4,6-dinitro-7-methylbenzofuroxan | 19262-17-0

• 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: 4,6-dinitro-7-methylbenzofuroxan
• 英文别名: 4-Methyl-5,7-dinitro-3-oxido-2,1,3-benzoxadiazol-3-ium
• CAS: 19262-17-0
• 化学式: C₇H₄N₄O₆
• 分子量: 240.132
• InChiKey: WVYAVCBXYYOGRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-Nitro-7-methyl-benzofuroxan 在 硫酸 、 硝酸 作用下， 生成 4,6-dinitro-7-methylbenzofuroxan
  参考文献：
  名称：

  潜在的抗白血病和免疫抑制药物。一些苯并-2,1,3-恶二唑（苯并呋喃）及其N-氧化物（苯并呋喃）的制备及其体外药理活性。

  摘要：

  DOI：

  10.1021/jm00308a027

文献信息

• 4,6-Dinitro-7-methylbenzofuroxan: a strong carbon acid of very low intrinsic reactivity
  作者：Francois Terrier、Denis Croisat、Alain Pierre Chatrousse、Marie Jose Pouet、Jean Claude Halle、Guy Jacob

  DOI：10.1021/jo00039a032

  日期：1992.6

  Rates of ionization of 4,6-dinitro-7-methylbenzofuroxan (3) by water, hydroxide ion, and various general bases have been measured in aqueous solution at t = 25-degrees-C. The solvent pathway is the major process contributing to the formation of the resulting carbanion (C-3) in solutions of pH less-than-or-equal-to 8. The very high thermodynamic stability of C-3 (pK(a)CH = 2.50), the exocyclic carbon of which is essentially olefinic in nature, is shown to derive for the most part from an extensive delocalization of the negative charge through the two nitro groups and the annelated furoxan ring. In agreement with the idea that considerable molecular, electronic, and solvational reorganization is required to produce a highly delocalized carbanion, the deprotonation of 3 is associated with one of the highest intrinsic energy barriers for proton transfer so far measured in aqueous solution (DELTA-G0(double dagger) = 85.5 kJ mol-1). The strong acidity of 3 also emphasizes the exceptional activating effect of a 4,6-dinitrobenzofuroxan moiety.