2-<2,7-Dihydroxy-naphthoyl>-benzoesaeure | 25932-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-<2,7-Dihydroxy-naphthoyl>-benzoesaeure
• 英文别名: 2-(2,7-Dihydroxy-naphthoyl)-benzoesaeure；2-(2,7-Dihydroxynaphthalene-1-carbonyl)benzoic acid
• CAS: 25932-69-8
• 化学式: C₁₈H₁₂O₅
• 分子量: 308.29
• InChiKey: DAHPJJUGGRIGNZ-UHFFFAOYSA-N

物化性质

• 熔点：
  197-198 °C
• 沸点：
  598.8±40.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-<2,7-Dihydroxy-naphthoyl>-benzoesaeure 在 甲烷磺酸 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 6,18-Dihydroxyspiro[13-oxapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(14),3(12),4(9),5,7,10,15,17,19,21-decaene-2,3'-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
• 作为产物：
  描述：

  2-[2,7-Bis(methoxymethoxy)naphthalene-1-carbonyl]benzoic acid 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以94%的产率得到2-<2,7-Dihydroxy-naphthoyl>-benzoesaeure
  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

文献信息

• Exhaustive Syntheses of Naphthofluoresceins and Their Functions
  作者：Eriko Azuma、Naoko Nakamura、Kouji Kuramochi、Takahiro Sasamori、Norihiro Tokitoh、Ikuko Sagami、Kazunori Tsubaki

  DOI：10.1021/jo300177b

  日期：2012.4.6

  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.