C-(4-nitrophenyl)-N-methylnitrone | 97792-07-9

• 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: C-(4-nitrophenyl)-N-methylnitrone
• 英文别名: N-methyl-1-(4-nitrophenyl)methanimine oxide
• CAS: 97792-07-9
• 化学式: C₈H₈N₂O₃
• 分子量: 180.163
• InChiKey: XTGQIXWPHQOCGD-TWGQIWQCSA-N

物化性质

• 沸点：
  348.5±44.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

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：

  C-(4-nitrophenyl)-N-methylnitrone 在 碘甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (E)-ethyl 2-benzoyl-3-(4'-nitrophenyl)-2-propenoate
  参考文献：
  名称：

  Ring-Opening of 4-Isoxazolines: Competitive Formation of Enamino Derivatives and a,b-Enones

  摘要：

  Ring-opening of 3-substituted 4-isoxazolines, proceeding through the intermediate isoxazolinium salts, follows two competing reaction pathways leading to alpha,beta-enones and enamines respectively. The rearrangement courses can be controlled as a function of substitution pattern and experimental conditions.

  DOI：

  10.3987/com-92-6223
• 作为产物：
  描述：

  (3S)-cis-2-methyl-3-(4-nitro-phenyl)-oxaziridine 以 氘代氯仿 为溶剂， 反应 17.0h， 以22%的产率得到C-(4-nitrophenyl)-N-methylnitrone
  参考文献：
  名称：

  Boyd, Derek R.; Campbell, Rose M.; Coulter, Peter B., Journal of the Chemical Society. Perkin transactions I, 1985, p. 849 - 856

  摘要：

  DOI：

文献信息

• Solvent-free synthesis of nitrones in a ball-mill
  作者：Evelina Colacino、Pierrick Nun、Francesco Maria Colacino、Jean Martinez、Frédéric Lamaty

  DOI：10.1016/j.tet.2008.03.091

  日期：2008.6

  13C MAS nuclear magnetic resonance experiments. We have also studied the temperature profile during the reaction. A comparative study with the corresponding solvent-free microwave activated reaction showed the superiority of the ball-milling method; 31 examples are described, including the synthesis of the anti-aging agent C-phenyl-N-tert-butyl nitrone (PBN) and one of its analogues C-2-pyridyl-N-tert-butylnitrone

  在无溶剂条件下，在球磨机中，通过等摩尔量的醛和N-取代的羟胺缩合，在0.5–2小时内合成了各种C-芳基和C-烷基-硝基。无需排除空气和水分即可进行反应，无需进一步纯化即可得到预期的产物。差示扫描量热法（DSC）和固态13对该研究进行了补充C MAS核磁共振实验。我们还研究了反应过程中的温度曲线。与相应的无溶剂微波活化反应的比较研究表明，球磨法具有优越性。31个实施例中描述，包括抗老化剂的合成Ç苯基ñ -叔丁基硝酮（PBN）和其类似物的一个Ç -2-吡啶基- ñ -叔-butylnitrone（2- PyBN）。
• Electronic effects in 1,3-dipolar cycloaddition reactions of N-alkyl and N-benzyl nitrones with dipolarophiles
  作者：Andrei Bădoiu、E. Peter Kündig

  DOI：10.1039/c1ob06144e

  日期：——

  1,3-Dipolar cycloadditions afforded fast access to isoxazolidines bearing N-alkyl or N-benzyl substituents. The electronic properties of the substituents in the nitrones define the activity of the dipoles and modulate diastereoselectivity in the non-catalyzed reactions. Using a chiral one-point binding ruthenium Lewis acid catalyst, products were obtained in good yields and with excellent regio-, diastereo-

  1，3-偶极环加成可快速接近带有N-烷基或N-苄基取代基的异恶唑烷。硝酮中取代基的电子性质定义了偶极子的活性，并调节了非催化反应中的非对映选择性。使用手性单点结合钌路易斯酸催化剂，可以以良好的收率和优异的区域，非对映和对映选择性获得产物。
• [3+2] Cycloadditions: Part XXXIV: Further Investigations of Cycloadditions of C,N-Diaryl- and C-Aryl-N-methyl Nitrones to α,β-Unsaturated Esters
  作者：Sumana Sengupta、Avijit Banerji

  DOI：10.14233/ajchem.2019.22232

  日期：2019.11.30

  as three atom components (TAC) to substituted methyl E-cinnamates and diethyl arylidene malonates have been further investigated. [3+2] Cycloadditions of cinnamates yielded mixtures of cycloadducts, the major products being the 3,4-trans-4,5-trans-2,3,5-triaryl-4-carbomethoxy products originating from the endo-carbonyl-exo-aryl meta channel approach of the cinnamate component. [3+2] Cycloadditions to

  进一步研究了 C,N-二芳基和 C-芳基-N-甲基硝酮作为三原子组分 (TAC) 与取代的 E-肉桂酸甲酯和亚芳基丙二酸二乙酯的 [3+2] 环加成反应。肉桂酸酯的[3+2]环加成反应产生环加合物的混合物，主要产物是源自内-羰基-外的3,4-反式-4,5-反式-2,3,5-三芳基-4-甲甲氧基产物肉桂酸酯成分的芳基元通道方法。[3+2]与亚芳基丙二酸二乙酯的环加成通过2π-组分的内芳基间通道方法提供单一环加合物-3,5-反式-2-甲基-3,5-二芳基-4,4-二乙氧基异恶唑烷。
• Reactions of nitrones with sodium iodide-trifluoroacetic anhydride system. Comments on the Beckmann rearrangement of aldonitrones and competitive processes of nucleophilic addition
  作者：Józef Drabowicz、Andrzej Kotyński、Zbigniew H. Kudzin、Ryszard B. Nazarski、Maciej K. Tasz

  DOI：10.1016/s0040-4020(97)00918-6

  日期：1997.10

  The systematic studies of the reaction of aldonitrones with the NaI-TFAA system were performed. The reaction engaged was recognised as a previously known process called ‘the Beckmann rearrangement of nitrones’. Some mechanistic considerations on this transformation and competitive nucleophilic additions are presented in order to explain the origin of iodine release and its observed stoichiometry as well

  系统地研究了醛酮与NaI-TFAA体系的反应。进行的反应被认为是一种称为“硝酮的贝克曼重排”的先前已知方法。为了解释碘释放的起源，观察到的化学计量以及某些产物的分离，提出了有关这种转化和竞争性亲核加成的一些机械方面的考虑。假定在碘化物阴离子存在下C-和N-碘物种（包括碘鎓阳离子）的中间性。
• A Novel Nitrone Cycloaddition/Rearrangement
  作者：Bruce H. Toder、George B. Mullen、Vassil St. Georgiev

  DOI：10.1002/hlca.19900730119

  日期：1990.1.31

  Adamantanone-derived nitrone 4 and some other keto-nitrones, when reacted with aromatic and aliphatic aldehydes in refluxing toluene or tetrahydrofuran, formed the corresponding aldonitrones (Z)-10, the latter arising from the fragmentation of an initially formed 1,4,2-dioxazolidine 6 to adamantan-2-one and an oxaziridine intermediate 11, which then rearranges to (Z)-10.

  金刚烷酮衍生的硝酮4和其他一些酮-硝酮，当与芳族和脂族醛在回流的甲苯或四氢呋喃中反应，形成相应的aldonitrones（ż） - 10，后者从初始形成的碎片而产生1，4，2 -二恶唑烷6至金刚烷-2-酮和恶唑烷中间体11，然后将其重排为（Z）-10。