3,3-Bis(3,6-dihydroxynaphthalen-2-yl)-2-benzofuran-1-one | 1368254-72-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,3-Bis(3,6-dihydroxynaphthalen-2-yl)-2-benzofuran-1-one
• 英文别名: 3,3-bis(3,6-dihydroxynaphthalen-2-yl)-2-benzofuran-1-one
• CAS: 1368254-72-1
• 化学式: C₂₈H₁₈O₆
• 分子量: 450.447
• InChiKey: WOJZEQITMNPSHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,3-Bis(3,6-dihydroxynaphthalen-2-yl)-2-benzofuran-1-one 在 甲烷磺酸 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以77%的产率得到7',19'-Dihydroxyspiro[2-benzofuran-3,13'-2-oxapentacyclo[12.8.0.03,12.05,10.016,21]docosa-1(14),3(12),4,6,8,10,15,17,19,21-decaene]-1-one
  参考文献：
  名称：

  Exhaustive Syntheses of Naphthofluoresceins and Their Functions

  摘要：

  Naphthofluorescein and/or seminaphthofluorescein derivatives possessing the additional benzene units to one or both sides of fluorescein were exhaustively constructed through Friedel-Crafts type reactions between corresponding aroylbenzoic acids and dihydroxynaphthalenes. Compound 4 works as a one-dye pH indicator, which shows red in strong acid condition and blue in basic solution. Compound 23 (diacetate of compound 4) shows good transitivity to the HEK 293 cells and acts as a fluorescent pigment for the living cell imaging. Compounds 5, 6, and 9 show fluorescent emission in the NIR region (>700 nm) and imply the potentialities of NIR fluorescent probes.

  DOI：

  10.1021/jo300177b
• 作为产物：
  描述：

  3-bromonaphthalene-2,7-diol 在 盐酸 、 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 13.0h， 生成 3,3-Bis(3,6-dihydroxynaphthalen-2-yl)-2-benzofuran-1-one
  参考文献：
  名称：

  Exhaustive Syntheses of Naphthofluoresceins and Their Functions

  摘要：

  Naphthofluorescein and/or seminaphthofluorescein derivatives possessing the additional benzene units to one or both sides of fluorescein were exhaustively constructed through Friedel-Crafts type reactions between corresponding aroylbenzoic acids and dihydroxynaphthalenes. Compound 4 works as a one-dye pH indicator, which shows red in strong acid condition and blue in basic solution. Compound 23 (diacetate of compound 4) shows good transitivity to the HEK 293 cells and acts as a fluorescent pigment for the living cell imaging. Compounds 5, 6, and 9 show fluorescent emission in the NIR region (>700 nm) and imply the potentialities of NIR fluorescent probes.

  DOI：

  10.1021/jo300177b