5,7-dichloro-4,6-dinitrobenzofuroxan | 117907-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 5,7-dichloro-4,6-dinitrobenzofuroxan
• 英文别名: 4,6-dinitro-5,7-dichlorobenzofuroxan；5,7-dichloro-4,6-dinitrobenzofuroxane；2,1,3-Benzoxadiazole, 4,6-dichloro-5,7-dinitro-, 3-oxide；4,6-dichloro-5,7-dinitro-3-oxido-2,1,3-benzoxadiazol-3-ium
• CAS: 117907-71-8
• 化学式: C₆Cl₂N₄O₆
• 分子量: 294.995
• InChiKey: OMVXFMLRNAVEHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  482.0±55.0 °C(Predicted)
• 密度：
  2.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5,7-dichloro-4,6-dinitrobenzofuroxan 、 两性霉素B 以 二甲基亚砜 为溶剂， 反应 2.0h， 以68%的产率得到19E,21E,25E,27E,29E,31E-5,7-bis({2-[(36-carboxy-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-33-yl)oxy]-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-4-yl}amino)-4,6-dinitrobenzo[c][1,2,5]oxadiazole-1-oxide
  参考文献：
  名称：

  Synthesis and biological activity of new hybrids compounds derived from benzofuroxanes and polyene antibiotics

  摘要：

  Hybrid compounds based on 4,6-dichloro-5-nitrobenzofuroxan, 7-chloro-4,6-dinitrobenzofuroxan, 5,7-dichloro-4,6-dinitrobenzofuroxan, and polyene antibiotics (amphotericin B and nystatin) have been prepared for the first time. They have exhibited biological activity comparable to that of starting antibiotics. Activity of the compound derived from 5,7-dichloro-4,6-dinitrobenzofuroxan and nystatin towards Trichophyton mentagrophytes is 4 times higher than that of nystatin.

  DOI：

  10.1134/s1070363216050091
• 作为产物：
  描述：

  4,6-Dichlor-benzofuroxan 、 硝酸 生成 5,7-dichloro-4,6-dinitrobenzofuroxan
  参考文献：
  名称：

  CHAFIN, ANDREW P.;ATKINS, RONALD L.

  摘要：

  DOI：

文献信息

• Synthesis, structure, and biologic activity of products of reactions between dinitrodichlorobenzofuroxane and aminopyrimidines in aqueous dimethyl sulfoxide
  作者：I. V. Galkina、L. M. Yusupova、A. T. Gubaidullin、V. I. Galkin

  DOI：10.1134/s1070428016050201

  日期：2016.5

  Reactions of 4,6-dinitro-5,7-dichlorobenzofuroxane with substituted pyrimidines in aqueous DMSO proceed through an intermediate formation of 5-hydroxy-4,6-dinitro-7-chlorobenzofuroxane owing to the hydrolysis of one of the chlorine atoms with the subsequent formation of pyrimidine salts exhibiting a high biologic action.

  在4DMSO水溶液中，4,6-二硝基-5,7-二氯苯并呋喃烷与取代的嘧啶的反应通过5-羟基-4,6-二硝基-7-氯苯并呋喃的中间体形成而进行，这是由于其中一个氯原子水解而形成的。随后形成的嘧啶盐具有较高的生物活性。
• Synthesis and investigation of antimicrobial activity of compounds derived from benzo[C][1,2,5]oxadiazole-1-oxides and phenolates
  作者：Elena A. Chugunova、Nurgali I. Akylbekov、Alexandra D. Voloshina、Natalia V. Kulik、Vladimir V. Zobov、Vasily M. Babaev、Nikolai V. Gavrilov、Alexander R. Burilov

  DOI：10.1080/00397911.2016.1213295

  日期：2016.9.16

  product, we observed the hydrolysis of the second chlorine and replacement of it by hydroxyl group. Products of reaction of 4,6-dichloro-5-nitrobenzofuroxan with phenolates display excellent antimicrobial activity and have dual action, both against bacteria and fungi. GRAPHICAL ABSTRACT

  摘要 (二) 氯(二) 硝基苯并呋喃在异丙醇介质中与酚盐形成涉及碳原子的取代产物。在4,6-二硝基-5,7-二氯苯并呋喃的情况下，除了替换一个氯原子并形成C键产物外，我们还观察到第二个氯的水解和羟基的替换。4,6-二氯-5-硝基苯并呋喃与酚盐的反应产物显示出优异的抗菌活性，并具有双重作用，可对抗细菌和真菌。图形概要
• Synthesis, Structure, and Antimicrobial Activity of the Reaction Products of Chloronitro-Substituted Benzofurazanes and Benzofuroxanes with Morpholine
  作者：I. V. Galkina、G. L. Takhautdinova、K. A. Ivshin、L. M. Yusupova、I. I. Krasnyuk、S. N. Egorova、M. P. Shulaeva、O. K. Pozdeev、O. N. Kataeva、V. I. Galkin

  DOI：10.1134/s107036321712009x

  日期：2017.12

  amination reactions of morpholine with a series of chloronitro-substituted benzofurazanes and -furoxanes were studied. The reactions of morpholine with 5,7-dichloro-4,6-dinitrobenzofuroxane and 4-chloro-5-nitro- and 5-chloro-4-nitrobenzofurazanes gave products of the aromatic nucleophilic substitution of the chlorine substituents in the nitrogenous heterocycles. The composition and structure of the products

  研究了吗啉与一系列氯硝基取代的苯并呋喃烷和-呋喃烷的新胺化反应。吗啉与5,7-二氯-4,6-二硝基苯并呋喃烷和4-氯-5-硝基-和5-氯-4-硝基苯并呋喃氮烷的反应产生了含氮杂环中氯取代基的芳族亲核取代产物。产品的组成和结构是通过化学，物理和物理化学方法确定的。吗啉与4,6-二硝基苯并呋喃的反应生成了稳定的Meisenheimerσ-络合物，其结构通过X射线衍射分析进行了评估。合成的化合物对病原性人和动物菌群具有很高的抗菌和抗真菌活性。
• An Unusual Reaction of Triphenylphosphine with Dichlorodinitrobenzofuroxan
  作者：Irina V. Galkina、Elena V. Tudriy、Olga N. Kataeva、Luiza M. Yusupova、Heinrich Luftmann、Vladimir I. Galkin

  DOI：10.1080/10426500902719636

  日期：2009.4.7

  A novel phosphorylation reaction of dichlorodinitrobenzofuroxan by triphenylphosphine has been studied. An unusual course of the reaction with the participation of benzofuroxan nitro groups as reactive centers has been established. It is shown that as final product of the reaction, a stable diphenolate diphosphabetaine with strong participation of the mesomeric ketoylide structure is formed. The structure

  研究了三苯基膦对二氯二硝基苯并呋喃的新型磷酸化反应。已经建立了一个不寻常的反应过程，其中苯并呋喃硝基作为反应中心参与其中。结果表明，作为反应的最终产物，形成了稳定的二酚二磷酸甜菜碱，其中强烈参与了内消旋酮酰化物结构。X射线衍射证实了产物的结构。
• Synthesis and biological evaluation of novel structural hybrids of benzofuroxan derivatives and fluoroquinolones
  作者：Elena Chugunova、Nurgali Akylbekov、Adelya Bulatova、Nikolai Gavrilov、Alexandra Voloshina、Natalia Kulik、Vladimir Zobov、Alexey Dobrynin、Victor Syakaev、Alexander Burilov

  DOI：10.1016/j.ejmech.2016.03.086

  日期：2016.6

  A series of novel hybrids based on benzofuroxan derivatives and fluoroquinolones (4a-d-6a-d) have been synthesized. Unexpectedly, the reactions have resulted in salt products formation during the hydrolysis of benzofuroxans by water molecules being present in the solvent instead of usual substitution products. All the compounds have been screened for antimicrobial and toxic activities. All resulting compounds retain high activity characteristic for fluoroquinolones. Many of the salts based on benzofuroxans and fluoroquinolones have higher activity than starting fluoroquinolones against Bacillus cereus 8035. Among the screened compounds, the compound 4d has shown the best antibacterial activity against B. cereus 8035, 8 times higher than the original Lomefloxacin (MBC value 1.5 mu g/mL). (C) 2016 Elsevier Masson SAS. All rights reserved.