N-(p-methoxybenzylidene)methylamine N-oxide | 16089-66-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(p-methoxybenzylidene)methylamine N-oxide
• 英文别名: N-methyl-4-methoxybenzylidene amine N-oxide；(p-C6H4OMe)C(H)N(Me)O；ON(Me)C(H)C6H4OMe-p；4-Methoxy-benzaldehyd-N-methyl-nitron；1-(4-methoxyphenyl)-N-methylmethanimine oxide
• CAS: 16089-66-0；102972-06-5；203731-09-3
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: HVBZJCSNXVMPIH-JXMROGBWSA-N

物化性质

• 沸点：
  293.1±42.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 储存条件：
  2-8℃

反应信息

• 作为反应物：
  描述：

  N-(p-methoxybenzylidene)methylamine N-oxide 在 tetrabutylammonium tetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 (1S,4S,5S)-4-(4-Methoxy-phenyl)-3-methyl-2-oxa-3-aza-bicyclo[3.2.0]heptane
  参考文献：
  名称：

  电生成的活化烯烃与硝酮的1,3-偶极环加成反应。1-芳基磺酰基环丁烯在合成新的异恶唑烷中的用途

  摘要：

  具体地，通过将​​1，3-偶极环加成到多个硝酮中，然后进行阴极裂解，可以将电生成的1-磺酰基环丁烯容易地用于2-氧杂-3-氮杂双环[3,2,0]庚烷的合成。

  DOI：

  10.1016/s0040-4039(97)10701-8
• 作为产物：
  描述：

  N-p-methoxybenzyl-N-methylhydroxylamine 在 mercury(II) oxide 作用下， 以 氘代氯仿 为溶剂， 反应 2.0h， 生成 N-(p-methoxybenzylidene)methylamine N-oxide 、 C-(4-methoxyphenyl)-N-methyl nitrone
  参考文献：
  名称：

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

  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
• α,β-Unsaturated Fischer Carbene Complexes vs. 1,3-Dipoles: Reactions with Nitrones and Nitrilimines
  作者：José Barluenga、Félix Fernández-Marí、Rosario González、Enrique Aguilar、Gustavo A. Revelli、Argimiro L. Viado、Francisco J. Fañanás、Bernardo Olano

  DOI：10.1002/(sici)1099-0690(200005)2000:9<1773::aid-ejoc1773>3.0.co;2-e

  日期：2000.5

  The reaction of tert-butylalkynyl chromium Fischer carbene complex 1 with nitrones 2 affords β-enamino-ketoaldehydes 4 by the light-promoted rearrangement of the corresponding [3+2] cycloadduct carbene complexes 3. On the other hand, [3+2] cycloaddition of chiral nonracemic Fischer alkenyl carbene complexes 19 with nitrilimines 10 yields enantiomerically pure Δ2-pyrazolines with high regio- and diastereoselectivity

  叔丁基炔基铬 Fischer 卡宾配合物 1 与硝酮 2 的反应通过相应的 [3+2] 环加合物卡宾配合物 3 的光促进重排得到 β-烯氨基-酮醛 4。另一方面，[3+2]手性非外消旋 Fischer 烯基卡宾配合物 19 与腈亚胺 10 的环加成产生具有高区域选择性和非对映选择性的对映异构纯 Δ2-吡唑啉。
• Synthesis and mass spectral study of new phenylsulfonyl substituted isoxazolidines
  作者：Yaşar Dürüst、Cevher Altuğ、Jari Sinkkonen、Olli Martiskainen、Kalevi Pihlaja

  DOI：10.1002/jhet.5570430519

  日期：2006.9

  Ten 2,3-disubstituted 4-phenylsulfonyl isoxazolidines (3a-j) were prepared by 1,3-dipolar cycloaddition reaction of substituted nitrones (1a-j) with phenyl vinyl sulfone (2). The reaction products were identified by means of IR, NMR, and MS data. In addition, the factors influencing on the electron ionization induced mass spectral fragmentation of the title products are discussed in detail.

  通过取代的硝酮（1a-j）与苯基乙烯基砜（2）的1，3-偶极环加成反应制备了十个2，3-二取代的4-苯基磺酰基异恶唑烷（3a-j）。通过IR，NMR和MS数据鉴定反应产物。此外，还详细讨论了影响电子离解引起标题产物质谱碎裂的因素。
• Ring-opening of isoxazolidine nucleus: Competitive formation of α,β-enones and tetrahydro-1,3-oxazines
  作者：Franco Casuscelli、Ugo Chiacchio、Antonio Rescifina、Roberto Romeo、Giovanni Romeo、Silvana Tommasini、Nicola Uccella

  DOI：10.1016/0040-4020(95)00030-c

  日期：1995.3

  Treatment of isoxazolidine derivatives with methyl iodide, followed by simple heating with aqueous NaOH, gives rise to a competitive formation of alpha,beta-enones and tetahydro-1,3-oxazines. The ring-opening process is controlled by the stereochemistry of H-5 which represents the driving factor of two competitive reaction routes.
• 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)].