methylenebisphosphonic acid P,P'-di[3-(trimethylsilyl)propyl] diester | 282541-11-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: methylenebisphosphonic acid P,P'-di[3-(trimethylsilyl)propyl] diester
• 英文别名: P,P'-di(3-(trimethylsilyl)propyl) methylenebisphosphonic acid；P,P'-di[3-(trimethylsilyl)-1-propyl]methylenediphosphonicacid；di-[3-(trimethylsilyl)-1-propylene]methylenediphosphonic acid；methylenebis(3-(trimethylsilyl)propyl hydrogen phosphonate)；Bis[3-(trimethylsilyl)propyl] methylenebisphosphonate；[hydroxy(3-trimethylsilylpropoxy)phosphoryl]methyl-(3-trimethylsilylpropoxy)phosphinic acid
• CAS: 282541-11-1
• 化学式: C₁₃H₃₄O₆P₂Si₂
• 分子量: 404.528
• InChiKey: NVYFENZYHYYFQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  europium(III) nitrate hexahydrate 、 methylenebisphosphonic acid P,P'-di[3-(trimethylsilyl)propyl] diester 在 HNO₃ 作用下， 以 甲醇 为溶剂， 以93%的产率得到Eu2(P,P'-di[3-(trimethylsilyl)-1-propyl]methylenediphosphonate)3
  参考文献：
  名称：

  SYNTHESIS AND CHARACTERIZATION OF METAL COMPLEXES OF P,P′-DI[3-(TRIMETHYLSILYL)-1-PROPYL] METHYLENEDIPHOSPHONIC ACID

  摘要：

  The silicon-substituted diphosphonic acid P,P'-di[3-(trimethylsilyl)-1-propyl] methylenediphosphonic acid, H2DTMSP[MDP], reacts with metal nitrates in methanol to form complexes M-2(DTMSP[MDP])(3) for M = Fe, Eu and Yb and M(DTMSP[MDP])(2) for M = Th. The sodium salt, Na-2(DTMSP[MDP]), forms upon neutralization of H2DTMSP[MDP] with NaOH, The calcium salt, Ca(DTMSP[MDP]), forms upon addition of the aqueous metal nitrate to an equivalent amount of the neutralized ligand in methanol. Elemental analysis, infrared spectroscopy and magnetic susceptibility measurements were used to characterize the compounds. Frequency shifts in the asymmetric and symmetric POO- stretching bands of the Fe, Eu, Yb and Th compounds indicate symmetrical coordination of the phosphonate groups through chelate and/or bridging interactions. The frequency difference between these stretching bands becomes smaller as the ionic potential (e/r) of the metal ion increases.

  DOI：

  10.1081/sim-120003208
• 作为产物：
  描述：

  methylenebis(3-(trimethylsilyl)propyl methyl phosphonate) 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以95%的产率得到methylenebisphosphonic acid P,P'-di[3-(trimethylsilyl)propyl] diester
  参考文献：
  名称：

  Facile high yielding synthesis of symmetric esters of methylenebisphosphonic acid

  摘要：

  The 1H-tetrazole catalyzed coupling of methylenebis(phosphonic dichloride), CH2(POCl2)(2), with primary alkyl, cyclic secondary alkyl, aromatic, and silicon- and fluorine-containing alcohols selectively affords symmetric P,P'-dialkyl partial esters as wen as homoleptic and mixed tetraesters. Two partial ester intermediates, methylenebis(2-ethylhexyl phosphonic chloride) and 2-ethylhexyl methylenebisphosphonic trichloride, were observed by H-1- and P-31 NMR spectroscopy in the esterification of CH2(POCl2)(2) with 2-ethyl-1-hexanol. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00846-8

文献信息

• Synthesis and Characterization of Di-[3-(Trimethylsilyl)-1-Propylene] Alkylenediphosphonic Acids
  作者：Julie A. Griffith-dzielawa、Richard E. Barrans、Daniel R. Mcalister、Mark L. Dietz、Albert W. Herlinger

  DOI：10.1080/00397910008087391

  日期：2000.1

  acids was successfully esterified with 3-(trimethylsilyl)-1-propanol to the symmetrically-substituted diesters. The procedure, which has general applicability for incorporating silicon heteroatoms into diphosphonic acids, utilizes the esterification reagent dicyclohexyl-carbodiimide (DCC) to activate the acid. The aggregation properties of the di-[3-(trimethylsilyl)-1-propylene] alkylenediphosphonic acids

  摘要 一个同源系列的亚烷基二膦酸与 3-(三甲基甲硅烷基)-1-丙醇成功酯化成对称取代的二酯。该方法具有将硅杂原子结合到二膦酸中的普遍适用性，利用酯化试剂二环己基碳二亚胺 (DCC) 来激活酸。在甲苯和1-癸醇中测量二-[3-(三甲基甲硅烷基)-1-丙烯]亚烷基二膦酸的聚集特性。
• A FACILE AND SELECTIVE HIGH YIELD SYNTHESIS OF SYMMETRIC DIALKYL-SUBSTITUTED METHYLENEBISPHOSPHONIC ACIDS
  作者：Dominique C. Stepinski、Albert W. Herlinger

  DOI：10.1081/scc-120006033

  日期：2002.1

  ABSTRACT Symmetric P,P′-dialkyl partial esters of methylenebisphosphonic acid were prepared in high yield and high selectivity from the corresponding acid chloride via a facile two-step, one-pot process. The newly developed synthesis, which does not require chromatographic or acid–base extractive purification, offers substantial advantages over previously used procedures.

  摘要 通过简便的两步一锅法从相应的酰氯以高收率和高选择性制备亚甲基双膦酸的对称 P,P'-二烷基偏酯。新开发的合成不需要色谱或酸碱萃取纯化，与以前使用的程序相比具有很大的优势。
• Synthesis of Symmetrical Methylenebis(Alkyl Hydrogen Phosphonates) by Selective Cleavage of Methylenebis(Dialkyl Phosphonates) with Morpholine
  作者：Gantla Vidyasagar Reddy、Hollie K. Jacobs、Aravamudan S. Gopalan、Richard E. Barrans、Mark L. Dietz、Dominique C. Stepinski、Albert W. Herlinger

  DOI：10.1081/scc-120027271

  日期：2004.1

  c acids has been of recent interest due to their potential therapeutic applications. This paper describes a convenient method to prepare symmetrical methylenebis(alkyl hydrogen phosphonates) by the selective cleavage of the corresponding methylenebis(dialkyl phosphonate) with refluxing morpholine. The effects of structural variations on the amine as well as the substrate have been investigated to understand

  摘要 由于其潜在的治疗应用，亚甲基双膦酸偏酯的制备最近引起了人们的兴趣。本文描述了一种通过用回流的吗啉选择性裂解相应的亚甲基双（二烷基膦酸）来制备对称亚甲基双（烷基氢膦酸）的简便方法。已经研究了结构变化对胺和底物的影响，以了解该反应的范围和局限性。受阻双膦酸酯的一种更好的方法是使用吗啉裂解它们的二甲酯 4。该方法也可用于获取许多 C-烷基二烷基亚甲基双膦酸，例如 6。该研究清楚地表明，用吗啉裂解方便、便宜、