1-(4-methoxy-phenyl)-2-nitro-ethanone oxime | 70976-24-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-methoxy-phenyl)-2-nitro-ethanone oxime
• 英文别名: (NZ)-N-[1-(4-methoxyphenyl)-2-nitroethylidene]hydroxylamine
• CAS: 70976-24-8
• 化学式: C₉H₁₀N₂O₄
• 分子量: 210.189
• InChiKey: MSDZWBWQBKUNBN-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  87.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲氧基苯乙烯 在 亚硝酸特丁酯 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以63%的产率得到1-(4-methoxy-phenyl)-2-nitro-ethanone oxime
  参考文献：
  名称：

  叔丁基亚硝酸盐硝化-氧化苯乙烯衍生物：α-硝基肟的合成

  摘要：

  开发了一种高效的方法，用于在DMSO中使用亚硝酸叔丁酯（t -BuONO）对苯乙烯衍生物进行直接硝化-肟化。本方法为中等至高产率的α-硝基肟的合成提供了方便实用的方法。其显着特征包括温和的反应条件，无金属的试剂，对环境无害的溶剂以及简单的实验程序。

  DOI：

  10.1002/cjoc.201600167

文献信息

• Convenient synthesis of α-nitrooximes mediated by OXONE^®
  作者：Napasawan Chumnanvej、Natthapol Samakkanad、Manat Pohmakotr、Vichai Reutrakul、Thaworn Jaipetch、Darunee Soorukram、Chutima Kuhakarn

  DOI：10.1039/c4ra11703d

  日期：——

  A novel OXONE® mediated direct difunctionalization of alkenes with NaNO2 in aqueous acetonitrile for the synthesis of α-nitrooximes was developed. The α-nitrooximes were readily prepared in moderate to high yields at room temperature under mild reaction conditions. The present protocol offers an easy and environmentally benign approach to access various α-nitrooximes derived from styrene derivatives.

  开发了一种新型的OXONE®介导的烯烃直接双官能团化反应，使用水合乙腈中的NaNO2合成α-硝基肟。在温和的反应条件下，室温下即可方便地以中等到高产率制备α-硝基肟。该方案提供了一种简单且环境友好的方法，用于从苯乙烯衍生物获取多种α-硝基肟。
• Synthesis and tautomerization study of pseudonitrosites to 1,2-nitroximes
  作者：Ahmad Shaabani、Hamid Reza Bijanzadeh、Ali Reza Karimi、Mohammad Bagher Teimouri、Kamal Soleimani

  DOI：10.1139/v08-011

  日期：2008.3.1

  4-R-Substituted 2-nitro-1-nitrosoethylbenzenes (R = H, CH₃, OCH₃, Cl, F) have been synthesized under solvent-free conditions and the mechanism of their tautomerization to 2-isonitroso-1-nitro-2-phenylethanes have been investigated by ¹H NMR spectroscopy.Key words: tautomerization, pseudonitrosite, mechanism, 2-nitro-1-nitrosoethylbenzene, ¹H NMR spectroscopy

  在无溶剂条件下合成了4-R-取代的2-硝基-1-亚硝基乙苯（R = H, CH3, O , Cl, F），并通过1H NMR光谱研究了它们同素异构为2-异硝基-1-亚硝基-2-苯乙烷的机理。
• Water-controlled nitro-oximation of alkenes under catalyst-free conditions
  作者：Lin Tang、Zhen Yang、Xueping Chang、Guodong Zou、Yuqiang Zhou、Weihao Rao、Xiantao Ma、Geng Zhao

  DOI：10.1016/j.tetlet.2018.10.037

  日期：2018.11

  A convenient and precise nitration and oximation of alkenes with tert-butyl nitrite has been reported, yielding alpha-nitro ketoximes in satisfactory yields with broad substrate generality and excellent stereoselectivity under mild conditions. Experiments indicate that tert-butyl nitrite serves as both NO and NO2 sources and water plays a key role in this difunctionalization reaction. (C) 2018 Elsevier Ltd. All rights reserved.
• Synthesis of <font>α</font>-Nitro Ketoximes from Styrenes and <i>tert</i>-Butyl Nitrite
  作者：Qi Cao、Jidan Liu、Lin Yu、Qingwen Gui、Xiang Chen、Ze Tan

  DOI：10.1080/00397911.2015.1062988

  日期：2015.10.2

  We have discovered that various -nitro ketoximes can be synthesized in good yields starting from styrenes and tert-butyl nitrite. The success of the reaction was critically dependent on the use of a mixture solvent of dimethylsulfoxide and water. The reaction can tolerate a wide variety of substituents including electron-withdrawing and electron-donating groups.
• Pseudonitrosites and Other Azodioxides with Vicinal Electron Acceptors
  作者：Klaus Rehse、Martin Herpel

  DOI：10.1002/(sici)1521-4184(199803)331:3<111::aid-ardp111>3.0.co;2-z

  日期：1998.3

  Twelve vicinally substituted nitro-nitroso compounds (pseudonitrosites) were synthesized, nine of them for the first time. In the solid state the dimeric azodioxides are present. In the class of the pseudonitrosites 2a-h, all compounds exhibited comparatively strong antiplatelet activity in vitro (Born test: collagen). Four of them showed an IC50 below 10 mu M, 2a being the most active I substance with an IC50 = 2.1 mu M. When administered orally to rats (60 mg/kg) small antithrombotic effects were observed. The pseudonitrosite 6d was the most active compound(18% inhibition in arterioles). The in vitro decomposition of 2a at 37 degrees C gave NO and N2O, indicating that the above pharmacological effects were mediated by an NO-dependent mechanism. The replacement of the nitro group in the pseudonitrosite partial structure by other electron accepters i.e. acetyl, carboxyl, or acetyloxy groups leads to inactive (10a) or less active compounds (10b, c).