[(2-bromoacetylamino)methyl]phosphonic acid diethyl ester | 95397-85-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: [(2-bromoacetylamino)methyl]phosphonic acid diethyl ester
• 英文别名: diethyl bromoacetamidomethylphosphonate；2-bromo-N-(diethoxyphosphorylmethyl)acetamide
• CAS: 95397-85-6
• 化学式: C₇H₁₅BrNO₄P
• 分子量: 288.078
• InChiKey: XDKIOFKUUCDKNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  、 [(2-bromoacetylamino)methyl]phosphonic acid diethyl ester 在 N,N-二异丙基乙胺 作用下， 以 氯仿 为溶剂， 以48 %的产率得到
  参考文献：
  名称：

  具有 (3-聚氨基) 菲咯啉配体的钌 (II) 配合物的分子工程用于开发可重复使用的铜 (II) 离子光学传感器

  摘要：

  这项工作旨在开发基于带有膦酸盐锚定基团的化学传感器的发光杂化有机-无机材料的合成方法，用于检测水溶液中的有毒金属离子。为此，研究了膦酸盐取代的钌( II )配合物与(3-聚氨基)菲咯啉Ru(N 3 P 3 phen)在生理pH下对水介质中有毒金属离子的传感特性，并与已知的那些进行了比较。用于铜( II )离子的选择性化学传感器Ru(N 2 P 2 phen) 。Ru ( N 3 P 3 phen)复合物使我们能够通过发光测量来检测铜 ( II )，并且比Ru(N 2 P 2 phen) 更灵敏（检测限 (LOD) 为 0.02 μM）。本文研究的化学传感器Ru(N 2 P 2 phen)和Ru(N 3 P 3 phen)的主要优点是可以将它们固定在氧化钛表面上，而无需使用膦酸酯取代基作为锚定基团的额外合成成本。经 TMSBr 活化后，两种配合物均成功接枝到水合介孔 TiO 2 ( S BET

  DOI：

  10.1039/d2tc03764e
• 作为产物：
  描述：

  diethyl N-benzylaminomethylphosphonate 在 10percent Pd/C sodium hydroxide 、 甲酸铵 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(2-bromoacetylamino)methyl]phosphonic acid diethyl ester
  参考文献：
  名称：

  Non-covalent Conjugates between Cationic Polyamino Acids and GdIII Chelates: A Route for Seeking Accumulation of MRI-Contrast Agents at Tumor Targeting Sites

  摘要：

  Three novel Gd chelates containing on their external surface pendant phosphonate and carboxylate groups, which promote the interaction with the positively charged groups of polyornithine and polyarginine, have been synthesized. Their solution structures have been assessed on the basis of H-1- and P-31-NMR spectra of the Eu and Yb analogues. A thorough investigation of the relaxometric (H-1 and O-17) Properties of the Gd chelates has been carried out and the observed relaxivities have been accounted for the sum of three contributions arising from water molecules in the first, second, and outer coordination layers, respectively. It has been found that the occurrence of a tight second coordination coating renders the dissociation of the water molecule directly coordinated to the Gd ion more difficult. The binding interactions between the negatively charged Gd chelates and the positively charged groups of polyornithine (ca. 140 residues) and polyarginine (ca. 204 residues) have been evaluated by means of the proton relaxation enhancement (PRE) method. Although the binding interaction decreases markedly in the presence of competitive anions in the solution medium, the affinity is strong enough that in blood serum it is possible to meet the conditions where most of the chelate is bound to the polyamino acid substrate. On this basis one may envisage a novel route for a MRI location of tumors as it is known that positively charged polyamino acids selectively bind to tumors having a greater negative charge than non-tumor cells.

  DOI：

  10.1002/1521-3765(20000717)6:14<2609::aid-chem2609>3.0.co;2-s

文献信息

• pH sensitive MRI contrast agents
  申请人：Board of Regents the University of Texas System

  公开号：US06746662B1

  公开（公告）日：2004-06-08

  A composition and method is disclosed for providing a magnetic resonance imaging contrast agent that is sensitive to pH, the compound and salts thereof including, a tetraaza base having a spacer at each of the amide groups, and a proton exchange attached to each of the spacer molecules, wherein the proton exchange group groups mediate proton exchange with water molecules that are trapped within the tetraaza base molecule.

  本发明揭示了一种用于提供对pH敏感的磁共振成像造影剂的组合物和方法，其包括具有在每个酰胺基团上的间隔子的四氮杂基和其盐，以及连接到每个间隔子分子上的质子交换基团，其中质子交换基团介导与被困在四氮杂基分子内的水分子的质子交换。
• Modulation of the Lifetime of Water Bound to Lanthanide Metal Ions in Complexes with Ligands Derived from 1,4,7,10-Tetraazacyclododecane Tetraacetate (DOTA)
  作者：Shanrong Zhang、Xiuyan Jiang、A. Dean Sherry

  DOI：10.1002/hlca.200590086

  日期：2005.5

  tetraamide derivatives of DOTA were synthesized, and their lanthanide(III) complexes were examined by multinuclear 1H-, 13C-, and 17O-NMR spectroscopy, and compared with literature data of similar, known complexes (Table). All ligands formed structures similar to the parent [LnIII(DOTA)]− complexes, with four N-atoms and four O-atoms from DOTA and one O-atom from the inner-sphere water molecules. Interestingly

  合成了一系列DOTA的二酰胺和四酰胺衍生物，并通过多核1 H-，13 C-和17 O-NMR光谱检查了它们的镧系元素（III）配合物，并与相似的已知配合物的文献数据进行了比较（表）。所有配体形成类似于母体[Ln III（DOTA）] -配合物的结构，其中DOTA带有四个N原子和四个O原子，内圈水分子带有一个O原子。有趣的是，寿命τ中号的内球面的，金属结合的水分子广泛地变化，范围从纳米到毫秒，这取决于悬垂酰胺侧链的身份。通常，带正电的[LnIII（DOTA-四酰胺）] 3+络合物显示最长的停留时间（高τ中号的值），而在扩展酰胺与另外的带电官能团的复合物显示小得多的τ中号值，即使当侧基不直接协调，以中心的Ln 3+离子。新颖的设计[LN III（DOTA-四酰胺）] 3+配合物的宽，调谐范围τ中号值是最重要的用于快速响应的，顺磁性化学交换饱和转移（PARACEST）成像的应用用于研究生理和代谢过程的药物。
• Colorimetric Hg²⁺ Sensing in Water: From Molecules toward Low-Cost Solid Devices
  作者：Elizaveta Ermakova、Julien Michalak、Michel Meyer、Vladimir Arslanov、Aslan Tsivadze、Roger Guilard、Alla Bessmertnykh-Lemeune

  DOI：10.1021/ol303499v

  日期：2013.2.1

  colorimetric molecular sensor allowing for cheap, fast, sensitive, and highly selective naked-eye detection of Hg2+ in water is described. This molecule combines a 1,8-diaminoanthraquinone signaling subunit and phosphonic acid esters that confer the water solubility to the dye (R = H). A ready-to-use colorimetric solid sensor was obtained by incorporating an amphiphilic analog (R = OC12H25) exhibiting

  描述了一种新型的比色分子传感器，该传感器可对水中的Hg 2+进行便宜，快速，灵敏和高度选择性的肉眼检测。该分子结合了1,8-二氨基蒽醌信号传导亚基和膦酸酯，这些膦酸酯赋予染料以水溶性（R = H）。通过在琼脂糖膜中掺入表现出相似结合特性和光学响应的两亲性类似物（R = OC 12 H 25），即可获得比色固体传感器。
• 6-Polyamino-substituted quinolines: synthesis and multiple metal (Cu^II, Hg^IIand Zn^II) monitoring in aqueous media
  作者：Anton S. Abel、Alexei D. Averin、Andrey V. Cheprakov、Vitaly A. Roznyatovsky、Franck Denat、Alla Bessmertnykh-Lemeune、Irina P. Beletskaya

  DOI：10.1039/c9ob00259f

  日期：——

  Chemoselective palladium-catalyzed arylation of polyamines with 6-bromoquinoline has been explored to prepare chelators for the detection of metal cations in aqueous media. The introduction of a single aromatic moiety into non-protected polyamine molecules was achieved using the commercially available Pd(dba)2/BINAP precatalyst to afford nitrogen chelators, in which the aromatic signalling unit is

  已经探索了多胺的化学选择性钯催化的多胺芳基化反应，以制备用于检测水性介质中金属阳离子的螯合剂。使用市售的Pd（dba）2 / BINAP预催化剂可将单个芳香族部分引入未保护的多胺分子中，以提供氮螯合剂，其中芳香族信号单元直接连接至多胺残基。然后使用N合成水溶性受体这些多胺通过亲水配位残基进行-烷基化。通过在单个分子装置中结合6-氨基喹啉单元的丰富光物理特性与螯合多胺的高配位亲和力和羧酰胺基取代的膦酸二酯的亲水特性，我们合成了选择性双通道化学传感器5（UV-vis和荧光光谱）在生理水平下检测水性介质中的Cu II离子。该受体适用于饮用水分析和纸试纸的制造，用于在紫外光下肉眼检测Cu II离子。通过增加供体部位的数量，我们还获得了化学传感器6，该传感器可有效检测汞II离子。此外，化学传感器6还适用于金属离子的多次检测，因为它不仅螯合Hg II离子，而且还螯合在这三种阳离子存在下显示出不同发射响应的Cu
• Rational design of aminoanthraquinones for colorimetric detection of heavy metal ions in aqueous solution
  作者：Elena Ranyuk、Alexei Uglov、Michel Meyer、Alla Bessmertnykh Lemeune、Franck Denat、Alexei Averin、Irina Beletskaya、Roger Guilard

  DOI：10.1039/c1dt10677e

  日期：——

  prepared with the aim of assaying metal cations. The outstanding UV-Vis absorption properties of the 1-aminoanthraquinone chromophore allowed the efficient visual detection and quantification of copper(II) ions by chelatorsL1–L3 in buffered aqueous solution. Moreover, the visible response of L2 is not interfered by addition of large excesses of 13 common metal ions, whereas chemosensor L3 produces also

  为了测定金属阳离子，制备了一种水溶性比色化学传感器家族，其掺入了被带有多胺链的功能化的蒽醌信号亚基，该多胺链带有亲水性二乙氧基磷酰基部分。1-氨基蒽醌生色团具有出色的UV-Vis吸收特性，可通过螯合剂L 1 - L 3在缓冲水溶液中进行可视检测和定量铜（II）离子。此外，L 2的可见响应不会因添加大量过量的13种常见金属离子而受到干扰，而化学传感器L 3在等摩尔量的铅存在下也会产生颜色变化（II）。考虑到两个吸收最大值之间的134 nm间隙，可以设想同时比色定量测定铅和铜。详细电位和分光光度分析的Cu 2+络合大号2和大号3，以及铅2+和Cd 2+由大号3，以获得一个更深入的了解pH依赖性形态和理解了颜色变化被承担过程。此外，[Pb L 3 ] 2+配合物的内部配位球通过NMR光谱法探测。