3,5-bis(dimethoxyphosphinylmethyl)benzoic acid | 223449-19-2

• 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: 3,5-bis(dimethoxyphosphinylmethyl)benzoic acid
• 英文别名: 3,5-bis[(dimethoxyphosphoryl)methyl]benzoic acid；5-carboxy-m-xylylenebisphosphonic acid tetramethyl ester；3,5-Bis(dimethoxyphosphorylmethyl)benzoic acid
• CAS: 223449-19-2
• 化学式: C₁₃H₂₀O₈P₂
• 分子量: 366.245
• InChiKey: WBIBRBZPWGXWAI-UHFFFAOYSA-N

物化性质

• 沸点：
  542.7±50.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,5-bis(dimethoxyphosphinylmethyl)benzoic acid 在 N-甲基吗啉 、 2-propanephosphonic acid anhydride 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ({[3,5-bis-(dimethoxy-phosphorylmethyl)-benzoyl]-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-benzyl]-amino}-methyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  RGD序列的第一个合成受体。

  摘要：

  [结构：见正文]优化的精氨酸受体单元与带有策略性放置的伯铵基团的半刚性接头的组合导致了第一个合成的RGD受体。它与游离RGD肽以及水中的cyclo（RGDfV）结合，缔合常数约为1000 M（-1）。RGD模拟物（例如苄am 6）未被识别，这使得新宿主成为对肽中的真实RGD序列具有选择性的新型受体的原型。

  DOI：

  10.1021/ol025976q
• 作为产物：
  描述：

  3,5-双(甲氧基羰基)苯甲酸 在 lithium hydroxide 、 三溴化磷 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 23.0h， 生成 3,5-bis(dimethoxyphosphinylmethyl)benzoic acid
  参考文献：
  名称：

  Synthesis of 3,5-bis(phosphonomethyl)benzoic acid and its application as a metal oxide surface bivalent anchor

  摘要：

  A protected form of 3,5-bis(phosphonomethyl)benzoic acid (Bpb-OH), a metal oxide surface bivalent anchor, has been synthesized, coupled to an amine functionality, deprotected, and shown to bind to metal oxide surfaces. The protected anchor, 3,5-bis(dimethoxyphosphinylmethyl)benzoic acid (Me(4)Bpb-OH) was synthesized in 23% yield over four steps, coupled to a proline-chromophore, deprotected with a solution of iodotrimethylsilane (TMSI) in acetonitrile and adsorbed to Tin(IV)-doped indium oxide and nanocrystalline TiO2 electodes at surface coverages of 1.5 x 10(-10) mol cm(-2) and 4.9 x 10(-11) mol cm(-2), respectively. Finally, Me(4)Bpb-OH was converted to an amino derivative by attaching a diamino butane linker. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00062-9

文献信息

• Entirely Artificial Signal Transduction with a Primary Messenger
  作者：Kai Bernitzki、Thomas Schrader

  DOI：10.1002/anie.200902973

  日期：2009.10.12

  I saw the sign: An artificial system allows messenger‐induced transmembrane signaling. External addition of a primary messenger molecule (DET, see picture) leads to formation of a heterodimeric complex of transmembrane units bearing tryptophan–dansyl (Trp–Dan) donor–acceptor pairs, which in turn stimulates a strong FRET on the opposite side of the membrane.

  我看到了这样的信号：人工系统允许信使诱导的跨膜信号传导。外部添加主要信使分子（DET，请参见图片）会导致形成带有色氨酸-丹磺酰基（Trp-Dan）供体-受体对的跨膜单元的异二聚体复合物，从而反过来刺激了对侧的强力FRET。膜。
• Bifunctional Bisamphiphilic Transmembrane Building Blocks for Artificial ­Signal Transduction
  作者：Thomas Schrader、Michael Maue、Kai Bernitzki、Manuel Ellermann

  DOI：10.1055/s-2008-1067155

  日期：2008.7

  A convergent modular total synthesis is described which affords bisamphiphilic bifunctional transmembrane building blocks useful for artificial signal transduction across membranes. The concept relies on direct Glaser-Hay coupling of lithocholic or cholenic acid propargyl esters, carrying recognition or signaling units on their opposite hydroxy functionalities. For catechol recognition, a 2-(amino

  描述了一种会聚模块化全合成，它提供了可用于跨膜人工信号转导的双两亲双功能跨膜构件。该概念依赖于石胆酸或胆酸炔丙基酯的直接 Glaser-Hay 偶联，在其相反的羟基官能团上携带识别或信号单元。对于儿茶酚识别，引入了 2-(氨基甲基)苯基硼酸，而铵醇则以双膦酸盐双阴离子为目标。信号单元分别包含一个 N-保护的半胱氨酸（硫醇亲核试剂）和一个 N-保护的半胱氨酸/吡啶二硫化物（二硫化物底物）。所有这些极性头基通过酯形成与脂质核心的羟基相连。
• Artificial Ditopic Arg-Gly-Asp (RGD) Receptors
  作者：Carsten Schmuck、Daniel Rupprecht、Matthias Junkers、Thomas Schrader

  DOI：10.1002/chem.200601821

  日期：2007.8.17

  fusion of two artificial recognition motifs for arginine and aspartate resulted in a new class of ditopic RGD receptor molecules, 1-4. The two binding sites for the oppositely charged amino acid residues are linked by either flexible linkers of different length (in 1-3) or a rigid aromatic spacer (in 4). These spacers are shown to be critical for the complexation efficiency of the artificial hosts. If

  精氨酸和天冬氨酸的两个人工识别基序的共价融合产生了一类新型的双位RGD受体分子1-4。带相反电荷的氨基酸残基的两个结合位点通过不同长度的柔性接头（在1-3中）或刚性芳族间隔基（在4中）相连。这些间隔物显示出对于人工宿主的络合效率至关重要。如果接头太柔韧性，如1-3中所示，则在宿主内发生不希望的分子内自缔合，并与底物结合竞争，从而削弱了底物的结合。4中的刚性芳族连接基可防止任何分子内自缔合，因此即使在缓冲水中也能观察到有效的RGD结合（缔合常数K（a）约为3000 m（-1））。如主体16所示，疏水性接触进一步增加 可以补充特定的库仑引力，从而导致更稳定的复合体（Ka = 5000 m（-1））。识别事件已通过NMR光谱，UV / Vis光谱和荧光滴定进行了研究。
• Efficient synthesis of water-soluble, phosphonate-terminated polyester dendrimers
  作者：Grzegorz M. Salamończyk

  DOI：10.1016/j.tetlet.2015.11.035

  日期：2015.12

  Simple and effective syntheses of novel, water-soluble, phosphonate-terminated polyester dendrimers varying in size and structure are described. These macromolecular compounds, consisting of thiophosphoric and 1,3,5-benzenetricarboxylic ester building blocks may find potential applications in health sciences as microbicides and/or as useful macromolecular models for functional coatings of superparamagnetic iron oxides (SPIOs) nanoparticles intended for use in hyperthermal therapy and magnetic resonance imaging (MRI). The dendrimers, possessing free phosphonate functional groups on the surface, were prepared in high yields from previously synthesized phosphorus-based substrates with 3,5-bis (dimethoxyphosphonyl)-methylibenzoic acid (4), being an essential precursor of the dendrimer polyanionic surface. In addition, an interesting example of virtual coupling between remote nuclei in the C-13 NMR spectrum of bisphosphonate monomer 3 was observed. (C) 2015 Elsevier Ltd. All rights reserved.