N-(p-nitrobenzylidene)methylamine N-oxide | 16089-71-7

• 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-(p-nitrobenzylidene)methylamine N-oxide
• 英文别名: (p-C6H4NO2)C(H)N(Me)O；methyl-(4-nitro-benzylidene-(seqtrans))-amine oxide；ON(Me)C(H)C6H4NO2-p；Methyl-(4-nitro-benzyliden-(seqtrans))-aminoxyd；N-methyl-1-(4-nitrophenyl)methanimine oxide
• CAS: 16089-71-7；57414-31-0；97792-07-9
• 化学式: C₈H₈N₂O₃
• 分子量: 180.163
• InChiKey: XTGQIXWPHQOCGD-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(p-nitrobenzylidene)methylamine N-oxide 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 76.0h， 生成 N,5-(S)-dimethyl-3-(R)-(p-nitrophenyl)isoxazolidine-5-carboxylic acid
  参考文献：
  名称：

  硝基酮与 (S)-(-)-4-Benzyl-N-methacryloyl-2-oxazolidinone 的不对称 1,3-偶极环加成反应

  摘要：

  硝酮与 (S)-(-)-4-苄基-N-甲基丙烯酰基-2-恶唑烷酮的不对称 1,3-偶极环加成反应 [3+2]-硝酮介导的 (S)-(-) 环加成反应-4-benzyl-N-methacryloyl-2-oxazolidinone 已用于合成具有可控立体化学的高度取代的异恶唑烷。从对应的 X射线结构。

  DOI：

  10.1055/s-2005-869992
• 作为产物：
  描述：

  C-(4-nitrophenyl)-N-methylnitrone 生成 N-(p-nitrobenzylidene)methylamine N-oxide
  参考文献：
  名称：

  Thompson; Baer, Journal of the American Chemical Society, 1940, vol. 62, p. 2095

  摘要：

  DOI：

文献信息

• Regioselective synthesis of some isoxazolines and isoxazolidines bearing caprolactam moiety
  作者：Akın Sağirli、Yaşar Dürüst

  DOI：10.1080/00397911.2018.1448934

  日期：2018.6.18

  room temperature and the best protocol have been found for the transformation of nitrones to N-methyl isoxazolidines is silver acetate in refluxing xylene. The structural identification of target compounds was established by IR, nuclear magnetic resonance (NMR), high resolution mass spectrometry (HRMS) spectra, and X-ray diffraction analyses. GRAPHICAL ABSTRACT

  摘要异恶唑啉和异恶唑烷系列是通过芳香醛酮和腈氧化物与 N-乙烯基己内酰胺通过区域选择性 1,3-偶极环加成反应获得的，仅以中等产率产生 5-己内酰胺取代的区域异构体。使用不同条件优化环加成反应。用于将腈氧化物转化为异恶唑的一种是室温下的三乙胺，并且已发现将硝酮转化为 N-甲基异恶唑的最佳方案是回流二甲苯中的乙酸银。目标化合物的结构鉴定是通过红外、核磁共振 (NMR)、高分辨率质谱 (HRMS) 光谱和 X 射线衍射分析建立的。图形概要
• Aurich, Hans Guenter; Duggal, Suresh K.; Hoehlein, Peter, Chemische Berichte, 1981, vol. 114, # 7, p. 2440 - 2449
  作者：Aurich, Hans Guenter、Duggal, Suresh K.、Hoehlein, Peter、Klingelhoefer, Hans-Georg、Weiss, Wolfram

  DOI：——

  日期：——
• Hassan, Azfar; Wazeer, Mohammed I. M.; Ali, Sk. Asrof, Journal of the Chemical Society. Perkin Transactions 2 (2001), 1998, # 2, p. 393 - 399
  作者：Hassan, Azfar、Wazeer, Mohammed I. M.、Ali, Sk. Asrof

  DOI：——

  日期：——
• Platinum(IV)-Assisted [2 + 3] Cycloaddition of Nitrones to Coordinated Organonitriles. Synthesis of Δ⁴-1,2,4-Oxadiazolines
  作者：Gabriele Wagner、Armando J. L. Pombeiro、Vadim Yu. Kukushkin

  DOI：10.1021/ja993564f

  日期：2000.4.1

  [2 + 3] cycloaddition between acetonitrile ligands in the platinum(IV) complex [PtCl4(MeCN)(2)] and the nitrones -O+N(R-3)=C(R-1)(R-2) [R-1 = H, R-2 = Ph, sigma-C6H4OH, p-C6H4Me, p-C6H4OMe, p-C6H4NO2, p-C6H4NMe2, p-C6H4NMe2.HCl, R-3 = Me; R-1 = H, R-2 = Ph, 'Bu, R-3 = CH2Ph] proceeds smoothly under mild conditions and gives the first examples of Delta(4)-1,2,4-oxadiazoline complexes, [PtCl4(N=C(Me)O-N(R-3)-C)(R-1)(R-2)}(2)], as a 1:1 mixture of two diastereoisomers. in 70-90% yields. The heterocyclic ligands were liberated almost quantitatively by reaction at room temperature of the complexes with a slight excess of pyridine in chloroform giving free (N=C(Me)O-N(R-3)-C)(R-1)(R-2) and trans-[PtCl4(pyridine)(2)]; subsequent workup allowed the isolation of the novel Delta(4)-1,2,4-oxadiazolines. All prepared compounds were characterized by elemental analyses. FAB or EI mass spectrometry, and IR and H-1, C-13H-1}, and (195)pt (metal complexes) NMR spectroscopies: X-ray structure determination was performed for the (R,S) diastereoisomer of trans-[PtCl4(N=C(Me)ON(Me)-C)H(p-C6H4OMe)}(2)].
• 1,3-Dipolar Cycloaddition of Nitrones to a Nitrile Functionality in <i>closo</i>-Decaborate Clusters: A Novel Reactivity Mode for the Borylated C≡N Group
  作者：Aleksey L. Mindich、Nadezhda A. Bokach、Fedor M. Dolgushin、Matti Haukka、Leonid A. Lisitsyn、Andrey P. Zhdanov、Konstantin Yu. Zhizhin、Serguei A. Miltsov、Nikolay T. Kuznetsov、Vadim Yu. Kukushkin

  DOI：10.1021/om200993f

  日期：2012.3.12

  The Z-configured nitrones -O+N(Me)=C(H)C6H4R2-p (R-2 = OMe (2a), Me (2b), NO2 (2c)) react with the nitrile functionality of the closo-decaborate clusters [(Bu4N)-N-n][B10H9(NCR1)] (RI = Me (la), Et (1b), Bu-t (1c), Ph (1d)) in CHCl3 solution under mild conditions (20-25 degrees C, 16-18 h) to afford the products of cycloaddition: viz., the borylated 2,3-dihydro-1,2,4-oxadiazoles [(Bu4N)-N-n][B10H9N-a = (CRON)-O-1 (Me)(CH)-H-b(C6H4R2-p)}]((a -b)) (3a-1). This reaction represents the first example of boron-mediated 1,3-dipolar cycloaddition of allyl anion type dipoles, i.e. nitrones, to the nitrile group. Alteration of the lipophilic [(Bu4N)-N-n]. counterion with the hydrophilic Na+ via the metathetical reaction with NaBPh4 in 3a,b,e,f allows the modification of their hydrophilic-lipophilic properties and, consequently, solubility. Compounds 3a-j and 5a-d were characterized by high-resolution ESI-MS, IR, and H-1, C-13H-1}, and B-11H-1} NMR spectroscopy. The structures of 3a,e,f were determined by single-crystal X-ray diffraction.