditional imidazolium ionic liquids, [NMP] H2PO4 gave the better results. The ionic liquid was stable and could be reused at least five times with a slight loss of activity. (C) 2010 Published by Elsevier Ltd.
• Highly Chemo- and Regioselective Reaction of Hydroxybenzenes in Acidic Ionic Liquid
  作者：Hui Guo、Yu Wei Zhuang、Jian Cao、Guo Bao Zhang

  DOI：10.5012/bkcs.2013.34.9.2594

  日期：2013.9.20

  Highly chemo- and regioselective reaction of hydroxybenzenes with $\alpha},\beta}$-unsaturated compounds in acidic ionic liquid l-butyl-3-methylimidazolium hydrogen sulphate ([BMIM]HSO4) was reported for the first time. A series of oxa-Michael adducts and Friedel-Crafts alkylated products were synthesized with good yields. The acidic ionic liquid could be easily recycled for at least 5 times with only minor loss in activity.

  首次报道了羟基苯与酸性离子液体l-丁基-3-甲基咪唑盐酸([BMIM]HSO4)中α,β-不饱和化合物的高度化学和区域选择性反应。合成了一系列oxa-Michael加成物和Friedel-Crafts烷基化产物，产率良好。酸性离子液体可轻松回收至少5次，活性仅有微小损失。
• Proximity as a component of organic reactivity
  作者：F. M. Menger、U. V. Venkataram

  DOI：10.1021/ja00302a017

  日期：1985.8