4-azido-N-bis[amino(methyl)amino]phosphinothioyl-2,3,5,6-tetrafluorobenzamide | 217969-61-4

• 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: 4-azido-N-bis[amino(methyl)amino]phosphinothioyl-2,3,5,6-tetrafluorobenzamide
• CAS: 217969-61-4
• 化学式: C₉H₁₁F₄N₈OPS
• 分子量: 386.273
• InChiKey: ONQMFEOVRBIVJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  环己烷 、 4-azido-N-bis[amino(methyl)amino]phosphinothioyl-2,3,5,6-tetrafluorobenzamide 以 二氯甲烷 为溶剂， 反应 0.08h， 以73%的产率得到N-bis[amino(methyl)amino]phosphinothioyl-4-(cyclohexylamino)-2,3,5,6-tetrafluorobenzamide
  参考文献：
  名称：

  Chemistry of Bifunctional Photoprobes.¹ 3. Correlation between the Efficiency of CH Insertion by Photolabile Chelating Agents and Lifetimes of Singlet Nitrenes by Flash Photolysis:  First Example of Photochemical Attachment of ^99mTc−Complex with Human Serum Albumin

  摘要：

  Systematic functionalization of perfluoroaryl azides with chelating agents capable of complexing transition metals produces a new class of bifunctional photolabile chelating agents (BFPCAs). The strategy to shield the azide functionality from the electronic and steric influence of the electron-rich metal Pd through ester and amide bridges raised CH insertion efficiency to unprecedented levels (>92%) in a model solvent (cyclohexane). In contrast, perfluoroaryl azides attached to chelating agents via hydrazones show no significant CH insertion in cyclohexane upon photolysis. Measurements of the lifetimes of the singlet nitrenes derived from these agents by flash photolysis techniques correlate well with the efficiency of CH insertion by demonstrating longer lifetimes (10-50 times) for singlet nitrenes derived from azidotetrafluorinated esters and amides compared with the related hydrazones, which failed to yield significant CH insertion. A representative BFPCA 12 is chelated to diagnostic radionuclide Tc-94m and covalently attached to human serum albumin via photochemical activation extending the favorable bimolecular insertion characteristics of BFPCA to tracer level concentrations in buffer conditions. Flash photolysis experiments correlate singlet nitrene lifetimes with the efficiency of intermolecular insertion reactions. This work provides new photo-cross-linking technology, useful in radiodiagnostics and radiotherapy in nuclear medicine.

  DOI：

  10.1021/jo981458a
• 作为产物：
  描述：

  4-叠氮基-2,3,5,6-四氟苯甲酰胺 在 三乙胺 、 三氯氧磷 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 9.0h， 生成 4-azido-N-bis[amino(methyl)amino]phosphinothioyl-2,3,5,6-tetrafluorobenzamide
  参考文献：
  名称：

  Chemistry of Bifunctional Photoprobes.¹ 3. Correlation between the Efficiency of CH Insertion by Photolabile Chelating Agents and Lifetimes of Singlet Nitrenes by Flash Photolysis:  First Example of Photochemical Attachment of ^99mTc−Complex with Human Serum Albumin

  摘要：

  Systematic functionalization of perfluoroaryl azides with chelating agents capable of complexing transition metals produces a new class of bifunctional photolabile chelating agents (BFPCAs). The strategy to shield the azide functionality from the electronic and steric influence of the electron-rich metal Pd through ester and amide bridges raised CH insertion efficiency to unprecedented levels (>92%) in a model solvent (cyclohexane). In contrast, perfluoroaryl azides attached to chelating agents via hydrazones show no significant CH insertion in cyclohexane upon photolysis. Measurements of the lifetimes of the singlet nitrenes derived from these agents by flash photolysis techniques correlate well with the efficiency of CH insertion by demonstrating longer lifetimes (10-50 times) for singlet nitrenes derived from azidotetrafluorinated esters and amides compared with the related hydrazones, which failed to yield significant CH insertion. A representative BFPCA 12 is chelated to diagnostic radionuclide Tc-94m and covalently attached to human serum albumin via photochemical activation extending the favorable bimolecular insertion characteristics of BFPCA to tracer level concentrations in buffer conditions. Flash photolysis experiments correlate singlet nitrene lifetimes with the efficiency of intermolecular insertion reactions. This work provides new photo-cross-linking technology, useful in radiodiagnostics and radiotherapy in nuclear medicine.

  DOI：

  10.1021/jo981458a

文献信息

• Chemistry of Bifunctional Photoprobes.¹ 3. Correlation between the Efficiency of CH Insertion by Photolabile Chelating Agents and Lifetimes of Singlet Nitrenes by Flash Photolysis:  First Example of Photochemical Attachment of ^99mTc−Complex with Human Serum Albumin
  作者：Raghoottama S. Pandurangi、Przemyslaw Lusiak、Robert R. Kuntz、Wynn A. Volkert、Jacek Rogowski、Matthew S. Platz

  DOI：10.1021/jo981458a

  日期：1998.11.1

  Systematic functionalization of perfluoroaryl azides with chelating agents capable of complexing transition metals produces a new class of bifunctional photolabile chelating agents (BFPCAs). The strategy to shield the azide functionality from the electronic and steric influence of the electron-rich metal Pd through ester and amide bridges raised CH insertion efficiency to unprecedented levels (>92%) in a model solvent (cyclohexane). In contrast, perfluoroaryl azides attached to chelating agents via hydrazones show no significant CH insertion in cyclohexane upon photolysis. Measurements of the lifetimes of the singlet nitrenes derived from these agents by flash photolysis techniques correlate well with the efficiency of CH insertion by demonstrating longer lifetimes (10-50 times) for singlet nitrenes derived from azidotetrafluorinated esters and amides compared with the related hydrazones, which failed to yield significant CH insertion. A representative BFPCA 12 is chelated to diagnostic radionuclide Tc-94m and covalently attached to human serum albumin via photochemical activation extending the favorable bimolecular insertion characteristics of BFPCA to tracer level concentrations in buffer conditions. Flash photolysis experiments correlate singlet nitrene lifetimes with the efficiency of intermolecular insertion reactions. This work provides new photo-cross-linking technology, useful in radiodiagnostics and radiotherapy in nuclear medicine.