(m-nitrobenzylidene)-p-bromoaniline | 3489-08-5

• 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: (m-nitrobenzylidene)-p-bromoaniline
• 英文别名: N-<3-Nitro-benzyliden>-4-brom-anilin；<3-Nitro-benzyliden>-<4-brom-anilin>；4-bromo-N-(3-nitro-benzyliden)-aniline；3-Nitro-benzaldehyd-(4-brom-anil)；4-Brom-N-(3-nitro-benzyliden)-anilin；(4-Bromo-phenyl)-(3-nitro-benzylidene)-amine；N-(4-bromophenyl)-1-(3-nitrophenyl)methanimine
• CAS: 3489-08-5
• 化学式: C₁₃H₉BrN₂O₂
• 分子量: 305.131
• InChiKey: JNPQOPFDCXXMSZ-UHFFFAOYSA-N

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：

  (m-nitrobenzylidene)-p-bromoaniline 在 三氟化硼乙醚 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 120.0h， 生成 [1-(N-p-bromophenylamino)]-1-(m-nitrophenyl)methylphosphonous acid borane diisopropyl ester
  参考文献：
  名称：

  在膦酸酯和膦酸酯衍生物中存在P–O和P–N键的情况下，P = O键的化学选择性还原

  摘要：

  使用市售BH 3络合物，无需伴随其酯键和酰胺键的断裂即可实现α-羟基和α-氨基膦酸/次膦酸衍生物中P = O键的化学选择性还原。还原涉及通过近端的OH或NH基团的分子内协助，从而能够优先去除磷酰氧。

  DOI：

  10.1002/ejoc.201801518
• 作为产物：
  描述：

  间硝基苯甲醛 、 4-溴苯胺 以 甲苯 为溶剂， 反应 48.0h， 以59%的产率得到(m-nitrobenzylidene)-p-bromoaniline
  参考文献：
  名称：

  在膦酸酯和膦酸酯衍生物中存在P–O和P–N键的情况下，P = O键的化学选择性还原

  摘要：

  使用市售BH 3络合物，无需伴随其酯键和酰胺键的断裂即可实现α-羟基和α-氨基膦酸/次膦酸衍生物中P = O键的化学选择性还原。还原涉及通过近端的OH或NH基团的分子内协助，从而能够优先去除磷酰氧。

  DOI：

  10.1002/ejoc.201801518

文献信息

• A Convenient and Facile Synthesis of New Thiazole Derivatives
  作者：Eman A. El Rady

  DOI：10.1080/10426500701724522

  日期：2008.6.9

  catalytic amount of triethyl-amine afforded new polysubstituted thiazolo[4,5-c]pyrazole, thiazolo[4,5-d]-pyrimidine, thiazolo[4,5-b]-pyridine, thiazolo[4,5-b][1,5]benzodiazepine, thiazolo[4,5-b] [1,5]benzoxazepine, thiazolo[4′, 5′:6,5]-pyrimido[1,2-b][1,2,4]triazole and thiazolo[4′, 5′:6,5]pyrimido[1,2-b]pyrazole derivatives in good yields. The structure of the new compounds were confirmed based on IR, 1

  4-Chloro-2,3-dihydrothiazole-5-carboxaldehyde 与一些亲核试剂反应，如水合肼、苯肼、尿素、硫脲、氨基脲、氰基乙酰胺、氰硫基乙酰胺、氰基乙酰肼、2-苯二胺、2-氨基苯酚在催化量的三乙胺存在下，氨基[1,2,4]三唑和3-氨基吡唑在乙醇溶液中回流，得到新的多取代噻唑并[4,5-c]吡唑，噻唑并[4,5-d]-嘧啶、噻唑并[4,5-b]-吡啶、噻唑并[4,5-b][1,5]苯二氮卓类、噻唑并[4,5-b] [1,5]苯并恶氮杂、噻唑并[4,5-b][1,5] :6,5]-嘧啶并[1,2-b][1,2,4]三唑和噻唑并[4', 5':6,5]嘧啶并[1,2-b]吡唑衍生物产率良好。基于IR、 1 H-, 13 C-NMR、质谱和元素分析确认了新化合物的结构。
• Nisbet, Journal of the Chemical Society, 1928, p. 3124
  作者：Nisbet

  DOI：——

  日期：——
• Ingold; Piggott, Journal of the Chemical Society, 1922, vol. 121, p. 2799
  作者：Ingold、Piggott

  DOI：——

  日期：——
• 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.
• Imino Diels-Alder Reactions: Efficient Synthesis of 2-Aryl-4-(2′-oxopyrrolidinyl-1′)-1,2,3,4-tetrahydroquinolines catalyzed by Antimony(III) Sulfate
  作者：Aswathanarayana Srinivasa、Kittappa M. Mahadevan、Vijaykumar Hulikal

  DOI：10.1007/s00706-007-0777-0

  日期：2008.3

  Antimony(III) sulfate is found to catalyze the imino Diels-Alder reaction of Schiff's bases with N-vinylpyrrolidin-2-one to afford 2-aryl-4-(2'-oxopyrrolidinyl-1')-1,2,3,4-tetrahydroquinolines. One-pot synthesis of 1,2,3,4-tetrahydroquinolines from 3-nitro benzaldehyde and aromatic amines with N-vinylpyrrolidin-2-one catalyzed by antimony(III) sulfate is also reported. This catalyst is inexpensive, easily available, and it was also found that catalyst could be recovered quantitatively and reused without much loss of catalytic activity.