5-hydroxynaphthalene-1,3-dicarbaldehyde | 1440970-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-hydroxynaphthalene-1,3-dicarbaldehyde
• CAS: 1440970-35-3
• 化学式: C₁₂H₈O₃
• 分子量: 200.194
• InChiKey: NOEYHYAFEHJNQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-hydroxynaphthalene-1,3-dicarbaldehyde 、 N-(3-sulfonatopropyl)-2,3,3-trimethyl-3H-indolium 在 sodium acetate 、 potassium carbonate 作用下， 以 乙酸酐 、 甲醇 为溶剂， 反应 0.5h， 以21%的产率得到3,3'-(((5-hydroxynaphthalene-1,3-diyl)bis(ethene-2,1-diyl))bis(3,3-dimethyl-3H-indole-1-ium-2,1-diyl))bis(propane-1-sulfonate)
  参考文献：
  名称：

  New repertoire of ‘donor-two-acceptor’ NIR fluorogenic dyes

  摘要：

  Dye molecules with various fluorescent wavelengths are widely used for diagnostic and optical imaging applications. Accordingly, there is a constant demand for fluorogenic dyes with new properties. We have recently developed a novel strategy for the design of long-wavelength fluorescent dyes with a turn-ON option. The design is based on a donor-two-acceptor pi-electron system that can undergo an internal charge transfer to form a new fluorochrome with an extended pi-conjugated system. Here, we describe a series of such dyes based on two novel latent donors, naphthol and hydroxycoumarin. One of the dyes has showed excellent near-infrared fluorescent characteristics and specifically was demonstrated as a mitochondrial imaging reagent in live cells. This unique strategy for fluorogenic dye design has opened new doors for further near-infrared fluorescence probe discovery. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.049
• 作为产物：
  描述：

  5,7-Dimethyl-naphthol-(1) 在 4-二甲氨基吡啶 、 manganese(IV) oxide 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 silver sulfate 、 三乙胺 、 过氧化苯甲酰 作用下， 以 1,4-二氧六环 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 4.67h， 生成 5-hydroxynaphthalene-1,3-dicarbaldehyde
  参考文献：
  名称：

  New repertoire of ‘donor-two-acceptor’ NIR fluorogenic dyes

  摘要：

  Dye molecules with various fluorescent wavelengths are widely used for diagnostic and optical imaging applications. Accordingly, there is a constant demand for fluorogenic dyes with new properties. We have recently developed a novel strategy for the design of long-wavelength fluorescent dyes with a turn-ON option. The design is based on a donor-two-acceptor pi-electron system that can undergo an internal charge transfer to form a new fluorochrome with an extended pi-conjugated system. Here, we describe a series of such dyes based on two novel latent donors, naphthol and hydroxycoumarin. One of the dyes has showed excellent near-infrared fluorescent characteristics and specifically was demonstrated as a mitochondrial imaging reagent in live cells. This unique strategy for fluorogenic dye design has opened new doors for further near-infrared fluorescence probe discovery. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.049