4,6-dinitrobenzo[c]isoxazole | 29245-51-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 4,6-dinitrobenzo[c]isoxazole
• 英文别名: 4,6-dinitroanthranil；4,6-dinitro-benzo[c]isoxazole；4,6-dinitro-benz[c]isoxazole；4,6-Dinitro-benz[c]isoxazol；4,6-Dinitro-anthranil；4,6-Dinitro-2,1-benzoxazole
• CAS: 29245-51-0
• 化学式: C₇H₃N₃O₅
• 分子量: 209.118
• InChiKey: SNGQABUPINYZFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 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：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,6-dinitrobenzo[c]isoxazole 在 一水合肼 作用下， 以 乙醇 为溶剂， 以75%的产率得到
  参考文献：
  名称：

  Superelectrophilic nature of 4,6-dinitrobenzo[c]isoxazole (4,6-dinitroanthranil) in [4+2]-cycloaddition reactions and σH-complex formation

  摘要：

  4,6-Dinitrobenzo[c]isoxazole (4,6-dinitroanthranil) acts as a dienophile and heterodiene in [4+2]-cycloaddition reactions, and its behaviour in sigma(H)-complex formation reactions has been examined.

  DOI：

  10.1016/j.mencom.2010.05.014
• 作为产物：
  描述：

  2,4,6-三硝基苯甲醛 在 sodium azide 、 三乙胺盐酸盐 作用下， 以 苯 、 甲苯 为溶剂， 反应 15.0h， 生成 4,6-dinitrobenzo[c]isoxazole
  参考文献：
  名称：

  4,6-二硝基邻氨基苯甲酸的制备合成

  摘要：

  建立了2-叠氮基-4,6-二硝基苯甲醛分子内环化合成4,6-二硝基邻氨基苯甲酸的制备方法。

  DOI：

  10.1007/s11172-010-0036-0

文献信息

• Double 1,3-dipolar cycloaddition of N-methyl Azomethine ylide to meta-Dinitrobenzene annelated with nitrogen aromatic heterocycles
  作者：Maxim A. Bastrakov、Alexey M. Starosotnikov、Sergey Yu. Pechenkin、Vadim V. Kachala、Ivan V. Glukhov、Svyatoslav A. Shevelev

  DOI：10.1002/jhet.423

  日期：——

  The 1,3-dipolar cycloaddition of unstabilized azomethine ylide 1 with meta-dinitrobenzene fused with nitrogen heterocycles affords the corresponding decahydropyrrolo[3,4-e]isoindole cycloadducts in good yields. This is a first example of [3+2]-cycloaddition of azomethine ylides to nitroarenes. J. Heterocyclic Chem., (2010).

  未稳定的甲亚胺基内酯1与间二硝基苯与氮杂环稠合的1,3-偶极环加成反应可提供相应的十氢吡咯并[3,4- e ]异吲哚环加合物，收率很高。这是将甲亚胺烷基化物[3 + 2]-环加成成硝基芳烃的第一个例子。J.杂环化​​学。（2010）。
• Reactions of 4,6-dinitrobenzo[c]isoxazoles with nucleophiles
  作者：V. V. Mezhnev、M. D. Dutov、V. V. Kachala、S. A. Shevelev

  DOI：10.1007/s11172-010-0128-x

  日期：2010.3

  Reactions of nucleophiles with 3-R-4, 6-dinitrobenzo[c]isoxazoles (anthranils) were studied. Reactions of 4, 6-dinitroanthranil (R = H) with anionic O- and S-nucleophiles (phenols and benzenethiols in the presence of K2CO3) do not result in displacement of the nitro groups. The malonodinitrile anion (C-nucleophile) attacks the C(3) atom with opening of the isoxazole ring followed by recyclization into 2-amino-5,7-dinitroquinoline-3-carbonitrile N-oxide. The 5-NO2 group in the latter is smoothly replaced under the action of benzenethiol and 4-chlo-rophenol in the presence of K2CO3. In the case of 3-substituted anthranil (R = COCH3), one nitro group (4-NO2) is replaced under the action of benzenethiol and NaN3.

  研究了亲核物与 3-R-4，6-二硝基苯并[c]异恶唑（anthranils）的反应。4，6-二硝基蒽醌（R = H）与阴离子 O 型和 S 型亲核物（在 K2CO3 存在下的苯酚和苯硫酚）的反应不会导致硝基位移。丙二腈阴离子（C-亲核物）攻击 C（3）原子，打开异噁唑环，然后再生成 2-氨基-5,7-二硝基喹啉-3-甲腈 N-氧化物。在 K2CO3 的作用下，后者中的 5-NO2 基团在苯硫酚和 4-chlo-rophenol 的作用下被顺利取代。在 3-取代的蒽醌（R = COCH3）中，一个硝基（4-NO2）在苯硫酚和 NaN3 的作用下被取代。
• Thermal Stability Studies on a Homologous Series of Nitroarenes
  作者：Jimmie C. Oxley、James L. Smith、Hong Ye、Robert L. McKenney、Paul R. Bolduc

  DOI：10.1021/j100023a043

  日期：1995.6

  The thermal stabilities of a number of nitroarenes were examined in solution and in condensed phase. In general, increasing the number of nitro groups decreased thermal stability. Changing the substituent on 1-X-2,4,6-trinitrobenzene from X = H to NH2 to CH3 to OH accelerated decomposition; this effect was attributed to increased ease of intramolecular proton transfer to an ortho nitro group, thus weakening the carbon-nitrogen bond. In solution, the effect of increasing substitution from n = 1 to n = 3 on X(n)(NO2)(3)C6H3-n was uniformly that of decreasing the thermal stability of the species. However, in condensed phase, results suggested that crystal habit may be more important than molecular structure; for X = Br, CH3, and NH2, the more substituted species was the more stable.
• THE PHOTOCHEMICAL BEHAVIOR OF SOME o-NITROSTILBENES
  作者：JANET S. SPLITTER、MELVIN CALVIN

  DOI：10.1021/jo01365a019

  日期：1955.8
• Preparative synthesis of 4,6-dinitroanthranil
  作者：V. V. Mezhnev、M. D. Dutov、S. A. Shevelev

  DOI：10.1007/s11172-010-0036-0

  日期：2009.2

  A preparative method for the synthesis of 4,6-dinitroanthranil by intramolecular cyclization of 2-azido-4,6-dinitrobenzaldehyde was developed.

  建立了2-叠氮基-4,6-二硝基苯甲醛分子内环化合成4,6-二硝基邻氨基苯甲酸的制备方法。