C-(2-nitrophenyl)-N-phenylnitrone | 53548-19-9

• 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-(2-nitrophenyl)-N-phenylnitrone
• 英文别名: N-(2-nitrobenzylidene)aniline oxide；1-(2-nitrophenyl)-N-phenylmethanimine oxide；(2-Nitrophenyl)-N-phenylmethanimine N-oxide
• CAS: 53548-19-9
• 化学式: C₁₃H₁₀N₂O₃
• 分子量: 242.234
• InChiKey: CDRLDPPEUGIHML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-(2-nitrophenyl)-N-phenylnitrone 、 亚苯甲基丙二酸二乙酯 在 (2S)-N-tert-butyl-1-[3-[(2S)-2-(tert-butylcarbamoyl)-1-oxidopiperidin-1-ium-1-yl]propyl]-1-oxidopiperidin-1-ium-2-carboxamide 、 nickel(II) perchlorate hexahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到diethyl 2,5-diphenyl-3-(o-nitro-phenyl)-4,4-isoxazolidine-dicarboxylate
  参考文献：
  名称：

  硝基到丙二酸丙二酸酯的催化不对称1,3-偶极环加成反应：高度对映选择性合成多取代的异恶唑烷

  摘要：

  一切尽在掌握！硝酮，以亚烷基丙二酸酯的阿不对称催化的1,3-偶极环加成反应，通过手性催化Ñ，Ñ '二氧化物-镍（CLO 4）2 ⋅ 6 H 2 ö配合物，已经开发了具有优良的产率，diastereo-，和对映选择性（参见方案，R 1＝芳基，R 2＝烷基，R 3，R 4＝ Ph）。此外，还提出了一种可能的过渡态，以阐明高水平的对映和非对映控制。

  DOI：

  10.1002/chem.201100053
• 作为产物：
  描述：

  硝基苯 在 氯化铵 、 锌 作用下， 以 氯仿 、 水 为溶剂， 反应 1.25h， 生成 C-(2-nitrophenyl)-N-phenylnitrone
  参考文献：
  名称：

  Synthesis and Evaluation of Novel 5-cyclohexyl-2-(4″-substitutedphenyl)-3-(2″-substitutedphenyl)4H-2,3,3a,5,6,6a-hexahydropyrrolo[3,4-d]isoxazole-4,6-dione Derivatives for TheirIn VitroAntioxidant and Antibacterial Activities

  摘要：

  1,3‐Dipolar cycloaddition reactions of N‐cyclohexyl maleimide (1) with azomethine N‐oxide (2) have afforded novel isoxazolidine (3) in excellent yield. Their structures have been characterized from their IR, 1H‐NMR, 13C‐NMR, 1H,1H‐COSY, MS(ESI), and elemental analysis techniques. In vitro antibacterial activity of the synthesized compounds were investigated against a representative panel of pathogenic strains specifically two Gram‐positive bacteria (Staphylococcus aureus and Streptococcus pyogenes) and two Gram‐negative bacteria (Pseudomonas aeruginosa and Escherichia coli) using agar‐well diffusion assay. Some of the compounds (3a, 3k, 3n, and 3o) exhibited promising antibacterial activities. All the synthesized compounds have also been screened for their antioxidant activities and were found to be significantly active.

  DOI：

  10.1002/jhet.2543

文献信息

• Catalytic Diastereo- and Enantioselective Synthesis of 2-Imidazolinones
  作者：Pablo Martínez-Pardo、Gonzalo Blay、Alba Escrivá-Palomo、Amparo Sanz-Marco、Carlos Vila、José R. Pedro

  DOI：10.1021/acs.orglett.9b01244

  日期：2019.6.7

  Chiral cyclic ureas (2-imidazolinones) were prepared by the reaction of nitrones and isocyanoacetate esters using a multicatalytic system that combines a bifunctional Brønsted base–squaramide organocatalyst and Ag+ as a Lewis acid. The reaction could be achieved with a range of nitrones derived from aryl- and cycloalkylaldehydes with moderate diastereo- and good enantioselectivity. A plausible mechanism

  手性环状脲（2-咪唑啉酮）是由硝酮与异氰基乙酸酯反应制得的，采用的是一种多催化体系，该体系结合了双功能的布朗斯台德碱-方酰胺有机催化剂和作为路易斯酸的Ag +。该反应可以用一系列衍生自芳基-和环烷基醛的，具有中等非对映选择性和良好对映选择性的硝酮来完成。提出了一种可行的机理，其中涉及将硝酮和异氰基乙酸酯进行最初的正式[3 + 3]环加成，然后重排成氨基异氰酸酯并环化成咪唑啉酮。
• Rhodium(II)- and Copper(II)-Catalyzed Reactions of Enol Diazoacetates with Nitrones: Metal Carbene versus Lewis Acid Directed Pathways
  作者：Yu Qian、Xinfang Xu、Xiaochen Wang、Peter J. Zavalij、Wenhao Hu、Michael P. Doyle

  DOI：10.1002/anie.201202525

  日期：2012.6.11

  A complimentary cat.: Copper(II) hexafluoroantimonate catalyzes the formal [3+3] cycloaddition of Lewis acid activated nitrones and vinyl diazoacetates to produce 3,6‐dihydro‐1,2‐oxazines in yields of up to 96 % and diastereoselectivities greater than 25:1 (see scheme). This process compliments the metal carbene pathway that is catalyzed by rhodium(II) species.

  一只免费的猫。：六氟锑酸铜（II）催化路易斯酸活化的硝酮和乙烯基重氮乙酸酯的正式[3 + 3]环加成反应，生成3,6-二氢-1,2-恶嗪，收率高达96％，非对映选择性大于25：1 （请参阅方案）。此过程补充了铑（II）物种催化的金属卡宾途径。
• 1,3-dipolar cycloaddition reactions of 2-substituted azomethine N-oxides with N-benzyl maleimides leading to the synthesis of stereoisomers
  作者：Rahul Badru、Sakshi Shah、Baldev Singh

  DOI：10.1002/jhet.794

  日期：2012.3

  The azomethine N‐oxides (1) on reacting with N‐benzylmaleimide (2) provide a mixture of stereoisomers 2,3‐diphenyl‐5‐benzyl‐4H‐2,3,3a,5,6,6a‐hexahydropyrrolo[3,4‐d]isoxazole‐4,6–dione derivatives (3) in good yields. These isomers have been assigned cis and trans configurations (3‐A and 3‐B) with respect to proton C3‐H on the azomethinic carbon on the basis of their PMR and H‐NMR COSY data. The ratio

  与N-苄基马来酰亚胺（2）反应时，偶氮甲碱N-氧化物（1）提供了立体异构体2,3-二苯基-5-苄基4 H -2,3,3a，5,6,6a-六氢吡咯[3]的混合物，4 - d ]异恶唑-4,6-二酮衍生物（3），收率高。根据其PMR和H-NMR COZY数据，已将这些异构体相对于偶氮二甲基碳上的质子C 3 -H分配了顺式和反式构型（3-A和3-B）。发现顺式和反式异构体之间的比例取决于存在于C的邻位的取代基-苯基醛基部分。这些1,3-偶极环加成反应的显着特征在于，N-苄基部分上的苄基质子遭受宝石耦合，表明磁性不等价。J.杂环化​​学。，（2012）。
• Synthesis of Benzimidazolones via One-Pot Reaction of Hydroxylamines, Aldehydes, and Trimethylsilyl Cyanide Promoted by Diacetoxyiodobenzene
  作者：Huaiyuan Zhang、Danfeng Huang、Ke-Hu Wang、Jun Li、Yingpeng Su、Yulai Hu

  DOI：10.1021/acs.joc.6b02781

  日期：2017.2.3

  A novel and efficient PhI(OAc)2-promoted one-pot reaction of aromatic hydroxylamines, aldehydes, and TMSCN in the presence of BF3·Et2O is described. A wide variety of N-substituted benzimidazolones are obtained with satisfactory yields under mild reaction conditions. The method was proven to be efficient for the synthesis of benzimidazolone derivatives from readily available starting materials.

  描述了在BF 3 ·Et 2 O的存在下新型有效的由PhI（OAc）2促进的芳族羟胺，醛和TMCSN的单锅反应。在温和的反应条件下以令人满意的产率获得了多种N-取代的苯并咪唑酮。事实证明，该方法对于从容易获得的起始原料合成苯并咪唑酮衍生物是有效的。
• A facile, regio and diastereoselective synthesis of functionalized azetidin-2-ones: Cu(I) mediated Kinugasa reaction of functionalized nitrones with acetylenic alcohols
  作者：Priyanka Sharma、Dinesh Mahajan、Vipan Kumar、Rupesh Kumar、Gaurav Bhargava

  DOI：10.1080/00397911.2024.2321596

  日期：2024.4.2

  The manuscript presents an efficient method for the synthesis of various cis-azetidin-2-ones with high regio- and diastereoselectivity. This approach utilizes Kinugasa reaction involving diverse fu...

  该手稿提出了一种合成具有高区域和非对映选择性的各种顺式氮杂环丁烷-2-酮的有效方法。该方法利用涉及多种功能的衣笠反应...