5-(benzo[d]oxazol-2-yl)-3-iodo-2-(4-methoxyphenyl)benzofuran-6-ol | 1618110-50-1

• 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-iodo-2-(4-methoxyphenyl)benzofuran-6-ol
• CAS: 1618110-50-1
• 化学式: C₂₂H₁₄INO₄
• 分子量: 483.262
• InChiKey: MNDDURXSFBBARP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.23
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  68.63
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(benzo[d]oxazol-2-yl)-3-iodo-2-(4-methoxyphenyl)benzofuran-6-ol 、 (4-di-n-butylamino)phenylacetylene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 甲苯 为溶剂， 以43%的产率得到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
• 作为产物：
  描述：

  在 吡啶 、 碘 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 5-(benzo[d]oxazol-2-yl)-3-iodo-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