Dimethyl 2',4'a-dimethylspiro[fluorene-9,5'-pyrrolo[1,2-b]pyridazine]-6',7'-dicarboxylate | 106960-53-6

• 分子结构分类: 有机化合物
• 英文名称: Dimethyl 2',4'a-dimethylspiro[fluorene-9,5'-pyrrolo[1,2-b]pyridazine]-6',7'-dicarboxylate
• CAS: 106960-53-6
• 化学式: C₂₅H₂₂N₂O₄
• 分子量: 414.461
• InChiKey: RLFMTTICYCRZGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Dimethyl 2',4'a-dimethylspiro[fluorene-9,5'-pyrrolo[1,2-b]pyridazine]-6',7'-dicarboxylate 生成 、
  参考文献：
  名称：

  Photophysical Properties of Biphotochromic Dihydroindolizines. Ring-Opening into Extended Bis-Betaines

  摘要：

  New photochromic spirodihydroindolizines (DHI) that are mono-(1a-e) or biphotochromic (3a-e) have been prepared. The monophotochromic DHIs 1d and 1e contain sterically highly demanding substituents. Photophysical studies, both static and Lime-resolved, were carried out with 1 and 3. Monophotochromic DHIs 1a-e show fluorescence and phosphorescence. Temperature decrease produces a hypsochromic shift in the fluorescence spectra. Time-resolved studies demonstrate that the photochromism is based on a one-photon electrocyclic photoreaction of 1 to the colored betaine. Only one transient of 0.6-6 mu s lifetime could be detected for the transformation of 1a-e. For the bichromophoric DHIs 3a-e, two different transients were recorded with lifetimes of 1 and 45-680 mu s. It was proved that the ring opening 1 --> 4 (as well as 3 --> 9) results from an excited singlet species, as demonstrated by the absence of an oxygen effect and by sensitization experiments. Viscosity effects underline the conformational transformations involved in the sequence 1 --> T --> 4 and 3 --> T-1 --> T-2 --> 9 to occur in distinct steps, thus showing the detailed reaction paths of photochromic molecules 1 and 3.

  DOI：

  10.1021/jo971182r
• 作为产物：
  描述：

  betaine 297 以 正戊烷 为溶剂， 生成 Dimethyl 2',4'a-dimethylspiro[fluorene-9,5'-pyrrolo[1,2-b]pyridazine]-6',7'-dicarboxylate
  参考文献：
  名称：

  Solvent effects on the thermal reaction of photochromic dihydroindolizines: Friction or polarizability effect within the alkanes

  摘要：

  The thermal reaction to a photochromic dihydroindolizine was studied in six alkane solutions. The reaction rate in the branched iso-octane compared to that in n-alkanes shows a distinct effect of the molecular shape of the solvent. This effect could be rationalized both by solvent friction as well as by solvent polarizability effects. The rates in all the alkanes, however, form a linear correlation to the π* polarity parameter of Kamlet and Taft, indicating, that the change of polarizability within the alkanes is the ‘‘true’’ reason for the observed solvent dependence. The well-known fact that macroscopic properties are not able to reflect microscopic influences (like molecular shape, e.g.) is valid for friction (when comparing shear viscosity with rotational relaxation times) as well as for polarity (when comparing the Onsager reaction field with π*). The reaction shows a negative temperature trend of the Arrhenius activation energy. Attempts are made to explain this by a composed mechanism, including a partial rotation prior to the final ring closure.

  DOI：

  10.1063/1.463011

文献信息

• WATER SOLUBLE PHOTOCHROMIC COMPOUNDS FOR LABELING OF BIOMOLECULES AND METHOD FOR DETECTING BIOMOLECULES USING THE SAME
  申请人：Chung Bong Hyun

  公开号：US20100256397A1

  公开（公告）日：2010-10-07

  The present invention relates to water-soluble photochromic compounds for labeling biomolecules and a method of detecting biomolecules using the same. More specifically, relates to water-soluble photochromic compounds for labeling biomolecules, in which a functional group rendering photochromic molecules water-soluble is linked to a functional group capable of binding to biomolecules, and a method of detecting biomolecules using the same. Because the disclosed water-soluble photochromic compounds exhibit the color corresponding to the wavelength of visible light range, they allow signals to be easily detected not only with an UV-VIS spectrophotometer but also visually. Accordingly, the photochromic compounds can be advantageously used in sensors for diagnosing diseases.

  本发明涉及用于标记生物分子的水溶性光致变色化合物以及使用它们检测生物分子的方法。更具体地，涉及用于标记生物分子的水溶性光致变色化合物，其中将使光致分子水溶性的功能基团与能够与生物分子结合的功能基团连接在一起，并且使用它们检测生物分子的方法。由于所披露的水溶性光致变色化合物表现出与可见光范围内波长相对应的颜色，因此它们不仅可以使用紫外-可见光谱仪轻松检测信号，而且还可以直观地检测。因此，这些光致变色化合物可以在诊断疾病的传感器中有优势地使用。
• US8415472B2
  申请人：——

  公开号：US8415472B2

  公开（公告）日：2013-04-09