5-formyl-3-iodo-2-(4-methoxyphenyl)benzofuran-6-yl acetate | 1618110-49-8

• 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-formyl-3-iodo-2-(4-methoxyphenyl)benzofuran-6-yl acetate
• CAS: 1618110-49-8
• 化学式: C₁₈H₁₃IO₅
• 分子量: 436.203
• InChiKey: DKNCBUJXOUJPCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  65.74
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-formyl-3-iodo-2-(4-methoxyphenyl)benzofuran-6-yl acetate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 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 3.08h， 生成 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：

  2-羟基-4-甲氧基苯甲醛 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碘 、 一氯化碘 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 5-formyl-3-iodo-2-(4-methoxyphenyl)benzofuran-6-yl acetate
  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