dioctyl 2,6-dimethylbenzo[1,2-b:4,5-b']difuran-3,7-dicarboxylate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dioctyl 2,6-dimethylbenzo[1,2-b:4,5-b']difuran-3,7-dicarboxylate
• 英文别名: Dioctyl 2,6-dimethylfuro[2,3-f][1]benzofuran-3,7-dicarboxylate；dioctyl 2,6-dimethylfuro[2,3-f][1]benzofuran-3,7-dicarboxylate
• 化学式: C₃₀H₄₂O₆
• 分子量: 498.66
• InChiKey: BUUKOGVOXWQHJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  36
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dioctyl 2,6-dimethylbenzo[1,2-b:4,5-b']difuran-3,7-dicarboxylate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 24.0h， 以58%的产率得到dioctyl 2,6-bis(bromomethyl)benzo[1,2-b:4,5-b']difuran-3,7-dicarboxylate
  参考文献：
  名称：

  Synthesis and photoluminescent properties of conjugated aryl–vinyl dioctyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7-dicarboxylate derivatives

  摘要：

  The synthesis of highly fluorescent conjugated benzodifuran aryl vinyl systems, containing four double bonds and at least four phenyl rings, is described. The ethyl groups of diethyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7-dicarboxylate, obtained by the Michael type condensation of p-benzoquinone and ethyl acetoacetate, were replaced by octyl groups via the transesterification reaction to improve the desired product solubility in common organic solvents. The dioctyl ester was brominated and Used for the Wittig reaction with stilbene aldehydes, obtained by the Heck reaction of 4-bromobenzaldehyde and an appropriate styrene. The products, obtained in 48-92% yield, exhibit the UV-Vis fluorescence with high quantum yields, 58-69%. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.07.006
• 作为产物：
  描述：

  辛醇 、 diethyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7-dicarboxylate 在 potassium phosphate 、 叔丁胺氢溴酸盐 作用下， 反应 9.0h， 以78%的产率得到dioctyl 2,6-dimethylbenzo[1,2-b:4,5-b']difuran-3,7-dicarboxylate
  参考文献：
  名称：

  Synthesis and photoluminescent properties of conjugated aryl–vinyl dioctyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7-dicarboxylate derivatives

  摘要：

  The synthesis of highly fluorescent conjugated benzodifuran aryl vinyl systems, containing four double bonds and at least four phenyl rings, is described. The ethyl groups of diethyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7-dicarboxylate, obtained by the Michael type condensation of p-benzoquinone and ethyl acetoacetate, were replaced by octyl groups via the transesterification reaction to improve the desired product solubility in common organic solvents. The dioctyl ester was brominated and Used for the Wittig reaction with stilbene aldehydes, obtained by the Heck reaction of 4-bromobenzaldehyde and an appropriate styrene. The products, obtained in 48-92% yield, exhibit the UV-Vis fluorescence with high quantum yields, 58-69%. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.07.006

文献信息

• Synthesis and photoluminescent properties of conjugated aryl–vinyl dioctyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7-dicarboxylate derivatives
  作者：Mariusz J. Bosiak、Marcin Rakowiecki、Katarzyna J. Orłowska、Dariusz Kędziera、Jörg Adams

  DOI：10.1016/j.dyepig.2013.07.006

  日期：2013.12

  The synthesis of highly fluorescent conjugated benzodifuran aryl vinyl systems, containing four double bonds and at least four phenyl rings, is described. The ethyl groups of diethyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7-dicarboxylate, obtained by the Michael type condensation of p-benzoquinone and ethyl acetoacetate, were replaced by octyl groups via the transesterification reaction to improve the desired product solubility in common organic solvents. The dioctyl ester was brominated and Used for the Wittig reaction with stilbene aldehydes, obtained by the Heck reaction of 4-bromobenzaldehyde and an appropriate styrene. The products, obtained in 48-92% yield, exhibit the UV-Vis fluorescence with high quantum yields, 58-69%. (C) 2013 Elsevier Ltd. All rights reserved.