7-Hydroxy-2-oxochromene-3,8-dicarbaldehyde | 1440970-41-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-Hydroxy-2-oxochromene-3,8-dicarbaldehyde
• CAS: 1440970-41-1
• 化学式: C₁₁H₆O₅
• 分子量: 218.166
• InChiKey: INPKYPXWZLOABX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-Hydroxy-2-oxochromene-3,8-dicarbaldehyde 在 四氢吡咯 、 哌啶 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成
  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：

  在 sodium periodate 、 四氧化锇 、 silica gel 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 10.5h， 生成 7-Hydroxy-2-oxochromene-3,8-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

文献信息

• Ultrafast excited-state proton transfer from hydroxycoumarin-dipicolinium cyanine dyes
  作者：Ron Simkovitch、Einat Kisin-Finfer、Shay Shomer、Rinat Gepshtein、Doron Shabat、Dan Huppert

  DOI：10.1016/j.jphotochem.2013.01.004

  日期：2013.2

  The photoprotolytic properties of a recently synthesized photoacid, hydroxycoumarin-dipicolinium salt (HCD) were studied by means of time-resolved emission techniques. We found that HCD is a super-photoacid with pK*(a) < -2 and with an excited-state proton transfer to water with a rate constant of k(PT) = 1.4 x 10(11) s(-1). We also found that HCD undergoes ESPT in a large number of protic solvents. The kinetic isotope effect is about two for water, methanol and ethanol. (C) 2013 Elsevier B.V. All rights reserved.