N-(4-dimethylaminobenzylidene)aniline oxide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(4-dimethylaminobenzylidene)aniline oxide
• 英文别名: (Z)-N-(p-dimethylamino-benzylidene)phenylamine N-oxide；N-phenyl-α-(4-dimethylamino)-nitrone；C-(4-(dimethylamino)phenyl)-N-phenylnitrone；C-(4-(N,N-dimethylamino)phenyl)-N-phenyl nitrone；α-<4-Dimethylamino-phenyl>-N-phenyl-nitron；N,N-dimethyl-4-[(oxy-phenyl-imino)-methyl]-aniline；N-(4-dimethylamino-benzylidene)-aniline N-oxide；4-dimethylamino-benzaldehyde-(N-phenyl oxime )；p-Dimethylamino-benzyliden-anilin-N-oxyd；(p-Dimethylaminophenyl)-N-phenylnitron；4-Dimethylamino-benzaldehyd-(N-phenyl-oxim)；1-[4-(dimethylamino)phenyl]-N-phenylmethanimine oxide
• 化学式: C₁₅H₁₆N₂O
• 分子量: 240.305
• InChiKey: FQARPGLFCZUGQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  32
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  六氟-2-丁炔 、 N-(4-dimethylaminobenzylidene)aniline oxide 以 四氯化碳 为溶剂， 生成
  参考文献：
  名称：

  Kobayashi,Y. et al., Heterocycles, 1977, vol. 8, p. 387 - 390

  摘要：

  DOI：
• 作为产物：
  描述：

  苯胺 、 对二甲氨基苯甲醛 在 Oxone 作用下， 以 乙腈 为溶剂， 反应 6.5h， 以81%的产率得到N-(4-dimethylaminobenzylidene)aniline oxide
  参考文献：
  名称：

  Direct oxidative synthesis of nitrones from aldehydes and primary anilines using graphite oxide and Oxone

  摘要：

  One-pot condensation/oxidation of aldehydes and primary anilines into nitrones using graphite oxide (GO) and Oxone as the oxidant under very mild reaction conditions is described. The proposed method provides a direct oxidative synthesis of various nitrones in good to excellent yields under metal-free conditions in short reaction times. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.08.049

文献信息

• Influence of the side-group at C=N bridging bond of bis-aryl Schiff bases on the wavelength of absorption maximum of ultraviolet absorption spectra
  作者：Qingqing Luo、Chao-Tun Cao、Zhongzhong Cao、Chenzhong Cao

  DOI：10.1002/poc.3550

  日期：2016.8

  methyl CH3 at carbon end and the CH=N(O) has a side‐group O atom at nitrogen end. In this work, a series of XPEAY and XPNY were synthesized, and their longest wavelength maximum λmax (nm) of ultraviolet absorption spectra were measured. Then the change regularity of the νmax (cm‐1, νmax=1/λmax) of XPEAY and XPNY were investigated, and they were compared with that of XBAY (reported by ref.26). The results

  化合物N-（亚苄基）苯胺XArCH = NArY（XBAY），N-（苯基-亚乙基）苯胺XArC（CH 3）= NArY（XPEAY）和N-苯基-α-苯基硝酮XArCH = N（O）ArY （XPNY）具有桥接基团CH = N，C（CH 3）= N和CH = N（O），其中C（CH 3）= N在碳端具有侧基甲基CH 3 = N（O）在氮端带有一个侧基O原子。在这项工作中，合成了一系列XPEAY和XPNY，并测量了它们的紫外线吸收光谱的最长波长最大值λmax（nm）。然后，ν的变化规律最大值（厘米-1，ν最大= 1 /λ最大对XPEAY和XPNY进行了调查），并与XBAY进行了比较（参考文献26报告）。结果表明：（1）XBAY与XPEAY或XPNY之间的νmax之间没有良好的线性关系。（2）在相同的一组的X-Y基团的耦合情况下，λ的分布最大XPEAYs的比XPNYs大。（3）侧基CH 3使得效
• Synthesis of novel spiro-isoxazoline and spiro-isoxazolidine derivatives of tomentosin
  作者：Mohamed Zaki、Abdelouahd Oukhrib、Mohamed Akssira、Sabine Berteina-Raboin

  DOI：10.1039/c6ra25869g

  日期：——

  A series of novel enantiomerically pure spiro-isoxazolidines and spiro-isoxazolines were synthesized regioselectively by 1,3-dipolar cycloaddition using respectively two dipoles, nitrones and nitrile oxides, on the exocyclic double bond of the B ring of tomentosin (α-methylene-γ-butyrolactone), a sesquiterpene lactone extracted from Dittrichia viscosa.

  通过1,3-偶极环加成反应，分别在绒毛膜球蛋白B环（α-亚甲基-γ -丁内酯），一种从粘菌（Dittrichia viscosa）中提取的倍半萜烯内酯。
• Effect of substituents on spin density in benzimidazole nitronyl nitroxide radicals studied by electron spin resonance
  作者：Burak Esat、Ismail Fidan、Sumeyye Bahceci、Yusuf Yerli、Levent Sari

  DOI：10.1002/mrc.2443

  日期：2009.8

  Several novel benzimidazole‐3‐oxide‐1‐oxyl radicals with substituents at 5 and/or 6 position were synthesized. The ESR analysis of nitrogen hyperfine coupling constants (hfccs) revealed that substituents at 5 and 6‐position affect the spin density to greater extent than substituents on the phenyl ring at 2‐position. Density functional theory calculations of nitrogen hfccs were performed using several

  合成了几种在 5 和/或 6 位具有取代基的新型苯并咪唑-3-氧化物-1-氧基。氮超精细耦合常数（hfccs）的 ESR 分析表明，5 位和 6 位的取代基比 2 位苯环上的取代基对自旋密度的影响更大。氮 hfccs 的密度泛函理论计算是使用几种不同的 Pople 型基组，以及局部轨道（IGLO-II、IGLO-III）和电子顺磁共振（EPR-II、EPR- II) 基组。实验和理论 hfcc 进行了比较。版权所有 © 2009 John Wiley & Sons, Ltd.
• Regio- and stereoselective 1,3-dipolar cycloaddition reactions of <i>C</i>-aryl (or hetaryl)-<i>N</i>-phenylnitrones to monosubstituted ylidene malononitriles and 4-benzylidene-2-phenyloxazol-5(4<i>H</i>)-one
  作者：Ramadan A. Mekheimer、Khadijah Al-Zaydi、Mahmoud A. A. Ibrahim、Asma Al-Shamary、Kamal Sadek

  DOI：10.1515/znb-2016-0263

  日期：2017.5.1

  of 1,3-dipolar cycloaddition reactions of C-aryl (or hetaryl)-N-phenylnitrones to monosubstituted ylidene malononitriles and 4-benzylidene-2-phenyl-oxazol-5(4H)-one is described. The reaction of C-(4-(dimethylamino)phenyl)-N-phenyl-nitrone (1a) with 2-(4-substituted-benzylidene)malononitriles 2a, b in dry toluene, in the absence of catalyst, at reflux temperature furnished the novel cycloadducts 2-(3-aryl-2-phenyl-2

  摘要描述了 C-芳基（或杂芳基）-N-苯基硝酮与单取代亚基丙二腈和 4-苄叉-2-苯基-恶唑-5(4H)-酮的 1,3-偶极环加成反应的第一个例子。C-(4-(二甲氨基)苯基)-N-苯基-硝酮(1a)与2-(4-取代-亚苄基)丙二腈2a、b在干燥甲苯中的反应，在没有催化剂的情况下，在回流温度下提供新型环加合物2-(3-芳基-2-苯基-2,3-二氢-1,2,4-恶二唑-5-基)-3-(4-甲氧基苯基)丙烯腈3a、b。在无催化剂的情况下，在无催化剂的情况下，将 C-芳基（或杂芳基）-N-苯基硝酮 1b-i 与 2-（4-甲氧基-亚苄基）丙二腈（2a）回流，得到意想不到的 2-氰基-3-（4 -甲氧基苯基)-丙烯酰胺 (5)，作为唯一产品​​。另一方面，回流 4-benzylidene-2-phenyloxazol-5(4H)-one (7) 与等摩尔量的 C-芳基（或杂芳基）-N-苯基-硝酮 1a-c
• Highly atom efficient synthesis of 2,2,4,5-tetrasubstituted 3(2<i>H</i>)-furanones having both hydroxyl and amino substituents
  作者：Jesna Antony、Sumi P. Musthafa、Rakesh Natarajan、Sindhu Mathai、Karakkattu S. Devaky、John P. Rappai

  DOI：10.1080/00397911.2022.2036347

  日期：2022.2.16

  Abstract We have developed a highly atom efficient synthesis of tetrasubstituted 3(2H)-furanones from easily accessible starting materials such as C,N-diarylaldonitrones and dibenzoylacetylene. Control experiments revealed that reaction of aldonitrones having electron-withdrawing groups on the C-aryl substituent in polar aprotic solvents exhibited high product selectivity while reaction temperature

  摘要 我们已经开发出一种高效的四取代 3(2 H )-呋喃酮合成方法，该合成方法由容易获得的起始材料（如C,N-二芳基醛固酮和二苯甲酰基乙炔）构成。对照实验表明，在C-芳基取代基上具有吸电子基团的醛固酮在极性非质子溶剂中的反应表现出高产物选择性，而反应温度对产物收率和选择性的影响可忽略不计。