o-Nitro-benzamidoxim | 22179-83-5

• 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: o-Nitro-benzamidoxim
• 英文别名: N'-hydroxy-2-nitrobenzenecarboximidamide
• CAS: 22179-83-5
• 化学式: C₇H₇N₃O₃
• 分子量: 181.151
• InChiKey: RZKNXPAYKMNEOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  o-Nitro-benzamidoxim 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 34.0h， 生成 2-(1,2,4-oxadiazol-3-yl)aniline
  参考文献：
  名称：

  COMPOUNDS AND METHODS FOR TREATING CANCER

  摘要：

  提供了替代肉桂酰胺化合物和类似物、制备这类化合物的方法、包含这类化合物的药物组合物和药物、以及使用这类化合物治疗、预防或改善癌症的方法。

  公开号：

  US20200299282A1
• 作为产物：
  描述：

  2-硝基苯甲腈 在 盐酸羟胺 、 三乙胺 作用下， 以 乙醇 为溶剂， 生成 o-Nitro-benzamidoxim
  参考文献：
  名称：

  咪唑盐酸盐促进 3,5-二取代-1,2,4-恶二唑的合成

  摘要：

  咪唑盐酸盐作为添加剂促进酰胺肟和 DMA 衍生物反应生成 3,5-二取代-1,2,4-恶二唑，收率从低到高，无需使用偶联剂、氧化剂、强酸或强碱和其他添加剂。

  DOI：

  10.1016/j.tet.2021.132496

文献信息

• Synthesis of 3,5-disubstituted-1,2,4-oxadiazoles using tetrabutylammonium fluoride as a mild and efficient catalyst
  作者：Anthony R Gangloff、Joane Litvak、Emma J Shelton、David Sperandio、Vivian R Wang、Kenneth D Rice

  DOI：10.1016/s0040-4039(00)02288-7

  日期：2001.2

  Tetrabutylammonium fluoride (TBAF) was found to be a mild and efficient catalyst for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles. Using 0.1–1.0 equivalents of TBAF in THF for 1–24 h at room temperature, alkanoyl- and aroyloxyamidines were converted in high yield to the corresponding 3,5-disubstituted-1,2,4-oxadiazoles. A variety of R and R′ substituents were investigated.

  发现四丁基氟化铵（TBAF）是合成3,5-二取代-1,2,4-恶二唑的温和而有效的催化剂。在室温下，使用THF中的0.1–1.0当量的TBAF，在室温下放置1–24小时，可以将烷酰基-和芳酰氧基am以高收率转化为相应的3,5-二取代-1,2,4-恶二唑。研究了各种R和R'取代基。
• An experimental and theoretical study of reaction mechanisms between nitriles and hydroxylamine
  作者：Attila Vörös、Zoltán Mucsi、Zoltán Baán、Géza Timári、István Hermecz、Péter Mizsey、Zoltán Finta

  DOI：10.1039/c4ob00854e

  日期：——

  The industrially relevant reaction between nitriles and hydroxylamine yielding amidoximes was studied in different molecular solvents and in ionic liquids. In industry, this procedure is carried out on the ton scale in alcohol solutions and the above transformation produces a significant amount of unexpected amide by-product, depending on the nature of the nitrile, which can cause further analytical and purification issues. Although there were earlier attempts to propose mechanisms for this transformation, the real reaction pathway is still under discussion. A new detailed reaction mechanistic explanation, based on theoretical and experimental proof, is given to augment the former mechanisms, which allowed us to find a more efficient, side-product free procedure. Interpreting the theoretical results obtained, it was shown that the application of specific imidazolium, phosphonium and quaternary ammonium based ionic liquids could decrease simultaneously the reaction time while eliminating the amide side-product, leading to the targeted product selectively. This robust and economic procedure now affords a fast, selective amide free synthesis of amidoximes.

  在不同分子溶剂和离子液体中，对腈与羟胺生成脒基肟的工业相关反应进行了研究。在工业上，这一过程在吨级的醇溶液中进行，而上述转化过程会产生大量意外的酰胺副产物，这取决于腈的性质，可能导致进一步的分析和纯化问题。尽管之前有人尝试提出这一转化的机理，但真正的反应途径仍在讨论之中。基于理论和实验证据，给出了一个新的详细反应机理解释，以增强先前的机理，这使我们能够找到一种更高效、无副产物的方法。通过对所获得理论结果的解释，结果显示，使用特定的咪唑鎓、磷鎓和季铵盐基离子液体，不仅可以同时缩短反应时间，还能消除酰胺副产物，从而选择性地得到目标产物。这一稳健且经济的程序现在提供了一种快速、选择性的无酰胺脒基肟合成方法。
• Synthesis and Properties of Energetic 1,2,4-Oxadiazoles
  作者：Zuoquan Wang、Hong Zhang、Farukh Jabeen、Girinath Gopinathan-Pillai、Justin A. Arami、Benjamin J. Killian、Kelcie D. Stiegler、Dalia S. Yudewitz、Pauline L. Thiemann、Jessica D. Turk、Wenfeng Zhou、Peter J. Steel、C. Dennis Hall、Alan R. Katritzky

  DOI：10.1002/ejoc.201501056

  日期：2015.12

  reported and the effects of nitro groups in the aromatic rings on the experimental heats of decomposition (ΔHd) and heats of combustion (ΔHc) are evaluated. Heats of formation (ΔHf) and densities (ρ) were calculated and correlations between ΔHd and ΔHf were assessed for these compounds. Experimental determination of ρ (by gas pycnometry) on a selection of the compounds led to the calculation of detonation

  报道了一系列 3,5-二-芳基-1,2,4-恶二唑的合成和表征，以及芳环中硝基对实验分解热 (ΔHd) 和燃烧热 (ΔHc) 的影响) 进行评估。计算了这些化合物的形成热 (ΔHf) 和密度 (ρ)，并评估了 ΔHd 和 ΔHf 之间的相关性。对选择的化合物进行 ρ（通过气体比重测定法）的实验确定导致通过 Explo 5 程序计算爆速 (VD)、爆压 (PD) 和比冲 (ISP) 参数。化合物 (4i) 的 X 射线分析证实了该结构，并显示出晶体密度（在 120 K 下）与气体比重测定法确定的接近。
• A Convenient Synthesis of 5-Amino-Substituted 1,2,4-Oxadiazole Derivatives via Reactions of Amidoximes with Carbodiimides
  作者：Konstantina C. Fylaktakidou、Maria Ispikoudi、Konstantinos E. Litinas、Konstantina C. Fylaktakidou

  DOI：10.3987/com-08-11340

  日期：——

  one step and in high yields, via reactions of a variety of aryl, benzyl, cycloalkyl and alkyl amidoximes with commercially available carbodiimides. Alkyl carbodiimides reacted with amidoximes in toluene to give 5-alkylamino-1,2,4-oxadiazoles, whereas aromatic carbodiimide reacted in DMF to give initially the intermediate O-amidoxime adducts, which were further cyclized to the corresponding 5-arylamino-1

  通过各种芳基、苄基、环烷基和烷基偕胺肟与市售碳二亚胺的反应，可以在一个步骤中以高产率轻松制备 5-氨基取代的 1,2,4-恶二唑衍生物。烷基碳二亚胺在甲苯中与偕胺肟反应得到 5-烷基氨基-1,2,4-恶二唑，而芳族碳二亚胺在 DMF 中反应最初得到中间体 O-偕胺肟加合物，进一步环化为相应的 5-芳基氨基-1， 2,4-恶二唑。
• Synthesis and antiproliferative efficiency of novel bis(imidazol-1-yl)vinyl-1,2,4-oxadiazoles
  作者：Kebballi N. Nandeesh、Hassan A. Swarup、Nagarakere C. Sandhya、Chakrabhavi D. Mohan、Chottanahalli S. Pavan Kumar、Manikyanahalli N. Kumara、Kempegowda Mantelingu、Sannaiah Ananda、Kanchugarakoppal S. Rangappa

  DOI：10.1039/c5nj02925b

  日期：——

  A new class of bis(imidazol)vinyl-1,2,4-oxadiazoles were synthesised and their anti-proliferative efficiency was tested against HCT116 and A549 cancer cell lines.

  一种新型的双咪唑基乙烯基-1,2,4-噁二唑类化合物被合成，并对其抗增殖效率进行了针对HCT116和A549癌细胞系的测试。