bis(8-carboxy-2,2,6,6-tetramethylbenzo-[1,2-d:4,5-d′]bis[1,3]dithiol-4-yl)(2,2,6,6-tetramethyl-8-phosphonobenzo[1,2-d:4,5-d′]bis[1,3]-dithiol-4-yl)methyl | 1429402-44-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: bis(8-carboxy-2,2,6,6-tetramethylbenzo-[1,2-d:4,5-d′]bis[1,3]dithiol-4-yl)(2,2,6,6-tetramethyl-8-phosphonobenzo[1,2-d:4,5-d′]bis[1,3]-dithiol-4-yl)methyl
• CAS: 1429402-44-7
• 化学式: C₃₉H₄₀O₇PS₁₂
• 分子量: 1036.51
• InChiKey: BJSWTMOHRSTYFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.51
• 重原子数：
  59.0
• 可旋转键数：
  6.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  132.13
• 氢给体数：
  4.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  bis(8-carboxy-2,2,6,6-tetramethylbenzo-[1,2-d:4,5-d′]bis[1,3]dithiol-4-yl)(8-diethoxyphosphoryl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d′]-bis[1,3]dithiol-4-yl)methyl 在 二氯甲烷 、 bromo(trimethylsilyl)silane 、 甲醇 作用下， 以 四氢呋喃 、 三乙胺 为溶剂， 反应 75.0h， 以88%的产率得到bis(8-carboxy-2,2,6,6-tetramethylbenzo-[1,2-d:4,5-d′]bis[1,3]dithiol-4-yl)(2,2,6,6-tetramethyl-8-phosphonobenzo[1,2-d:4,5-d′]bis[1,3]-dithiol-4-yl)methyl
  参考文献：
  名称：

  A Simple and Convenient Synthesis of a Multifunctional Spin Probe, Phosphonate Derivative of a Persistent Radical of the Triarylmethyl Series

  摘要：

  DOI：

  10.1134/s107042802106004x

文献信息

• Phosphonated Trityl Probes for Concurrent in Vivo Tissue Oxygen and pH Monitoring Using Electron Paramagnetic Resonance-Based Techniques
  作者：Ilirian Dhimitruka、Andrey A. Bobko、Timothy D. Eubank、Denis A. Komarov、Valery V. Khramtsov

  DOI：10.1021/ja401572r

  日期：2013.4.17

  Previously we proposed the concept of dual function pH and oxygen paramagnetic probes based on the incorporation of ionizable groups into the structure of persistent triarylmethyl radicals, TAMs (J. Am. Chem. Soc. 2007, 129, 7240-7241). In this paper, we synthesized an asymmetric monophosphonated TAM probe with the simplest doublet hfs pattern ideally suited for dual function electron paramagnetic resonance (EPR)-based applications. An extraordinary low line width of the synthesized deuterated derivative, p(1)TAM-D (Delta H-pp <= 50 mG, Lorentz line width, <= 20 mG) results in high sensitivity to pO(2) due to oxygen-induced line broadening (Delta LW/Delta pO(2) approximate to 0.5 mG/mmHg or approximate to 400 mG/mM); accuracy of pO(2) measurement, approximate to 1 mmHg). The presence of a phosphono group in the p(1)TAM-D structure provides pH sensitivity to its EPR spectra in the physiological range of pH from 5.9 to 8.2 with the ratio of signal intensities of protonated and deprotonated states being a reliable pH marker (accuracy of pH measurements, +/- 0.05). The independent character of pH and [O-2] effects on the EPR spectra of p(1)TAM-D provides dual functionality to this probe. The L-band EPR studies performed in breast tumor-bearing mice show a significant difference in extracellular pH and pO(2) between tumor and normal mammary gland tissues, as well as the effect of animal breathing with 100% O-2 on tissue oxygenation. The developed dual function phosphonated p(1)TAM-D probe provides a unique tool for in vivo concurrent tissue oxygen and pH monitoring.