1-(4-氯苯基)-N-(3-硝基苯基)甲亚胺 | 10480-29-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(4-氯苯基)-N-(3-硝基苯基)甲亚胺
• 英文名称: (4-Chlor-benzyliden)-(3-nitro-anilin)
• 英文别名: N-(4-Chlor-benzyliden)-3-nitro-anilin；p-Chlorobenzylidene-(3-nitrophenyl)-amine；1-(4-chlorophenyl)-N-(3-nitrophenyl)methanimine
• CAS: 10480-29-2
• 化学式: C₁₃H₉ClN₂O₂
• 分子量: 260.68
• InChiKey: JSLHZGWGZRIVLW-UHFFFAOYSA-N

物化性质

• 熔点：
  124.0-125.5 °C
• 沸点：
  410.0±30.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)
• 保留指数：
  2428

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-氯苯基)-N-(3-硝基苯基)甲亚胺 在 吡啶 、 溶剂黄146 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 0.97h， 生成 3-(4-chlorophenyl)-4-imino-5-phenyl-2-(3-nitrophenyl)-2H,3H,5H-[1,2,5]thiadiazolidin-1-oxide
  参考文献：
  名称：

  Synthesis of 4-Imino-2H,3H,5H-[1,2,5]thiadiazolidin-1-oxide through Cycloaddition Reaction of N-Sulphinylanilines and N-(α-Cyano-α-aryl)-methylanilines

  摘要：

  Through the normal mode of cycloaddition reaction of N‐(α‐cyano‐α‐aryl)‐methylanilines (II) onto N‐sulphinylanilines (III) has provided 2,3,5‐triaryl‐4‐imino‐2H,3H,5H‐[1,2,5]thiadiazolidin‐1‐oxides (IV). The present protocol has advantage of convenient operation to synthesize heterocyclics in good yield.

  DOI：

  10.1002/jhet.1828
• 作为产物：
  描述：

  4-氯苯甲醛 、 间硝基苯胺 以 乙醇 为溶剂， 生成 1-(4-氯苯基)-N-(3-硝基苯基)甲亚胺
  参考文献：
  名称：

  Synthesis of 4-Imino-2H,3H,5H-[1,2,5]thiadiazolidin-1-oxide through Cycloaddition Reaction of N-Sulphinylanilines and N-(α-Cyano-α-aryl)-methylanilines

  摘要：

  Through the normal mode of cycloaddition reaction of N‐(α‐cyano‐α‐aryl)‐methylanilines (II) onto N‐sulphinylanilines (III) has provided 2,3,5‐triaryl‐4‐imino‐2H,3H,5H‐[1,2,5]thiadiazolidin‐1‐oxides (IV). The present protocol has advantage of convenient operation to synthesize heterocyclics in good yield.

  DOI：

  10.1002/jhet.1828

文献信息

• A catalysis study of mesoporous MCM-41 supported Schiff base and CuSO4·5H2O in a highly regioselective synthesis of 4-thiazolidinone derivatives from cyclocondensation of mercaptoacetic acid
  作者：Hai-Xia Pang、Yong-Hai Hui、Kui Fan、Xue-Jian Xing、Yang Wu、Jing-Hui Yang、Wei Shi、Zheng-Feng Xie

  DOI：10.1016/j.cclet.2015.10.029

  日期：2016.3

  Mesoporous MCM-41 supported Schiff base and CuSO4·5H2O shows high catalytic activity in the cyclocondensation of mercaptoacetic acid with imines (or aldehydes and amines) to afford pharmaceutically important thiazolidinone derivatives. The catalytic reactions involving two-components or three-components afforded the desired product in high yields (up to 98% and 99%). Moreover, the catalyst works well

  MCM-41介孔负载的席夫碱和CuSO4·5H2O在巯基乙酸与亚胺（或醛和胺）的环缩合反应中显示出高催化活性，从而提供了重要的噻唑烷酮衍生物。涉及二组分或三组分的催化反应以高收率（高达98％和99％）提供了所需的产物。此外，该催化剂在可回收性方面效果很好，经过六次回收后，产品的收率分别为85％和83％。
• Application of magnetic Fe₃O₄nanoparticles as a reusable heterogeneous catalyst in the synthesis of β-lactams containing amino groups
  作者：Aleme Moslehi、Maaroof Zarei

  DOI：10.1039/c9nj02759a

  日期：——

  The catalytic activity of magnetic Fe₃O₄nanoparticles to promote the reduction of β-lactams containing nitroaryl groups to β-lactams containing aminoaryl groups in ethanol was reported. This methodology is convenient and green.

  磁性Fe3O4纳米颗粒在乙醇中促进含硝基芳基的β-内酰胺类化合物还原为含氨基芳基的β-内酰胺类化合物的催化活性被报道。这种方法方便且环保。
• REGIOSELECTIVE SYNTHESIS OF 1,2-DIARYLBENZAZETIDENES VIA [2 + 2] CYCLOADDITION REACTIONS OF BENZYNE WITH AZOMETHINES
  作者：Kewal Krishan Singal、Jaswinder Kaur

  DOI：10.1081/scc-100105330

  日期：2001.1

  [2 + 2] Cycloaddition reactions of benzyne generated in situ with various substituted azomethines have been carried out leading to the synthesis of 1,2-diarylbenzazetidenes in good yields with a high degree of regioselectivity.

  [2 + 2] 原位生成的苄与各种取代的偶氮甲碱的环加成反应已经进行，导致以高产率和高度区域选择性合成 1,2-二芳基苯并氮杂环。
• Novel Benzotriazole‐<i>β</i>‐lactam Derivatives as Antimalarial Agents: Design, Synthesis, Biological Evaluation and Molecular Docking Studies
  作者：Malihe Aye、Aliasghar Jarrahpour、Zahra Haghighijoo、Roghayeh Heiran、Roya Pournejati、Hamid Reza Karbalaei‐Heidari、Veronique Sinou、Jean Michel Brunel、Mehmet Akkurt、Namık Özdemir、Edward Turos

  DOI：10.1002/cbdv.202301745

  日期：2024.2

  ketene-imine cycloaddition reaction was employed. First, The reaction of 1H-benzo[d][1,2,3]triazole with 2-bromoacetic acid in aqueous sodium hydroxide yielded 2-(1H-benzo[d][1,2,3]triazol-1-yl)acetic acid. Then, the treatment of 2-(1H-benzo[d][1,2,3]triazol-1-yl)acetic acid with tosyl chloride, triethyl amine, and Schiff base provided new β-lactams in good to moderate yields.The formation of all cycloadducts

  世界各地有许多人患有疟疾，特别是在热带或亚热带地区。虽然疟疾药物在治疗疟疾方面取得了成功，但仍然存在对这些药物产生耐药性的问题。在此，我们以2-(1 H-苯并[ d ][1,2,3]三唑-1-基)乙酸为关键中间体，设计并合成了一些结构新颖的苯并三唑-β-内酰胺。为了合成目标分子，采用了乙烯酮-亚胺环加成反应。首先，1 H-苯并[ d ][1,2,3]三唑与2-溴乙酸在氢氧化钠水溶液中反应，得到2-( 1H-苯并[ d ][1,2,3]三唑-1 -基)乙酸。然后，用甲苯磺酰氯、三乙胺和席夫碱处理 2-(1 H-苯并[ d ][1,2,3]三唑-1-基)乙酸，以良好到中等的收率提供了新的β-内酰胺所有环加合物的形成均通过元素分析、FT-IR、NMR 和质谱数据证实。此外，X射线晶体学用于确定4a化合物的相对立体化学。对每种化合物进行了针对恶性疟原虫K1 的体外抗疟活性测试。 IC 50值范围为
• Triazolines. XXIX. 1,5-diaryl-Δ²-1,2,3-triazolines as aphicides: Mechanism of action via aziridine formation
  作者：Pankaja K. Kadaba

  DOI：10.1002/ps.2780420407

  日期：1994.12

  AbstractThe aphicidal activity of 21 different 1,5‐diphenyl‐Δ2‐1,2,3‐triazolines, conveniently prepared utilizing the catalytic effect of water on the 1,3‐cyclo‐addition of diazomethane to Schiff bases in aqueous dioxane, was evaluated. Triazolines bearing an o‐Cl substituent on the C‐phenyl, either alone (4) or in combination with a m‐ and/or a p‐substituent on the N‐phenyl (14, 15, 17 and 18), showed significant activity, with a combined m‐, p‐ substitution on the N‐phenyl the most effective (17 and 18). While an o‐Cl substituent led to greater activity than an o‐NO2 group, the introduction of an additional p‐Cl substituent on the C‐phenyl eliminated activity (21).The aphicidal activity of triazoline 18 was found to be dependent on the presence of UV light. Since fluorescent lighting used in the testing procedure contains UV light and since triazolines undergo photolysis when exposed to UV light to yield aziridines, it was logical to conclude that the aphicidal activity of the triazolines was, in fact, derived from the aziridines formed during the testing procedure. This mechanism of action was confirmed by preparing the aziridines 22, 23 and 24 corresponding to the active triazolines 14, 15 and 18, and showing that they possessed aphicidal activity equal to or better than that of the triazolines, and by the activity observed in several other structurally related aziridine analogues (25–28). Unlike aziridinyl phosphorous compounds, the aziridines described here are not mutagenic in the Ames assay and thus afford a safer class of pesticides.