3,3',4,4'-Tetramethoxyazoxybenzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,3',4,4'-Tetramethoxyazoxybenzene
• 化学式: C₁₆H₁₈N₂O₅
• 分子量: 318.329
• InChiKey: KVUSGSCXFPUODX-ZCXUNETKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.35
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1,2-二甲氧基-4-硝基苯 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以45%的产率得到3,3',4,4'-Tetramethoxyazoxybenzene
  参考文献：
  名称：

  通过双（三甲基甲硅烷基）酰胺钠进行硝基芳烃的新颖还原偶联中的1,2-消除，得到叠氮芳烃。

  摘要：

  [反应：请参见文字]。通过在150℃下于密封管中使用双（三甲基甲硅烷基）酰胺钠作为THF中的脱氧剂，成功地从2当量的相应硝基芳烃一步制备对称的叠氮芳烃。

  DOI：

  10.1021/ol050924x

文献信息

• Topologically Controlled Coulombic Interactions, a New Tool in the Developing of Novel Reactivity. Photochemical and Electrochemical Cleavage of Phenyl Alkyl Ethers
  作者：Jorge Marquet、Eduard Cayon、Xavier Martin、Francisco Casado、Iluminada Gallardo、Miquel Moreno、Jose M. Lluch

  DOI：10.1021/jo00117a037

  日期：1995.6

  The hypothesis that a specific placement of a positive charge would dramatically alter the behavior of a charged intermediate has been tested. Phenyl ethers substituted by electron-attracting groups do not undergo reductive fragmentation. However, related alpha-piperidino-omega-(4-substituted-phenoxy)-alkanes give alkyl ether photocleavage when the linker between the redox centers is short, or the usual substitution-reduction photochemistry when it is long. Mechanistic experiments suggest that the photofragmentation process operates through space intramolecular electron transfer to the triplet aromatic chromophore and that a coplanar relative orientation of the alkyl ether bond and the phenyl ring is compulsory for the photofragmentation to be observed. Configuration interaction AM1 calculations justify the described facts, indicating that the fragmentation process is only operative when a Coulombic stabilization of a sigma* intramolecular electron transfer excited state is produced. Electrochemical studies carried out with the corresponding quaternary salts (intermolecular generation of the phenyl ether radical anion) confirm the conclusions derived from the photochemical experiments.
• MUSTILL, R. A.;REES, A. H., J. ORG. CHEM., 1983, 48, N 25, 5041-5043
  作者：MUSTILL, R. A.、REES, A. H.

  DOI：——

  日期：——
• 1,2-Eliminations in a Novel Reductive Coupling of Nitroarenes to Give Azoxy Arenes by Sodium Bis(trimethylsilyl)amide
  作者：Jih Ru Hwu、Asish R. Das、Chia Wei Yang、Jiann-Jyh Huang、Ming-Hua Hsu

  DOI：10.1021/ol050924x

  日期：2005.7.1

  [reaction: see text]. Symmetric azoxy arenes were successfully prepared in one step from 2 equiv of the corresponding nitroarenes by use of sodium bis(trimethylsilyl)amide as the deoxygenating agents in THF at 150 degrees C in a sealed tube.

  [反应：请参见文字]。通过在150℃下于密封管中使用双（三甲基甲硅烷基）酰胺钠作为THF中的脱氧剂，成功地从2当量的相应硝基芳烃一步制备对称的叠氮芳烃。