4-methyl-1,2,5-oxadiazole-3-carbonitrile 5-oxide | 50882-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-methyl-1,2,5-oxadiazole-3-carbonitrile 5-oxide
• 英文别名: 4-cyano-3-methylfuroxan；4-methyl-5-oxy-furazan-3-carbonitrile；4-Methyl-5-oxido-1,2,5-oxadiazol-5-ium-3-carbonitrile
• CAS: 50882-09-2
• 化学式: C₄H₃N₃O₂
• 分子量: 125.087
• InChiKey: ZODQMVCSTLQTIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-1,2,5-oxadiazole-3-carbonitrile 5-oxide 在 一水合肼 作用下， 以 异丙醇 为溶剂， 生成 4-methyl-1,2,5-oxadiazole-3-carbohydrazonamide 5-oxide
  参考文献：
  名称：

  通过（1,2,4-triazin-3-yl） 呋喃聚糖的串联杂Diels-Alder / retro-Diels-Alder反应设计具有呋喃喃嘧啶核的杂合杂环系统†

  摘要：

  两种方便，简便，区域选择性和高效的一锅操作方案，用于根据裁缝的串联反电子需求异Diels-Alder / Retro-Diels-Alder反应，合成具有呋喃唑啉核心的先前未知的杂化杂环系统已经开发了具有1-（吡咯烷基）环己烯和降冰片二烯的（1,2,4-三嗪-3-基）呋喃酮。该方法包括将烯胺或降冰片二烯[4 + 2]环加成到（1,2,4-三嗪-3-基）呋喃酮的1,2,4-三嗪环上，然后一锅转化形成的中间体，并且可以通过一个C–C键在一个分子中将呋喃喃和吡啶（四氢异喹啉，茚并吡啶，三联吡啶）环相结合，形成一系列广泛的多杂环合簇，收率好至极好。

  DOI：

  10.1039/c6ra05110c
• 作为产物：
  描述：

  3-Methyl-4-furoxancarbonsaeureamid 在 吡啶 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到4-methyl-1,2,5-oxadiazole-3-carbonitrile 5-oxide
  参考文献：
  名称：

  An efficient access to (1H-tetrazol-5-yl)furoxan ammonium salts via a two-step dehydration/[3+2]-cycloaddition strategy

  摘要：

  A general, highly effective two-step approach for direct synthesis of (1H-tetrazol-5-yl)furoxan ammonium salts with various functional substituents based on initial effective synthesis of cyanofuroxans by dehydration of furoxancarboxylic acid amides by the action of (CF3CO)(2)O/Py followed by [3+2]-cycloaddition of cyanofuroxans to ammonium azide, generated in situ from TMSN3 and NH4F, has been developed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.07.034

文献信息

• Synthesis, structural characterization and cytotoxic activity of heterocyclic compounds containing the furoxan ring
  作者：Alexander S. Kulikov、Alexander A. Larin、Leonid L. Fershtat、Lada V. Anikina、Sergey A. Pukhov、Sergey G. Klochkov、Marina I. Struchkova、Anna A. Romanova、Ivan V. Ananyev、Nina N. Makhova

  DOI：10.24820/ark.5550190.p010.229

  日期：——

  A direct approach to the synthesis of previously unknown 1H-1,2,3-triazolylfuroxans, involving nucleophilic substitution of the nitro group in nitrofuroxans followed by catalytic [3+2] cycloaddition of intermediate azidofuroxans to 1,3-ketoesters, is reported. The scope of the triazolylfuroxans was additionally diversified through a number of transformations of the functional groups attached to the

  报道了一种合成以前未知的 1H-1,2,3-三唑基呋喃的直接方法，包括对硝基呋喃中硝基进行亲核取代，然后将中间体叠氮呋喃催化 [3+2] 环加成生成 1,3-酮酯。通过连接到 1,2,3-三唑环上的官能团的大量转化，三唑基呋喃的范围进一步多样化。研究了新合成的三唑基呋喃和先前报道的杂芳基呋喃的细胞毒活性。使用分光光度计技术通过格里斯反应测量所选合成杂芳基呋喃的 NO 供体能力。
• Efficient assembly of mono- and bis(1,2,4-oxadiazol-3-yl)furoxan scaffolds via tandem reactions of furoxanylamidoximes
  作者：Leonid L. Fershtat、Ivan V. Ananyev、Nina N. Makhova

  DOI：10.1039/c5ra07295f

  日期：——

  effective one-pot protocol for the synthesis of new types of heterocyclic systems incorporating mono- and bis(1,2,4-oxadiazol-3-yl)furoxan cores based on the tandem heterocyclization of furoxanylamidoximes with various aliphatic, aromatic, and heterocyclic carboxylic acid chlorides under very mild conditions (Cs2CO3, MeCN, 20 °C) has been developed. In addition, a solvent-free approach for the (1,2,4-oxadiazol-3-yl)furoxan

  一种通用，简便，高效的一锅操作规程，用于基于呋喃西酰胺基肟与各种脂肪族化合物的串联杂环化反应，合成掺入单和双（1,2,4-恶二唑-3-基）呋喃核的新型杂环系统，已经开发了在非常温和的条件下（Cs 2 CO 3，MeCN，20°C）的芳族和杂环羧酸氯化物。此外，已经实现了一种无溶剂的方法，该方法用于通过呋喃酰胺基肟与Sc（OTf）3催化的原甲酸三甲酯反应合成（1,2,4-恶二唑-3-基）呋喃。步骤经济和作用范围的优势使这些反应成为组装具有通用化学和生物医学兴趣的杂环支架的强大工具。
• Regioselective synthesis of bifuroxanyl systems with the 3-nitrobifuroxanyl core via a one-pot acylation/nitrosation/cyclization cascade
  作者：Leonid L. Fershtat、Alexander A. Larin、Margarita A. Epishina、Alexander S. Kulikov、Igor V. Ovchinnikov、Ivan V. Ananyev、Nina N. Makhova

  DOI：10.1016/j.tetlet.2016.08.011

  日期：2016.9

  3-nitrobifuroxanyl core, based on a cascade of one-pot reactions comprising of the acylation of dinitromethane sodium salt with furoxanyl hydroxamic acid chlorides, nitrosation of the acylation product with NaNO2/AcOH/AcONa, and intramolecular cyclization of the nitrosation product to give the 3-nitrobifuroxanyl moiety, has been developed.

  基于一锅反应的级联反应，用于合成先前未知的包含3-硝基联呋喃基核心的联呋喃基系统的区域选择性方法，该反应包括二硝基甲烷钠盐与呋喃基异羟肟酸氯化物的酰化，酰化产物与NaNO 2 /的亚硝化已经开发了AcOH / AcONa，以及亚硝化产物的分子内环化以生成3-硝基联呋喃基基团部分。
• 1,2,5-Oxadiazole N-oxide derivatives as potential anti-cancer agents: synthesis and biological evaluation. Part IV
  作者：M Boiani

  DOI：10.1016/s0223-5234(01)01265-x

  日期：2001.10

  Several new 1,2,5-oxadiazole N-oxide derivatives and some deoxygenated analogues were synthesized to be tested as potential selective hypoxic cell cytotoxins. Compounds prepared were designed in order to gain insight into the mechanism of action of this kind of cytotoxin. Compounds were tested in oxia and hypoxia and they proved to be non-selective. 3-Cyano-N(2)-oxide-4-phenyl-1,2,5-oxadiazole showed

  合成了几种新的1,2,5-恶二唑N-氧化物衍生物和一些脱氧类似物，作为潜在的选择性低氧细胞毒素进行了测试。设计制备的化合物是为了深入了解这种细胞毒素的作用机理。在缺氧和缺氧状态下测试了化合物，事实证明它们是非选择性的。3-氰基-N（2）-氧化物-4-苯基-1,2,5-恶二唑显示出最佳的细胞毒性活性。这些衍生物观察到的细胞毒性可以用1,2,5-恶二唑取代基的电子特性来解释。对细胞毒性更高的衍生物进行了电化学和ESR研究。
• An effective synthesis of (1Н-1,2,4-triazol-3-yl)furoxans
  作者：Leonid L. Fershtat、Margarita A. Epishina、Igor V. Ovchinnikov、Vadim V. Kachala、Nina N. Makhova

  DOI：10.1007/s10593-015-1771-9

  日期：2015.8

  A general, simple, and effective method has been developed for the preparation of previously practically unknown (5-R-1De-1,2,4-triazol-3-yl)furoxans with various substituents at the other carbon atom of furoxan ring, based on condensation of furoxanylamidrazones with electrophilic reagents (cyanogen bromide, acetic and trifluoroacetic anhydrides).