(diethoyphosphinyldifluoromethyl)benzoic acid | 189393-75-7

• 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: (diethoyphosphinyldifluoromethyl)benzoic acid
• 英文别名: 4-((diethoxyphosphoryl)difluoromethyl)benzoic acid；4-[(Diethoxy-phosphoryl)-difluoro-methyl]-benzoic acid；4-[diethoxyphosphoryl(difluoro)methyl]benzoic acid
• CAS: 189393-75-7
• 化学式: C₁₂H₁₅F₂O₅P
• 分子量: 308.219
• InChiKey: DRVWIRGROHAHPD-UHFFFAOYSA-N

物化性质

• 沸点：
  411.8±45.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (diethoyphosphinyldifluoromethyl)benzoic acid 在 三乙基硅烷 、 三甲基溴硅烷 、 Rink-NH₂ resin 、 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  通过Ugi四组分缩合固相合成潜在的蛋白质酪氨酸磷酸酶抑制剂。

  摘要：

  使用Rink-NH2树脂，4-[（（二乙氧基膦酰基）二氟甲基]苯甲酸）和18种醛和6种异腈进行Ugi四组分缩合，制备了108个α，α-二氟亚甲基膦酸文库。树脂裂解后，将二乙基膦酸酯用三甲基甲硅烷基溴水解，得到游离酸，将其测定对PTPα，PTPβ和PTPε的抑制。

  DOI：

  10.1016/s0960-894x(98)00408-9
• 作为产物：
  描述：

  溴氟甲基膦酸二乙酯 在 palladium 10% on activated carbon 、 氢气 、 镉 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 23.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 (diethoyphosphinyldifluoromethyl)benzoic acid
  参考文献：
  名称：

  Structure-Guided Design, Synthesis, and Evaluation of Guanine-Derived Inhibitors of the eIF4E mRNA–Cap Interaction

  摘要：

  The eukaryotic initiation factor 4E (eIF4E) plays a central role in the initiation of gene translation and subsequent protein synthesis by binding the 5' terminal mRNA cap structure. We designed and synthesized a series of novel compounds that display potent binding affinity against eIF4E despite their lack of a ribose moiety, phosphate, and positive charge as present in m7-GMP. The biochemical activity of compound 33 is 95 nM for eIF4E in an SPA binding assay. More importantly, the compound has an IC50 of 2.5 mu M for inhibiting cap-dependent mRNA translation in a rabbit reticular cell extract assay (RRL-IVT). This series of potent, truncated analogues could serve as a promising new starting point toward the design of neutral eIF4E inhibitors with physicochemical properties suitable for cellular activity assessment.

  DOI：

  10.1021/jm300037x

文献信息

• Cuprous chloride promoted coupling reaction of diethoxyphosphinyldifluoromethylcadmium reagent with aryl iodides: A practical and convenient preparation of α,α-difluoro benzylic phosphonates
  作者：Weiming Qiu、Donald J. Burton

  DOI：10.1016/j.jfluchem.2013.04.008

  日期：2013.11

  cross coupling reaction of diethoxyphosphinyldifluoromethylcadmium reagent with aryl iodides was promoted by CuCl under mild conditions to give α,α-difluoro benzylic phosphonates in good yields. A variety of functional groups, including halides, phosphonate, nitro, ketone, carboxylic acid and ester in aryl iodides, could be tolerated. This methodology has been successfully applied to prepare α,α-difluoro

  CuCl在温和的条件下促进了二乙氧基次膦基二氟甲基镉试剂与芳基碘的交叉偶联反应，从而以高收率得到了α，α-二氟苄基膦酸酯。可以容许包括芳基碘化物中的卤化物，膦酸酯，硝基，酮，羧酸和酯在内的多种官能团。该方法已经成功地用于制备α，α-二氟Fostedil 9。
• Compounds, compositions and methods for inhibiting the binding of
  申请人：Warner-Lambert Company

  公开号：US05922697A1

  公开（公告）日：1999-07-13

  The present invention provides compounds that inhibit the binding of proteins containing an SH2 domain to cognate phosphorylated proteins. The invention also provides pharmaceutical compositions containing the compounds and methods of inhibiting the binding of proteins containing an SH2 domain to cognate phosphorylated proteins.

  本发明提供了抑制含有SH2结构域的蛋白质与同源磷酸化蛋白质结合的化合物。本发明还提供了含有该化合物的药物组合物以及抑制含有SH2结构域的蛋白质与同源磷酸化蛋白质结合的方法。
• Fragment-based discovery of selective inhibitors of the Mycobacterium tuberculosis protein tyrosine phosphatase PtpA
  作者：Katherine A. Rawls、P. Therese Lang、Jun Takeuchi、Shinichi Imamura、Tyler D. Baguley、Christoph Grundner、Tom Alber、Jonathan A. Ellman

  DOI：10.1016/j.bmcl.2009.10.090

  日期：2009.12

  The development of low mu M inhibitors of the Mycobacterium tuberculosis phosphatase PtpA is reported. The most potent of these inhibitors (K-i = 1.4 +/- 0.3 mu M) was found to be selective when tested against a panel of human tyrosine and dual-specificity phosphatases (11-fold vs the highly homologous HCPtpA, and >70-fold vs all others tested). Modeling the inhibitor-PtpA complexes explained the structure-activity relationships observed in vitro and revealed further possibilities for compound development. (C) 2009 Elsevier Ltd. All rights reserved.
• US5922697A
  申请人：——

  公开号：US5922697A

  公开（公告）日：1999-07-13