1,3,5-tris(diisopropyl phosphonate)benzene | 728005-70-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 1,3,5-tris(diisopropyl phosphonate)benzene
• 英文别名: 1,3,5-C6H3[PO(OiPr)2]3；1,3,5-Tris[di(propan-2-yloxy)phosphoryl]benzene
• CAS: 728005-70-7
• 化学式: C₂₄H₄₅O₉P₃
• 分子量: 570.537
• InChiKey: VEQBHWJLRRKHGE-UHFFFAOYSA-N

物化性质

• 沸点：
  598.5±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,3,5-tris(diisopropyl phosphonate)benzene 在 盐酸 作用下， 以 水 为溶剂， 生成 (3,5-二膦酰基苯基)膦酸
  参考文献：
  名称：

  New layered copper 1,3,5-benzenetriphosphonates pillared with N-donor ligands: their synthesis, crystal structures, and adsorption properties

  摘要：

  合成了新的分层状铜磷酰化物，并研究了其对N-供体支撑配体的吸附性能。

  DOI：

  10.1039/c5dt01137j
• 作为产物：
  描述：

  三异丙基亚磷酸酯 、 1,3,5-三溴苯 在 nickel dibromide 作用下， 以 均三甲苯 为溶剂， 反应 1.0h， 以82%的产率得到1,3,5-tris(diisopropyl phosphonate)benzene
  参考文献：
  名称：

  Synthesis and structure of and DFT-studies on 1,3,5-[P(O)(i-PrO)2]3C6H3 and its CHCl3 adduct: analysis of the Cl3C–H⋯OP hydrogen bond

  摘要：

  The novel triphosphonic ester 1,3,5-[P(O)(i-PrO)(2)](3)C6H3 (1) was synthesized and fully characterized including single crystal X-ray diffraction analysis. Crystallization in the presence of CHCl3 gave the corresponding solvate, 1.CHCl3, which shows moderate C-H...OP hydrogen bonding. The hydrogen bond strength in 1.CHCl3 and the model compound [P(O)(i-PrO)(2)]C6H5.CHCl3 (2.CHCl3) were analyzed using RHF, DFT and MP2 methods. The calculated C-H...OP hydrogen bond strength is in the range 5-6 kcal mol(-1), which is comparable with hydrogen bond strength in the water dimer but higher than in comparable C-H...OC aggregates. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2004.04.013

文献信息

• Scalable synthesis of multi-substituted aryl-phosphonates: Exploring the limits of isoretical expansion and the synthesis of new triazene-based phosphonates
  作者：Derek Barbee、Andrew R. Barron

  DOI：10.1080/10426507.2019.1673750

  日期：2020.3.3

  the efficiency of the palladium-catalyzed Hirao cross-coupling reaction in the synthesis of substituted phosphonates; however, attempts to prepare derivatives with isoretical expansion through the cyclization of 4-(4′-bromophenyl)acetophenone resulted in an extremely low yield, with the isolation of the dimer intermediate. Ab initio calculations showed that while the trimerization of acetophenone is

  摘要 新型多取代芳基膦酸酯化合物的开发有望成为具有优异孔隙率和气体吸附性能的金属有机骨架 (MOF) 材料的新构件。我们证明了钯催化的 Hirao 交叉偶联反应在取代膦酸酯的合成中的效率；然而，尝试通过 4-(4'-溴苯基) 苯乙酮的环化制备具有等距扩展的衍生物的尝试导致极低的产率，并分离出二聚体中间体。从头算计算表明，虽然苯乙酮的三聚是放热的，但 4-苯基苯乙酮的三聚是吸热的。相比之下，4-(4'-溴苯基) 苄腈的环化是放热的，并允许形成适当的膦酸。苄腈方法还允许形成具有高位阻的邻甲基衍生物。本文报道的所有多取代芳基膦酸酯化合物都可以在多克规模上制备，使研究人员能够为膦酸酯 MOF 提供更广泛的构建模块。图形概要
• Two‐ and Three‐Dimensional Hydrogen‐Bonded Networks Built from 1,3,5‐[(HO) ₂ (O)P] ₃ C ₆ H ₃ and 4‐(Dimethylamino)pyridine
  作者：Michael Mehring

  DOI：10.1002/ejic.200300843

  日期：2004.8

  gave [1-(HO)2(O)P}-3,5-(HO)(O)2P}2C6H3]2−[4-(Me2N)C5H4NH}+]2 (2) and [1,3-(HO)2(O)P}2-5-(HO)(O)2P}C6H3]−[4-(Me2N)C5H4NH]+ (3). Single-crystal X-ray diffraction analyses revealed a two- and a three-dimensional hydrogen-bonded network for compounds 2 and 3, respectively. Compound 2 is composed of layers which are formed by hydrogen-bonded motifs of the type R2,2(8) and R4,4(16). These motifs are

  3,5-双(膦酰基苯基)膦酸，1,3,5-[(HO)2(O)P]3C6H3，在 4-(二甲氨基)吡啶，4-(Me2N)存在下从 MeOH/H2O 中结晶)C5H4N，得到 [1-(HO)2(O)P}-3,5-(HO)(O)2P}2C6H3]2−[4-(Me2N) H}+]2 (2) [1,3-(HO)2(O)P}2-5-(HO)(O)2P}C6H3]-[4-(Me2N) H]+(3)。单晶 X 射线衍射分析分别揭示了化合物 2 和 3 的二维和三维氢键网络。化合物 2 由由 R2,2(8) 和 R4,4(16) 型氢键基序形成的层组成。这些基序通过额外的氢键和苯间隔物在层内连接。阳离子 [4-(Me2N) H]+ 位于层之间，决定了大约 6.5 A 的层间间距。在化合物 3 中，观察到氢键结构单元 R2,3(10) 的层状网络。这些单元通过网络内的四个额外
• Arylphosphonic acid esters as bridging ligands in coordination polymers of bismuth
  作者：Dirk Mansfeld、Christina Dietz、Tobias Rüffer、Petra Ecorchard、Colin Georgi、Heinrich Lang、Markus Schürmann、Klaus Jurkschat、Michael Mehring

  DOI：10.1515/mgmc-2013-0047

  日期：2013.1.1

  The reaction of the arylphosphonic acid esters 4,4'-[(i-PrO)(2)P(O)]C6H4C6H4[P(O)(Oi-Pr)(2)] (L-1), 1,3,5-[(i-PrO)(2)P(O)](3)C6H3 (L-2), and 5-t-Bu-1,3-[(i-PrO)(2)P(O)](2)C6H3 (L-3), respectively, with bismuth halides BiX3 (X = Cl, Br, I) gave seven novel bismuth coordination polymers that have been characterized by single-crystal X-ray diffraction analysis. The solid-state structures of [(BiCl3)(L-1)] (1), [(BiBr3)(L-1)]center dot 0.25CH(3)CN (2 center dot 0.25CH(3)CN), [(BiI3)(2)(L-1)]center dot 0.25CH(3)CN (3 center dot 0.25CH(3)CN), [(BiCl3)(L-2)] (4), [(BiCl3)(2)(L-2)] (5), [(BiBr3)(2) (L-2)]center dot CH3CN (6 center dot CH3CN), and [(BiCl3)(L-3)] (7) are presented. Thermal analysis of [(BiCl3)(2)(L-2)] (5) is indicative of a conversion of the complexes into a bismuth phosphonate by complete i-PrX elimination, whereas for [(BiBr3)(2)(L-2)] (6), elimination of i-PrBr and BiBr3 is assumed. Compounds 1-3 form one-dimensional coordination polymers, whereas two-dimensional networks are observed for compounds 4-7.