4-nitrofuroxan-3-carboxamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-nitrofuroxan-3-carboxamide
• 英文别名: 4-nitro-2-oxido-1,2,5-oxadiazol-2-ium-3-carboxamide
• 化学式: C₃H₂N₄O₅
• 分子量: 174.073
• InChiKey: BEUGVHNATMZCDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 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：
  140
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-nitrofuroxan-3-carboxamide 在 phosphorus pentoxide 作用下， 反应 0.5h， 以48%的产率得到4-cyano-4-nitrofuroxan
  参考文献：
  名称：

  摘要：

  A convenient preparative method was developed for the synthesis of 4-amino-3-furoxancarboxylic acid azide, which is a universal synthon for the preparation of functional furoxan derivatives. This method was used for preparing new azo-, azoxy-, azido-, cyano-, nitro-, carbonylamino-, and hydroxylamino-substituted furoxan derivatives, which have earlier been difficultly accessible.

  DOI：

  10.1023/a:1026073108494
• 作为产物：
  描述：

  4-氨基-1,2,5-恶二唑-3-甲腈2-氧化物 在 sodium tungstate (VI) dihydrate 、 硫酸 、 双氧水 作用下， 以61%的产率得到4-nitrofuroxan-3-carboxamide
  参考文献：
  名称：

  硝基、氰基和甲基呋喃及其双衍生物：从绿色初级炸药到熔铸炸药

  摘要：

  在目前的工作中，我们详细研究了 1,2,5-恶二唑-2-氧化物（呋喃）的 20 种硝基、氰基和甲基衍生物的热化学、热稳定性、机械敏感性和爆轰性能。他们的二元衍生物。对于所有研究的物种，我们还使用高度准确的多级程序 W2-F12 和/或 W1-F12 结合原子化能量方法和等线反应确定了气相形成焓的可靠值。耦合簇技术的轨道 (DLPNO) 修改。除此之外，我们还提出了呋喃烷及其许多（偶氮）双衍生物的形成焓的可靠基准值。此外，我们还报告了以前未知的 3-cyano-4-nitrofuroxan 的晶体结构。在单环化合物中，呋喃的 3-硝基-4-环丙基和二氰基衍生物优于基准熔铸炸药三硝基甲苯，表现出良好的热稳定性（分解温度 >200°C）和对机械刺激不敏感，同时具有显着的挥发性和低熔点。反过来，4,4'-偶氮双-二氨基甲酰基呋喃烷被提议作为四硝酸季戊四醇酯的替代品，这是一种基准的强炸药。最后，3,

  DOI：

  10.3390/molecules25245836
• 作为试剂：
  描述：

  5-Propyl-5H-[1,2,4]triazino[5,6-b]indole-3-thiol 在 4-nitrofuroxan-3-carboxamide 作用下， 以 乙腈 为溶剂， 反应 0.84h， 以63%的产率得到1,2-bis(5-propyl-5H-[1,2,4]triazino[5,6-b]indol-3-yl)disulfane
  参考文献：
  名称：

  亲核取代硝基呋喃烷中的硝基被杂环硫醇和羟基衍生物合成，从而合成杂芳基硫烷基和杂芳氧基呋喃*

  摘要：

  我们报告了一种合成方法，该方法基于4-呋喃呋喃中的硝基被HetS和HetO基团通过与杂芳硫醇和羟基的反应引入的亲核取代，合成了包含呋喃和S-和О-桥连接的杂环片段的未知未知杂环系统1,8-二氮杂双环[5.4.0] undec-7-ene /МеCN系统中的室温杂环。我们表明，杂芳硫醇与在环С-3原子上包含脂肪族，苄基和芳族取代基的4-硝基呋喃喃反应，从而获得了以前未知的杂芳基硫烷基呋喃烷的文库，而仅在4-情况下与羟基杂环的反应才成功硝基-3-苯基呋喃喃，其余的硝基呋喃烷显示低的反应性，并且仅在某些情况下可以获得取代产物。2，CONH 2）起氧化剂作用，形成1,2-二（杂芳基）二硫化物。

  DOI：

  10.1007/s10593-015-1678-5

文献信息

• 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。
• Phenylsulfonylfuroxans as Modulators of Multidrug-Resistance-Associated Protein-1 and P-Glycoprotein
  作者：Roberta Fruttero、Marco Crosetti、Konstantin Chegaev、Stefano Guglielmo、Alberto Gasco、Francesco Berardi、Mauro Niso、Roberto Perrone、Maria Antonietta Panaro、Nicola Antonio Colabufo

  DOI：10.1021/jm100066y

  日期：2010.8.12

  A series of furoxan derivatives were studied for their ability to interact with P-gp and MRP1 transporters in MDCK cells overexpressing these proteins. 3-Phenylsulfonyl substituted furoxans emerged as the most interesting compounds. All of them were capable of inhibiting P-gp, and a few also were capable of inhibiting MRP1. Substituents at the 4-position of 3-phenylsulfonylfuroxan scaffold were able to modulate the selectivity and the intensity of inhibition. In some cases, they reverted MRP1 inhibitor activity, namely, they were capable of potentiating MRP1 dependent efflux. When compounds 16 and 17 were coadministered with doxorubicin, they restored a high degree of the activity of the antibiotic. Preliminary immunoblotting studies carried out on these two compounds indicate that they are capable of nitrating P-gp, which in this form is likely unable to efflux the antibiotic.
• ——
  作者：A. S. Kulikov、I. V. Ovchinnikov、S. I. Molotov、N. N. Makhova

  DOI：10.1023/a:1026073108494

  日期：——

  A convenient preparative method was developed for the synthesis of 4-amino-3-furoxancarboxylic acid azide, which is a universal synthon for the preparation of functional furoxan derivatives. This method was used for preparing new azo-, azoxy-, azido-, cyano-, nitro-, carbonylamino-, and hydroxylamino-substituted furoxan derivatives, which have earlier been difficultly accessible.
• An efficient access to (1H-tetrazol-5-yl)furoxan ammonium salts via a two-step dehydration/[3+2]-cycloaddition strategy
  作者：Leonid L. Fershtat、Margarita A. Epishina、Alexander S. Kulikov、Igor V. Ovchinnikov、Ivan V. Ananyev、Nina N. Makhova

  DOI：10.1016/j.tet.2015.07.034

  日期：2015.9

  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.
• Nitro-, Cyano-, and Methylfuroxans, and Their Bis-Derivatives: From Green Primary to Melt-Cast Explosives
  作者：Alexander A. Larin、Dmitry M. Bystrov、Leonid L. Fershtat、Alexey A. Konnov、Nina N. Makhova、Konstantin A. Monogarov、Dmitry B. Meerov、Igor N. Melnikov、Alla N. Pivkina、Vitaly G. Kiselev、Nikita V. Muravyev

  DOI：10.3390/molecules25245836

  日期：——

  4′-azobis-dicarbamoyl furoxan is proposed as a substitute of pentaerythritol tetranitrate, a benchmark brisant high explosive. Finally, the application prospects of 3,3′-azobis-dinitro furoxan, one of the most powerful energetic materials synthesized up to date, are limited due to the tremendously high mechanical sensitivity of this compound. Overall, the investigated derivatives of furoxan comprise multipurpose

  在目前的工作中，我们详细研究了 1,2,5-恶二唑-2-氧化物（呋喃）的 20 种硝基、氰基和甲基衍生物的热化学、热稳定性、机械敏感性和爆轰性能。他们的二元衍生物。对于所有研究的物种，我们还使用高度准确的多级程序 W2-F12 和/或 W1-F12 结合原子化能量方法和等线反应确定了气相形成焓的可靠值。耦合簇技术的轨道 (DLPNO) 修改。除此之外，我们还提出了呋喃烷及其许多（偶氮）双衍生物的形成焓的可靠基准值。此外，我们还报告了以前未知的 3-cyano-4-nitrofuroxan 的晶体结构。在单环化合物中，呋喃的 3-硝基-4-环丙基和二氰基衍生物优于基准熔铸炸药三硝基甲苯，表现出良好的热稳定性（分解温度 >200°C）和对机械刺激不敏感，同时具有显着的挥发性和低熔点。反过来，4,4'-偶氮双-二氨基甲酰基呋喃烷被提议作为四硝酸季戊四醇酯的替代品，这是一种基准的强炸药。最后，3,