1-Dichlorophosphoryloxy-3-(trifluoromethyl)benzene | 6780-90-1

• 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: 1-Dichlorophosphoryloxy-3-(trifluoromethyl)benzene
• CAS: 6780-90-1
• 化学式: C₇H₄Cl₂F₃O₂P
• 分子量: 278.983
• InChiKey: NQHCHMGXCLWELR-UHFFFAOYSA-N

物化性质

• 沸点：
  185 °C(Press: 17 Torr)
• 密度：
  1.572±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-Dichlorophosphoryloxy-3-(trifluoromethyl)benzene 在 叔丁基氯化镁 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 2′,3′-didehydro-2′,3′-dideoxythymidine-5′(4-(trifluoromethyl)phenyl methoxy alaninylphosphate)
  参考文献：
  名称：

  Polyfluoroaromatic stavudine (d4T) ProTides exhibit enhanced anti-HIV activity

  摘要：

  Human Immunodeficiency Virus (HIV) damages the immune system and leads to the life-threatening acquired immunodeficiency syndrome (AIDS). Despite the advances in the field of antiretroviral treatment, HIV remains a major public health challenge.Nucleosides represent a prominent chemotherapeutic class for treating viruses, however their cellular uptake, kinase-mediated activation and catabolism are limiting factors. Herein, we report the synthesis and in vitro evaluation of stavudine (d4T) ProTides containing polyfluorinated aryl groups against two strains; HIV-1 (IIIB) and HIV-2 (ROD). ProTide 5d containing a meta-substituted pentafluorosulfanyl (3-SF5) aryl group showed superior antiviral activity over the parent d4T and the nonfluorinated analogue 5a. ProTide 5d has low nano-molar antiviral activity; (IC50=30 nM, HIV-1) and (IC50=36 nM, HIV-2) which is over tenfold more potent than d4T. Interestingly, ProTide 5d showed a significantly high selectivity indices with SI=1753 (HIV-1) and 1461 (HIV-2) which is more than twice that of the d4T. All ProTides were screened in wild type as well as thymidine kinase deficient (TK-) cells. Enzymatic activation of ProTide 5d using carboxypeptidase Y enzyme and monitored using both P-31 and F-19 NMR is presented.

  DOI：

  10.1016/j.bmcl.2019.126721
• 作为产物：
  描述：

  间三氟甲基苯酚 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 1-Dichlorophosphoryloxy-3-(trifluoromethyl)benzene
  参考文献：
  名称：

  氨基磷酸酯ProTide技术的应用显着提高了碳环腺苷衍生物的抗病毒效力。

  摘要：

  我们报告了氨基磷酸酯原核苷酸（ProTide）技术在抗病毒剂碳环L-d4A（L-Cd4A）中的应用。L-Cd4A的苯基甲基丙氨酸基母体ProTide是通过格利雅（Grignard）介导的磷酰氯反应制备的，得到的化合物具有显着改善的抗HIV（2600倍）和HBV活性。我们描述了ProTide的芳基，酯和氨基酸区域的修饰，以及这些变化如何影响抗病毒活性和代谢稳定性。注意到针对HIV和HBV的SAR分别且不同。另外，由D-核苷D-Cd4A和双脱氧类似物L-CddA和D-CddA制备ProTide。与母体药物相比，这些化合物显示出更适度的效能改善。综上所述，当将ProTide方法应用于L-Cd4A时，在体外的效价提高了9000倍，非常成功，抗HIV的能力提高了。为了临床前候选人的选择，我们使用食蟹猴肝脏和肠道S9馏分进行了代谢稳定性研究。

  DOI：

  10.1021/jm060776w

文献信息

• Hydrogen phosphates: Self initiated organocatalysts for the controlled ring-opening polymerization of cyclic esters
  作者：Payal Malik、Debashis Chakraborty

  DOI：10.1016/j.ica.2013.02.006

  日期：2013.5

  A series of arylhydrogenphosphates and aryldihydrogenphosphates was synthesized and characterized using spectroscopic methods and single crystal X-ray diffraction. These compounds were assessed as catalysts towards the ring-opening polymerization and proved to be potent organocatalysts for the ring-opening polymerization of cyclic esters. The bulk polymerizations were performed in the absence of external initiator. The polymerization proceeds in a controlled fashion which leads to well defined polyesters with narrow molecular weight distributions. In the post polymerization experiments, kinetics, mechanism and monomer concentration effects were investigated. The kinetic results have confirmed the pseudo-living character of the polymerizations and mechanistic studies suggest that the polymerization operates through a cationic mechanism. (C) 2013 Elsevier B.V. All rights reserved.
• GORYUNOV, E. I.;PETROVSKIJ, P. V.;ZAXAROV, L. S.;KABACHNIK, M. I., IZV. AN CCCP. CEP. XIM.,(1990) N, S. 433-441
  作者：GORYUNOV, E. I.、PETROVSKIJ, P. V.、ZAXAROV, L. S.、KABACHNIK, M. I.

  DOI：——

  日期：——