3-acetyl-4-aminofuroxan

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetyl-4-aminofuroxan
• 英文别名: 4-amino-3-acetylfuroxan；3-Acetyl-4-amino-1,2,5-oxadiazole 2-oxide；1-(4-amino-2-oxido-1,2,5-oxadiazol-2-ium-3-yl)ethanone
• 化学式: C₄H₅N₃O₃
• 分子量: 143.102
• InChiKey: YGWVNYBUYBFDCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  94.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-acetyl-4-aminofuroxan 在 盐酸 、 溴 作用下， 反应 24.0h， 以97%的产率得到4-amino-3-(α-bromoacetyl)furoxan
  参考文献：
  名称：

  呋喃和呋喃的溴乙酰衍生物与S-亲核试剂的反应

  摘要：

  Hetarylthioacetyl- 和 (2-aminothiazol-4-yl) furoxans 和相应的以前未知的呋喃类化合物分别通过取代的溴乙酰基呋喃类化合物和呋喃类化合物与杂芳基硫醇和硫脲的反应合成。

  DOI：

  10.1007/bf02495521

文献信息

• Dinitrofuroxan cycloreversion as a novel general approach for the synthesis of nitroazoles
  作者：L. L. Fershtat、D. V. Khakimov、N. N. Makhova

  DOI：10.1007/s11172-015-0878-6

  日期：2015.2

  A novel general approach towards various nitroazoles via tandem process involving dinitrofuroxan cycloreversion followed by [3+2] cycloaddition of generated in situ nitroformonitrile oxide is developed. The reaction is promoted by addition of catalytic amounts of ionic liquids. Plausible mechanisms of the described processes based on quantum chemical calculations are proposed.

  开发了一种通过涉及二硝基呋咱环反转后跟生成的当场硝基亚甲硝基氧化物的[3+2]环加成串联过程来合成各种硝基唑类的新型通用方法。反应通过加入催化量的离子液体来促进。基于量子化学计算，提出了所描述过程的可能机制。
• Reduction of the furoxan ring to the furazan ring in some carbonyl-substituted furoxans
  作者：A. S. Kulikov、N. N. Makhova、T. I. Godovikova、S. P. Golova、L. I. Khmel'nitskii

  DOI：10.1007/bf00699838

  日期：1994.4

  It was shown that the furoxan ring is efficiently reduced to the furazan ring in carbonylsubstituted furoxans with other functional groups by the action of the SnCl2-HC1-AcOH system.

  结果表明，在 SnCl2-HCl-AcOH 体系的作用下，呋喃环在具有其他官能团的羰基取代呋喃中有效还原为呋喃环。
• Synthesis and nitration of 3-R-4-(2,2,2-trinitroethyl)aminofuroxans
  作者：M. A. Epishina、A. O. Finogenov、A. S. Kulikov、N. N. Makhova、I. V. Anan’ev、V. A. Tartakovsky

  DOI：10.1007/s11172-012-0209-0

  日期：2012.8

  Simple methods for the synthesis of 3-R-4-(2,2,2-trinitroethyl)aminofuroxans were developed based on the Mannich reaction of N,N′-bis(3-R-furoxan-4-yl)methylenediamines with trinitromethane or 3-R-4-aminofuroxans with trinitroethanol or with CH2O and trinitromethane. The Mannich bases obtained were studied in the nitration reaction, which showed their ability to form nitramines depending on substituents on the furoxan ring.

  开发了简单的方法来合成3-R-4-(2,2,2-三硝基乙基)氨基呋喃噁唑，基于N,N′-双(3-R-呋喃噁唑-4-基)亚甲基二胺与三硝基甲烷或3-R-4-氨基呋喃噁唑与三硝基乙醇或与甲醛和三硝基甲烷的曼尼希反应。对获得的曼尼希碱进行了研究，结果表明它们在硝化反应中形成硝胺的能力取决于呋喃噁唑环上的取代基。
• Thermally induced rearrangement of the arylhydrazones of furoxan-3-yl carbonyl compounds
  作者：Sergey I. Molotov、Margarita A. Epishina、Alexander S. Kulikov、Yulia V. Nelyubina、Konstantin A. Lyssenko、Kirill Yu. Suponitsky、Nina N. Makhova

  DOI：10.1070/mc2006v016n05abeh002359

  日期：2006.1

  A thermally induced rearrangement of arylhydrazones 5 of furoxan-3-yl carbonyl compounds into 2-aryl-5-(hydroximino)(aryl)- methyl-2H-1,2,3-triazole 1-oxides 6 has been found for the first time; the crystal packing of compound 6a has been studied by X-ray diffraction analysis.

  首次发现将呋喃喃-3-基羰基化合物的芳基hydr5热诱导重排为2-芳基-5-（氢氧氨基）（芳基）-甲基-2H-1,2,3-三唑1-氧化物6时间; 通过X射线衍射分析研究了化合物6a的晶体堆积。
• Lewis acid-catalyzed Wolff cyclocondensation in the synthesis of (1H-1,2,3-triazolyl)furoxans
  作者：Leonid L. Fershtat、Maxim R. Radzhabov、Anna A. Romanova、Ivan V. Ananyev、Nina N. Makhova

  DOI：10.24820/ark.5550190.p010.070

  日期：——

  Novel regioselective approach to the synthesis of (1H-1,2,3-triazol-1-yl)furoxans based on Lewis acid-catalyzed Wolff cyclocondensation of aminofuroxans with diazo-β-dicarbonyl compounds has been developed. This approach allows to involve aminofuroxans as substrates which are very weak nucleophiles and usually do not participate in reactions with common electrophiles.

  基于路易斯酸催化的氨基呋喃与重氮-β-二羰基化合物的沃尔夫环缩合反应，已经开发了合成（1H-1,2,3-三唑-1-基）呋喃的新型区域选择性方法。这种方法允许将氨基呋喃作为底物，它们是非常弱的亲核试剂，通常不参与与普通亲电试剂的反应。