5,6-dimethoxy-2,1,3-benzoxadiazole | 111611-40-6

• 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: 5,6-dimethoxy-2,1,3-benzoxadiazole
• CAS: 111611-40-6
• 化学式: C₈H₈N₂O₃
• 分子量: 180.163
• InChiKey: CTFSAZLZHDCYQP-UHFFFAOYSA-N

物化性质

• 熔点：
  178-181 °C
• 沸点：
  265.4±43.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-dimethoxy-2,1,3-benzoxadiazole 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 溴 、 溶剂黄146 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 72.33h， 生成 4,7-bis((4-(dodecyloxy)phenyl)ethynyl)-5,6-dimethoxy-2,1,3-benzoxadiazole
  参考文献：
  名称：

  2,1,3-Benzoxadiazole and 2,1,3-benzothiadiazole-based fluorescent compounds: Synthesis, characterization and photophysical/electrochemical properties

  摘要：

  Six new fluorescent compounds derived from 2,1,3-benzoxadiazole and 2,1,3-benzothiadiazole hetero-cycles with varying numbers of alkoxy chains were successfully synthesized. Sonogashira cross-coupling was used as the key synthetic step to link the central and terminal aromatic units through an acetylenic linker unit which ensures molecular planarity and extension of the conjugation. All of the synthesized compounds showed UV-vis absorption in the 426-437 nm range with reasonably high molar extinction coefficients. All six compounds emit in the green region of the visible spectrum with reasonably large Stokes shifts (95-107 nm) and medium emission efficiencies (phi(f) = 0.27-0.32). Electrochemical studies showed that the compounds have closely spaced HOMO and LUMO energy levels and that they may present good electron transporting properties. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.06.001
• 作为产物：
  描述：

  5,6-dimethoxybenzofuroxan 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以75%的产率得到5,6-dimethoxy-2,1,3-benzoxadiazole
  参考文献：
  名称：

  Takakis, Ioannis M.; Hadjimihalakis, Phaedon M.; Tsantali, Georgia G., Journal of Heterocyclic Chemistry, 1992, vol. 29, # 1, p. 123 - 128

  摘要：

  DOI：

文献信息

• The nucleophilic aromatic photosubstitutions of 4,5-dinitroveratrole with amines
  作者：Jorge Marquet、Marcial Moreno-Mañas、Adelina Vallribera、Albert Virgili、Joan Bertran、Angels Gonzalez-Lafont、Jose MXXX Lluch

  DOI：10.1016/s0040-4020(01)89963-4

  日期：1987.1

  4,5-Dinitroveratrole is effectively photosubstituted by amines with relatively high ionization potential such as methylamine, n-butylamine and ethyl glycinate, but is mainly photoreduced when amines with relatively low ionization potential, such as dimethyl or trimethylamine are used. The photoreduction of several aromatic dinitrocompounds by triethylamine gives nitroanilines. A mechanistic scheme

  4,5-二硝基维甲酸被具有较高电离势的胺（例如甲胺，正丁胺和甘氨酸乙酯）有效地光取代，但是当使用具有较低电离势的胺（例如二甲基或三甲胺）时，则主要被光还原。三乙胺将几种芳族二硝基化合物光还原，得到硝基苯胺。根据我们的实验结果以及基于MINDO / 3对基态和可能的中间体的计算，提出了一种包含我们的光致脱模和光还原的机制方案。
• Takakis Ioannis M., Hadjimihalakis Phaedon M., Tsantali Georgia G., Pilin+, J. Heterocycl. Chem., 29 (1992) N 1, S 123-128
  作者：Takakis Ioannis M., Hadjimihalakis Phaedon M., Tsantali Georgia G., Pilin+

  DOI：——

  日期：——
• MARQUET J.; MORENO-MANAS M.; VALLRIBERA A.; VIRGILI A.; BERTRAN J.; GONZA+, TETRAHEDRON, 43,(1987) N 2, 351-360
  作者：MARQUET J.、 MORENO-MANAS M.、 VALLRIBERA A.、 VIRGILI A.、 BERTRAN J.、 GONZA+

  DOI：——

  日期：——
• 2,1,3-Benzoxadiazole and 2,1,3-benzothiadiazole-based fluorescent compounds: Synthesis, characterization and photophysical/electrochemical properties
  作者：Behramand Behramand、Fernando Molin、Hugo Gallardo

  DOI：10.1016/j.dyepig.2012.06.001

  日期：2012.12

  Six new fluorescent compounds derived from 2,1,3-benzoxadiazole and 2,1,3-benzothiadiazole hetero-cycles with varying numbers of alkoxy chains were successfully synthesized. Sonogashira cross-coupling was used as the key synthetic step to link the central and terminal aromatic units through an acetylenic linker unit which ensures molecular planarity and extension of the conjugation. All of the synthesized compounds showed UV-vis absorption in the 426-437 nm range with reasonably high molar extinction coefficients. All six compounds emit in the green region of the visible spectrum with reasonably large Stokes shifts (95-107 nm) and medium emission efficiencies (phi(f) = 0.27-0.32). Electrochemical studies showed that the compounds have closely spaced HOMO and LUMO energy levels and that they may present good electron transporting properties. (C) 2012 Elsevier Ltd. All rights reserved.
• Takakis, Ioannis M.; Hadjimihalakis, Phaedon M.; Tsantali, Georgia G., Journal of Heterocyclic Chemistry, 1992, vol. 29, # 1, p. 123 - 128
  作者：Takakis, Ioannis M.、Hadjimihalakis, Phaedon M.、Tsantali, Georgia G.、Pilini, Helena

  DOI：——

  日期：——