glyoxime-N.N'-diphenyl ether | 13532-81-5

• 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: glyoxime-N.N'-diphenyl ether
• 英文别名: N,N'-1,2-Ethanediylidenebis(benzeneamine) N,N'-Dioxide；Ethandiyliden-bis-(anilin-N-oxid)；N.N'-Diphenyl-glyoxaldiisoxim；Glyoxim-N.N'-diphenylaether；Glyoxal-bis-(N-phenyl-oxim)；Glyoxal-bis-；2-(N-oxidoanilino)ethenyl-oxo-phenylazanium
• CAS: 13532-81-5
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: GVCSWQQZBJTDLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  glyoxime-N.N'-diphenyl ether 在 乙酸酐 、 溶剂黄146 作用下， 生成 草酰苯胺
  参考文献：
  名称：

  v. Pechmann, Chemische Berichte, 1897, vol. 30, p. 2463,2878

  摘要：

  DOI：
• 作为产物：
  描述：

  苯基羟胺 在 乙醇 、 水 、 碳酸氢钠 作用下， 生成 glyoxime-N.N'-diphenyl ether
  参考文献：
  名称：

  Bamberger; Landau, Chemische Berichte, 1919, vol. 52, p. 1102

  摘要：

  DOI：

文献信息

• Rhodium nitrone complexes: efficient catalyst for carbonylation of methanol
  作者：Pankaj Das、Monalisa Boruah、Nandini Kumari、Manab Sharma、Dilip Konwar、Dipak K Dutta

  DOI：10.1016/s1381-1169(01)00338-7

  日期：2002.1

  Newly synthesized rhodium(I) carbonyl complexes of the type [Rh(CO)2ClL] (1), where L=α,N-diphenylnitrone (a), α-styryl-N-phenylnitrone (b), N,N′-diphenyldinitrone (c) and α-(2-furyl)-N-phenylnitrone (d), act as efficient catalyst precursors (maximum turn over number (TON) 1200–1400 per 90 min) for carbonylation of methanol to produce acetic acid and its ester at temperature 150±10 °C and pressure

  新合成的铑（I）的类型的[Rh（CO）的羰基配合物2 CLL]（1），其中L =α，Ñ -diphenylnitrone（一），α-苯乙烯基Ñ -phenylnitrone（b），Ñ，Ñ ' -二苯二酮（c）和α-（2-呋喃基）-N-苯基硝基（d）可作为有效的催化剂前体（每90分钟的最大转换数（TON）1200-1400）用于甲醇羰基化生产乙酸和其酯在温度150±10°C和压力20 bar下使用。
• Synthesis of Some Novel Bisisoxazolidine Derivatives from Glyoxal-derived Bisnitrones via Simultaneous Double Cycloaddition Reactions in Water
  作者：Bhaskar Chakraborty、Govinda Prasad Luitel

  DOI：10.1002/jhet.2181

  日期：2015.5

  Simultaneous double 1,3‐dipolar cycloaddition reactions of glyoxal‐derived bisnitrones have been described in water. Significant rate acceleration and improved yields of exclusively diastereoselective and regioselective bisisoxazolidines in water have been observed at room temperature in a short reaction time compared with conventional solvents.

  乙二醛衍生的双硝基酮在水中同时发生双1,3-偶极环加成反应。与常规溶剂相比，在室温下，在较短的反应时间内即可观察到在水中的非对映选择性和区域选择性联苯二恶唑烷类化合物的明显速率加速和提高的收率。
• Semi-synthesis of a novel hybrid isoxazolidino withaferin via chemoselective and diastereoselective 1,3-dipolar nitrone cycloaddition reaction
  作者：Ramkrishna Mandal、Meenakshi Singh、Amrutha A.V. Krishnan、Yogita H. Dahat、Yogesh P. Bharitkar、V. Ravichandiran、Abhijit Hazra

  DOI：10.1080/14786419.2019.1582045

  日期：2020.8.2

  A facile, atom-economic synthesis of isoxazilidino withaferin, a novel hybrid of withaferin A, has been accomplished via two-step reaction of nitrone synthesis followed by nitrone 1,3-dipolar cycloaddition. The reaction is highly chemoselective (preferential reaction only on one of the two double bonds present on withaferin A) and diastereoselective affording exclusively the cis-fused products. The

  一种新的withaferin A杂种的异恶嗪利迪酮withaferin的原子经济经济合成方法是通过硝酮合成的两步反应，然后进行硝酮1,3-偶极环加成反应完成的。该反应是高度化学选择性的（仅对存在于枯草杆菌素A上的两个双键中的一个优先反应），并且是非对映选择性的，仅提供顺式融合产物。通过详细分析1D，2D NMR和质谱数据确定结构。
• Nitroxides as reaction intermediates
  作者：Hans Gunter Aurich

  DOI：10.1139/v82-206

  日期：1982.6.15

  Vinyl nitroxides 4 are obtained by oxidation of the nitrones 3, as was shown by esr studies and by identification of the reaction products. The formation of 4d–f is even observed in oxidation of the hydroxylamines 1d–f, nitroxides 2d–f and nitrones 3d–f being the intermediates. The high reactivity of the vinyl nitroxides 4 at their β-position is illustrated by the reactions of 4a with various compounds affording the nitroxides 7–10, respectively. Compound 4c reacts with its precursor 3c to give 11, 12, or 13, depending on the reaction conditions. From oxidation of 3a, c, and e the dimerization products 5a, c, and e, respectively, could be isolated. Whereas further oxidation of 5d yields 6d, the acyl nitroxides 14a and c are formed in the oxidation of 5a and c, respectively.The formation of quinone 23 in the reaction of 2-methyl-2-nitrosopropane with potassium tert-butoxide in isopropyl alcohol in the presence of oxygen is discussed. The nitroxide 20 has been detected in the reaction mixture. Imines 24 react with nitrosobenzene giving nitroxides 26. These are further oxidized by nitrosobenzene to afford nitrones 27. Whereas 27a and b could be isolated, 27c and d undergo further reaction yielding the diimines 30c and d along with dinitrone 29.The formation and reactions of imino nitroxides 31 and of the nitronyl nitroxide 41 are discussed. Electron spin resonance studies revealed the high reactivity of the imidazolyl-1,3-dioxides 46 and the imidazolyl-1-oxides 50, which easily form radicals 47–49 and 51, respectively, which are derived from secondary reactions.

  乙烯基亚硝基化合物4是通过氧化亚硝基化合物3获得的，这已经通过esr研究和反应产物的鉴定得到证明。4d-f的形成甚至在羟胺1d-f、亚硝基化合物2d-f和亚硝基化合物3d-f的氧化中也被观察到，其中亚硝基化合物3d-f是中间体。乙烯基亚硝基化合物4在其β位的高反应性可通过4a与各种化合物的反应得到证明，分别得到亚硝基化合物7-10。化合物4c与其前体3c反应，根据反应条件可得到11、12或13。从3a、c和e的氧化中可以分离出二聚体化合物5a、c和e。而5d的进一步氧化则产生6d，在5a和c的氧化中形成酰基亚硝基化合物14a和c。讨论了2-甲基-2-亚硝基丙烷与叔丁氧基钾在异丙醇中存在氧气时生成喹啉23的反应。在反应混合物中检测到亚硝基化合物20。亚胺24与亚硝基苯反应生成亚硝基化合物26。这些化合物进一步被亚硝基苯氧化生成亚硝基化合物27。虽然27a和b可以被分离，但27c和d会进一步反应，产生二亚胺30c和d以及二亚硝基化合物29。讨论了亚胺亚硝基化合物31和亚硝基亚硝基化合物41的形成和反应。电子自旋共振研究揭示了咪唑基-1,3-二氧化物46和咪唑基-1-氧化物50的高反应性，它们很容易形成由二次反应得到的自由基47-49和51。
• v.Pechmann; Ansel, Chemische Berichte, 1900, vol. 33, p. 1299
  作者：v.Pechmann、Ansel

  DOI：——

  日期：——