1,4-diaminobutane-N,N,N',N'-tetrakis(methanephosphonic acid) | 56399-18-9

• 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: 1,4-diaminobutane-N,N,N',N'-tetrakis(methanephosphonic acid)
• 英文别名: tetramethylenediamine tetra(methylenephosphonic acid)；N,N,N',N'-tetramethylenephosphono-1,4-diaminobutane；butylene diamine tetra(methylene phosphonic acid)；tetramethylenediaminotetra(methylphosphonic) acid；N,N,N',N'-tetramethylphosphono-1,4-diaminobutane；H₈BDTMP；[4-[Bis(phosphonomethyl)amino]butyl-(phosphonomethyl)amino]methylphosphonic acid
• CAS: 56399-18-9
• 化学式: C₈H₂₄N₂O₁₂P₄
• 分子量: 464.18
• InChiKey: LAFFXEBYYYOEJX-UHFFFAOYSA-N

物化性质

• 熔点：
  240 °C
• 沸点：
  879.5±75.0 °C(Predicted)
• 密度：
  1.843±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -10.5
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  237
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  gadolinium(III) oxide 、 1,4-diaminobutane-N,N,N',N'-tetrakis(methanephosphonic acid) 在 sodium hydroxide 作用下， 以 水 为溶剂， 以94%的产率得到
  参考文献：
  名称：

  Synthesis, characterization and comparative study of aminophosphonate chelates of gadolinium(III) ions as magnetic resonance imaging contrast agents

  摘要：

  Gadolinium(III) complexes of aminophosphonates, including a novel ligand LH-4(8), have been investigated as potential contrast agents for NMR imaging. Water H-1 relaxivities at 10 and 200 MHz were determined and luminescence measurements, on Tb(III) complexes, allowed the determination of the number of coordinated H2O molecules. The complexes bound strongly to hydroxyapatite, suggesting possible targetting to bone in vivo. This was confirmed by Gd-153 tracer studies with the most favourable biodistribution in rats being shown by gadolinium(III) ethylenediamine-N,N,N',N'-tetrakis(methylenephosphonate).

  DOI：

  10.1016/0277-5387(94)80018-9
• 作为产物：
  描述：

  聚合甲醛 、 四亚甲基二胺 在 盐酸 、 亚磷酸 作用下， 以 水 为溶剂， 反应 3.5h， 生成 1,4-diaminobutane-N,N,N',N'-tetrakis(methanephosphonic acid)
  参考文献：
  名称：

  新膦酸的合成、晶体结构、胆碱酯酶抑制活性、杀虫活性评估和计算研究

  摘要：

  摘要 为了获得对人体毒性低的改良新型杀虫剂，设计了一系列新型单膦酸、双膦酸和四膦酸衍生物，并对其进行红外、1 H、13 C和31表征。P NMR光谱和X射线晶体学。使用体外 Ellman 方法评估合成化合物对人和昆虫乙酰胆碱酯酶 (AChE) 的抑制作用。选择其中一些具有低人类毒性和高昆虫毒性的化合物来评估（体内）对榆叶甲虫（X. luteola）第三龄幼虫的杀灭作用。体内和体外证据表明，含有疏水系统的双膦酸对昆虫 AChE 抑制具有良好的选择性。在本研究中，对接结果表明，与四膦酸相比，双膦酸具有较低的结合能和较高的抑制作用，这是由于其拓扑结构的类型及其氢与催化三联体（酶的主要活性位点）相互作用的能力。 . 此外，QSAR结果表明，影响目标化合物杀虫活性的主要因素是疏水性、大小、形状和形成氢键的能力。本研究有助于开发新的杀虫剂。 图形摘要

  DOI：

  10.1007/s11030-021-10283-7

文献信息

• Aromatic Chelator-Specific Lattice Architecture and Dimensionality in Binary and Ternary Cu(II)-Organophosphonate Materials
  作者：V. Georgantas、M. Menelaou、V. Psycharis、C. P. Raptopoulou、A. Terzis、V. Tangoulis、C. Mateescu、A. Salifoglou

  DOI：10.1021/ic302598d

  日期：2013.5.6

  binder on the chemical reactivity in binary and ternary systems of Cu(II) in aqueous and nonaqueous media and (b) denote the correlation of ligand hydrophilicity, aromaticity, denticity, charge, and H-bonding interactions with emerging defined Cu(II)–H8BDTMP structures of distinct lattice identity and spectroscopic-magnetic properties. Collectively, such structural and chemical factors formulate the

  与丁二胺四（亚甲基膦酸）（H 8 BDTMP）和杂环有机螯合剂（吡啶和1,10-菲咯啉）的Cu（II）二元/三元体系中定义的晶格尺寸和结构材料的设计相关的合成工作）导致分离出新的有机膦酸铜化合物，即Na 6 [Cu 2（BDTMP）（H 2 O）4 ]·[Cu 2（BDTMP）（H 2 O）4 ] 0.5 ·26H 2 O（1） ，[Cu 2（H 4 BDTMP）（py）4 ]·2H 2 O（2）和[Cu 2（H 4 BDTMP）（phen）2 ] n ·6.6 n H 2 O·1.5 n MeOH（3）。1 - 3是从铜（II）-BDTMP物种的家庭中分离的第1化合物。它们的特征在于元素分析，光谱技术（FT-IR，UV-vis），磁化率，TGA-DTG，循环伏安法和X射线晶体学。1中的晶格揭示了存在于离散的双核Cu（II）单元的存在，该单元与BDTMP 8–和方形金字塔几何形状的水分子结
• The Direct Synthesis of α-Aminomethylphosphonic Acids. Mannich-Type Reactions with Orthophosphorous Acid
  作者：Kurt Moedritzer、Riyad R. Irani

  DOI：10.1021/jo01343a067

  日期：1966.5
• Green Synthesis of Poly(aminomethylenephosphonic) Acids
  作者：Didier Villemin、Bernard Moreau、Abdelghani Elbilali、Mohamed-Amine Didi、M’hamed Kaid、Paul-Alain Jaffrès

  DOI：10.1080/10426501003724897

  日期：2010.11.23

  The reaction of polyamines with phosphorous acid and formaldehyde in water under focused microwave irradiation provides a facile and rapid synthesis of poly(aminomethylenephosphonic) acids.
• Synthesis, crystal structure and fluorescent characterization of a novel lanthanide tetraphosphonate with a layered structure
  作者：Shao-Ming Ying、Xi-Rui Zeng、Xiao-Niu Fang、Xin-Fa Li、Dong-sheng Liu

  DOI：10.1016/j.ica.2005.12.023

  日期：2006.3

  Hydrothermal reactions of Gd(III) nitrate with N,N,N',N'-tetramethylenephosphono-1,4-diaminobutane, (H2O3PCH2)(2)N-(CH2)(4)-N(CH2PO3H2)(2) (H8L), afforded a novel Gd(III) phosphonate, namely, Gd[(O3PCH2)(HO3PCH2)N(H)(CH2)(4)N(H)(CH2PO3H)(2)] center dot 2H(2)O, [Gd(H5L)] center dot 2H(2)O. Its structure was established by a single-crystal X-ray diffraction study. In this compound, the the Gd(III) ion is coordinated by eight phoshonate oxygen atoms from five different phosphonate groups, which belong to five different phosphonic ligands. Each Gd atom is connected with its neighboring Gd atoms by two phosphonate oxygens, forming a gadolinium phosphonate slab along the a-axis. Such slabs are bridged by tetraphosphonate H5L anions, resulting in a 0 1 1 layer with the butane groups toward the interlayer space. These layers are further interlinked by strong hydrogen bonds formed by uncoordinated phosphonate oxygens into a 3D supermolecular structure. Luminescent studies indicate that this compound exhibits a broad blue fluorescent emission band at 441 nm. (c) 2005 Elsevier B.V. All rights reserved.
• Inorganic–organic hybrid compounds: hydrothermal synthesis and characterization of a new three-dimensional metal tetraphosphonate Mn[(HO3PCH2)N(H)(CH2)4(H)N(CH2PO3H)2]
  作者：Norbert Stock、Max Rauscher、Thomas Bein

  DOI：10.1016/j.jssc.2003.08.005

  日期：2004.3

  The new manganese tetraphosphonate. Mn[(HO3PCH2)(2)N(H)(CH2)(4)(H)N(CH2PO3)(2)] (1) was hydrothermally synthesized from MnCl2 and N,N,N',N'-tetrametylphospliono-1,4-diaminobutane, (H2O3PCH2)(2)N-(CH2)(4)-N(CH2PO3H2)(2). The structure was determined from single-crystal X-ray diffraction data (Mn[(HO3PCH2)(2)N(H)(CH2)(4)(H)N(CH2PO3)(2)], monoclinic, P2(1)/a, with a = 9.6663(1), b = 9.2249(2), c = 10.5452(1) pin, beta = 105.676(1)degrees, V = 905.35(3) x 10(6) pm, Z = 2, R-1 = 0.051, wR(2) = 0.109 (all data). The structure contains the zwitter ions [(HO3PCH2)(2)N(H)-(CH2)(4)-(H)N(CH2PO3)(2)](2-) and is built from alternating corner-linked [MnO6] and [PO3C] polyhedra forming a two-dimensional net of eight-rings. These layers are connected to a pillared structure by the diaminobutane groups. Magnetic susceptibility data confirms the presence of Mn2+ ions. Thermogravimetric measurements show a stability of 1 up to similar to 290degreesC. Between 290degreesC and 345degreesC a one-step loss of similar to 7.0% is observed, and above 345degreesC the continuous decomposition of the organic part of the structures takes place. (C) 2003 Elsevier Inc. All rights reserved.