5-(benzo[d]oxazol-2-yl)-3-((4-(dibutylamino)phenyl)ethynyl)-2-(4-methoxyphenyl)benzofuran-6-ol | 1618110-54-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 5-(benzo[d]oxazol-2-yl)-3-((4-(dibutylamino)phenyl)ethynyl)-2-(4-methoxyphenyl)benzofuran-6-ol
• CAS: 1618110-54-5
• 化学式: C₃₈H₃₆N₂O₄
• 分子量: 584.715
• InChiKey: RXLBSFWVWSDJJL-UHFFFAOYSA-N

物化性质

• 沸点：
  657.4±55.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.43
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  71.87
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  三氟化硼乙醚 、 5-(benzo[d]oxazol-2-yl)-3-((4-(dibutylamino)phenyl)ethynyl)-2-(4-methoxyphenyl)benzofuran-6-ol 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 以79%的产率得到1-((4-(dibutylamino)phenyl)ethynyl)-6,6-difluoro-2-(4-methoxyphenyl)-6H-6l4-benzo[4,5]oxazolo[3,2-c]benzofuro[5,6-e][1,3,2]oxazaborinin-7-ium
  参考文献：
  名称：

  Fluorescent 2-(2′-hydroxybenzofuran)benzoxazole (HBBO) borate complexes: synthesis, optical properties, and theoretical calculations

  摘要：

  The multi-step synthesis, structural and optical properties of original luminescent borate complexes derived from 2-(2 '-hydroxybenzofuran)benzoxazole (HBBO) are reported. Functionalization at position 3 of the benzofuran ring was readily achieved through an electrophilic cyclization key step followed by a Sonogashira cross-coupling reaction. The optical properties of the resulting boron difluoride dyes highlight different photophysical behaviors depending on the nature of the substitution at position 3 of the benzofuran core (Bu-t-phenylacetylene or (NBu2)-Bu-n-phenylacetylene). The (NBu2)-Bu-n-phenylacetylene moiety favors a sizeable intramolecular charge transfer as evidenced by a strong solvatochromism; a feature further confirmed by ab initio calculations. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.002
• 作为产物：
  描述：

  在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碘 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 5-(benzo[d]oxazol-2-yl)-3-((4-(dibutylamino)phenyl)ethynyl)-2-(4-methoxyphenyl)benzofuran-6-ol
  参考文献：
  名称：

  Fluorescent 2-(2′-hydroxybenzofuran)benzoxazole (HBBO) borate complexes: synthesis, optical properties, and theoretical calculations

  摘要：

  The multi-step synthesis, structural and optical properties of original luminescent borate complexes derived from 2-(2 '-hydroxybenzofuran)benzoxazole (HBBO) are reported. Functionalization at position 3 of the benzofuran ring was readily achieved through an electrophilic cyclization key step followed by a Sonogashira cross-coupling reaction. The optical properties of the resulting boron difluoride dyes highlight different photophysical behaviors depending on the nature of the substitution at position 3 of the benzofuran core (Bu-t-phenylacetylene or (NBu2)-Bu-n-phenylacetylene). The (NBu2)-Bu-n-phenylacetylene moiety favors a sizeable intramolecular charge transfer as evidenced by a strong solvatochromism; a feature further confirmed by ab initio calculations. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.002