5-methoxycarbonyl-m-xylylene bisphosphonic acid tetramethyl ester | 223449-25-0

• 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: 5-methoxycarbonyl-m-xylylene bisphosphonic acid tetramethyl ester
• 英文别名: methyl 3,5-bis(dimethoxyphosphinylmethyl)benzoate；Methyl 3,5-bis(dimethoxyphosphorylmethyl)benzoate
• CAS: 223449-25-0
• 化学式: C₁₄H₂₂O₈P₂
• 分子量: 380.271
• InChiKey: YBFNBBUMKOURON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-methoxycarbonyl-m-xylylene bisphosphonic acid tetramethyl ester 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 、 lithium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 10.08h， 生成
  参考文献：
  名称：

  Efficient synthesis of water-soluble, phosphonate-terminated polyester dendrimers

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2015.11.035
• 作为产物：
  描述：

  3,5-双(甲氧基羰基)苯甲酸 在 三溴化磷 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 5-methoxycarbonyl-m-xylylene bisphosphonic acid tetramethyl ester
  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

• Optimization of a Synthetic Arginine Receptor. Systematic Tuning of Noncovalent Interactions
  作者：Stephan Rensing、Markus Arendt、Andreas Springer、Thomas Grawe、Thomas Schrader

  DOI：10.1021/jo0156161

  日期：2001.8.1

  The simple arginine binder I could be optimized by strengthening pi -cation as well as electrostatic interactions. Electron-donating or -withdrawing substituents in the 5-position provide experimental evidence for T-cation interactions, because binding energies increase by up to 0.6 kcal/mol due to a single benzene - guanidinium interaction. Even more effective is the introduction of a third phosphonate functionality at the correct distance, so that the guanidinium cation is recognized by optimal electrostatic and hydrogen bond interactions. Monte Carlo simulations and NOESY experiments confirm the expected complex geometries. The optimized host molecule 8 binds arginine half an order of magnitude more efficiently than the parent molecule.