3'-oxo-3,11-bis(pivaloyloxy)-3'H-spiro[dibenzo[c,h]xanthene-7,1'-isobenzofuran]-6'-carboxylic acid | 1116583-26-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3'-oxo-3,11-bis(pivaloyloxy)-3'H-spiro[dibenzo[c,h]xanthene-7,1'-isobenzofuran]-6'-carboxylic acid
• CAS: 1116583-26-6
• 化学式: C₃₉H₃₂O₉
• 分子量: 644.678
• InChiKey: HXNRKHVCLVUOLO-UHFFFAOYSA-N

物化性质

• 沸点：
  839.0±65.0 °C(predicted)
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.16
• 重原子数：
  48.0
• 可旋转键数：
  3.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  125.43
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-哌啶乙醇 、 3'-oxo-3,11-bis(pivaloyloxy)-3'H-spiro[dibenzo[c,h]xanthene-7,1'-isobenzofuran]-6'-carboxylic acid 在 N-乙基吗啉 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以45.9%的产率得到6'-(4-(2-hydroxyethyl)piperidine-1-carbonyl)-3'-oxo-3'H-spiro[dibenzo[c,h]xanthene-7,1'-isobenzofuran]-3,11-diyl bis(2,2-dimethylpropanoate)
  参考文献：
  名称：

  The use of 6-carboxynaphthofluorescein phosphoramidite in the automated synthesis of quencher-dye oligonucleotide probes (QDOPs)

  摘要：

  Real-time detection and quantitation of specific amplicons have been achieved using quencher and dye-labeled oligonucleotides such as molecular beacons. The molecular beacon molecule has a fluorescent reporter dye at the T-end and a quencher at the 3'-end. When the closed molecular beacon is excited by irradiation, the reporter fluorescence is greatly reduced by quenching through the process of fluorescence resonance energy transfer. When the molecular beacon hybridizes to the target, the stem loop opens making the fluorophore and quencher spatially distinct, thus increasing the reporter dye fluorescence intensity. Labeling of dyes to T-end of oligonucleotides has been done typically using manual methods, it is possible to do manual coupling at the milligram scale. Described here is the development of a scalable process for oligonucleotide labeling, which is robust, and has been achieved for 6-carboxynaphthofluorescein by connecting it to a corresponding phosphoramidite [Theisen, P.; McCollum, C.: Upadhya, K.; Jacobson. K.: Vu, H.; Andrus, A.; Tetrahedron Lett. 1992, 33, 5033-5036]. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2008.11.059