3,3',4,4'-tetramethoxyazoxybenzene | 87587-65-3

• 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
• 英文别名: bis-(3,4-dimethoxy-phenyl)-diazene-N-oxide；Bis-(3,4-dimethoxy-phenyl)-diazen-N-oxid；3.4.3'.4'-Tetramethoxy-azoxybenzol；4.4'-Azoxyveratrol；4-[(Z)-(3,4-Dimethoxyphenyl)-NNO-azoxy]-1,2-dimethoxybenzene；(3,4-dimethoxyphenyl)-(3,4-dimethoxyphenyl)imino-oxidoazanium
• CAS: 87587-65-3
• 化学式: C₁₆H₁₈N₂O₅
• 分子量: 318.329
• InChiKey: KVUSGSCXFPUODX-UHFFFAOYSA-N

物化性质

• 熔点：
  172-182 °C
• 沸点：
  475.0±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,3',4,4'-tetramethoxyazoxybenzene 在 铁粉 作用下， 生成 1,2-bis(3,4-dimethoxyphenyl)diazene
  参考文献：
  名称：

  Robinson, Journal of the Chemical Society, 1917, vol. 111, p. 117

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-二甲氧基-4-硝基苯 在 甲醇 、 sodium methylate 作用下， 生成 3,3',4,4'-tetramethoxyazoxybenzene
  参考文献：
  名称：

  Robinson, Journal of the Chemical Society, 1917, vol. 111, p. 117

  摘要：

  DOI：

文献信息

• Photosubstitution-photoreduction mechanistic duality in the SET photoreactions of nitrophenyl ethers with amines. The role of the steps that follow the ET
  作者：Miquel Mir、Jordi Marquet、Oriol Massot

  DOI：10.1016/s0040-4020(99)00735-8

  日期：1999.10

  photoreduced by primary amines in water through a mechanism initiated by single electron transfer that is in direct competition with the single electron transfer photosubstitution mechanism (SNAr∗-SET). Our results indicate that the preferred pathway does not depend on the electron donor or proton donor ability of the amine. The key factor that determines the progress of the photoreaction is the structure

  硝基苯醚通过在水中的伯胺通过单电子转移，其与单电子转移机理photosubstitution直接竞争（S发起的机制光还原Ñ氩* -SET）。我们的结果表明，优选的途径不取决于胺的电子给体或质子给体能力。决定光反应进展的关键因素是胺的碳骨架的结构，特别是碳原子上与氨基相连的氢的类型。讨论了以氢原子转移为关键步骤的机械原理。
• Solid state photochemistry of ternary cyclodextrin complexes: Total selectivity in the photoreduction of nitrophenyl ethers by 1-phenylethylamine
  作者：Miquel Mir、Jorge Marquet、Eduard Cayón

  DOI：10.1016/s0040-4039(00)60931-0

  日期：1992.11

  The irradiation of the ternary complexes of beta-cyclodextrin with several nitrophenyl ethers, and 1-phenylethylamine in the solid state, produces selective photoreduction to the corresponding nitroso derivatives.
• Effect of Topologically Controlled Coulombic Interactions on the Dynamic Behavior of Photoexcited Nitrophenyl Alkyl Ethers in the Presence of Tertiary Amines with Limited Motion Freedom
  作者：Roberto Gonzalez-Blanco、José L. Bourdelande、Jordi Marquet

  DOI：10.1021/jo961821i

  日期：1997.10.1

  Time-resolved electronic absorption spectroscopy has been successfully applied to clarify the mechanism of the ''abnormal'' photochemical cleavage of 4-nitrophenyl piperidinoalkyl ethers induced by controlled Coulombic disturbance of the ''normal'' electronic distribution of the radical anion intermediate. Thus, photolysis of 1-piperidino-2-(2-methoxy-4-nitrophenoxy (a system with an amine with limited freedom of motion) in acetonitrile leads to C-O bond photocleavage in a relatively slow process (k approximate to 4 x 10(5) s(-1)) from intermediate species that show radical-ion pair behavior. Systems with higher freedom of motion of the amine moiety, such as 1-piperidino-5-(2-methoxy-4-nitrophenoxy)pentane or 4-nitroveratrole + triethylamine, show the intermediate radical-ion pairs mainly evolving to reduction products, probably a result of intermediates with geometries not allowed for the system with limited freedom of motion of the amine.
• Approaches to azepines: a new azepine by the photolysis of dimethyl p-azidosalicylate
  作者：Reginald A. Mustill、Alun H. Rees

  DOI：10.1021/jo00173a048

  日期：1983.12