(2,4-二硝基苯基)磷酸二氢酯 | 2566-26-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 中文名称: (2,4-二硝基苯基)磷酸二氢酯
• 英文名称: 2,4-dinitrophenyl dihydrogen phosphate
• 英文别名: 2,4-Dinitrophenylphosphat；2,4-dinitrophenyl phosphate；(2,4-Dinitrophenyl)-dihydrogenphosphat；2,4-DNPP；Mono-2,4-dinitrophenyl-phosphat；2,4-Dinitrophenol dihydrogen phosphate；(2,4-dinitrophenyl) dihydrogen phosphate
• CAS: 2566-26-9
• 化学式: C₆H₅N₂O₈P
• 分子量: 264.088
• InChiKey: OABKEGPGBFWYDX-UHFFFAOYSA-N

物化性质

• 沸点：
  521.9±60.0 °C(Predicted)
• 密度：
  1.889±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  158
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2,4-二硝基苯基)磷酸二氢酯 在 C₄₄H₅₄N₆Ni₂O₇*2ClHO₄ 、 水 、 lithium perchlorate 作用下， 以 乙腈 为溶剂， 生成 2,4-二硝基酚
  参考文献：
  名称：

  Three new dinuclear nickel(II) complexes with amine pendant-armed ligands: Characterization, DFT study, antibacterial and hydrolase-like activity

  摘要：

  Herein, we report the synthesis and characterization of three new Ni(II) complexes, namely: [Ni-2(H2LEt)(mu-OAc)(2)(H2O)]BPh4 center dot ClO4 (1), (H2LEt = 2-[(N-benzyl-N-2-pyridyl methylamine)]-4-methyl-6-[N-2(pyridylmethyl) aminomethyl)]-6((2-aminoethyl)amino)methyl phenol); [Ni-2(H(2)LProp)(mu-OAc)(2)(H2O)](ClO4)(2) (2), (H(2)LProp = 2-[(N-benzyl-N-2-pyridylmethylamine)]-4-methyl-6-[N-(2-pyridylmethyl)aminomethyl]-6-((2-aminopropyl) amino)methylphenol); and [Ni-2(LBut)(mu-OAc)(2)(H2O)](HCl)(2) (3), (LBut = 2-[(N-benzyl-N-2-pyridylmethylamine)]-4-methyl-6-[N-(2-pyridylmethyl)aminomethyl]-6-((2-aminobuthyl) amino)methylphenol). All of them were characterized through spectroscopic techniques (elemental analysis, IR, UV-Vis spectroscopy), ESI-MS, electrochemistry and potentiometric titration. Density functional theory (DFT) was used to better understand the electronic and molecular structure of these complexes. The hydrolytic activity of complexes 1-3 towards the 2,4-BDNPP substrate was analyzed and complex 2 presented the highest catalytic efficiency (k(cat)/K-M) of the three, possibly due to a greater interaction with the substrate. The complexes were also screened for their antibacterial activities using both Gram-positive and Gram-negative bacterial strains by minimum inhibitory concentration and minimum bactericidal concentration methods.

  DOI：

  10.1016/j.ica.2020.119559
• 作为产物：
  描述：

  2,4-二硝基酚 在 2,6-二甲基吡啶 、 氢溴酸 作用下， 以 乙醚 为溶剂， 生成 (2,4-二硝基苯基)磷酸二氢酯
  参考文献：
  名称：

  The Reactivity of Phosphate Esters. Monoester Hydrolysis

  摘要：

  DOI：

  10.1021/ja00978a044
• 作为试剂：
  描述：

  苯酚 在 (2,4-二硝基苯基)磷酸二氢酯 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 phenyl monophosphate
  参考文献：
  名称：

  Reactions of the monomeric metaphosphate anion generated from different sources

  摘要：

  DOI：

  10.1021/ja00369a033

文献信息

• Cu(<scp>ii</scp>) complexes with tridentate sulfur and selenium ligands: catecholase and hydrolysis activity
  作者：Daniele Cocco Durigon、Marcos Maragno Peterle、Adailton João Bortoluzzi、Ronny Rocha Ribeiro、Antonio Luiz Braga、Rosely Aparecida Peralta、Ademir Neves

  DOI：10.1039/d0nj02806a

  日期：——

  Two new copper(ii) mononuclear complexes (CSe and CS) were synthesized and characterized by the following techniques: X-ray crystallography, elemental analysis, IR, EPR and UV-vis spectroscopies, conductimetric analysis and mass spectrometry.

  两种新的铜（II）单核配合物（CSe和CS）通过以下技术合成并表征：X射线晶体学、元素分析、红外、电子顺磁共振和紫外-可见光谱、电导率分析和质谱。
• Synthesis and enhanced DNA cleavage activities of bis-tacnorthoamide derivatives
  作者：Li Wei、Ying Shao、Mi Zhou、Hong-Wen Hu、Guo-Yuan Lu

  DOI：10.1039/c2ob25743b

  日期：——

  A new metal-free DNA cleaving reagent, bis-tacnorthoamide derivative 1 with two tacnorthoamide (tacnoa) units linked by a spacer containing anthraquinone, has been synthesized from triazatricyclo[5.2.1.04,10]decane and characterized by NMR and mass spectrometry. For comparison, the corresponding compounds mono-tacnorthoamide derivative 2 with one tacnorthoamide unit and 6 with two tacnorthoamide units linked by an alkyl (1,6-hexamethylene) spacer without anthraquinone have also been synthesized. The DNA-binding property investigated via fluorescence and CD spectroscopy suggests that compounds 1 and 2 have an intercalating DNA binding mode, and the apparent binding constants of 1, 2 and 6 are 1.3 × 107 M−1, 0.8 × 107 M−1 and 8 × 105 M−1, respectively. Agarose gel electrophoresis was used to assess plasmid pUC19 DNA cleavage activity promoted by 1, 2, 6 and parent tacnoa under physiological conditions, which gives rate constants kobs of 0.2126 ± 0.0055 h−1, 0.0620 ± 0.0024 h−1, 0.040 ± 0.0007 h−1 and 0.0043 ± 0.0002 h−1, respectively. The 50-fold and 15-fold rate acceleration over parent tacnoa is because of the anthraquinone moiety of compound 1 or 2 intercalating into DNA base pairs via a stacking interaction. Moreover, DNA cleavage reactions promoted by compound 1 give 5.3-fold rate acceleration over compound 6, which further demonstrates that the introduction of anthraquinone results in a large enhancement of DNA cleavage activity. In particular, DNA cleavage activity promoted by 1 bearing two tacnoa units is 3.3 times more effective than 2 bearing one tacnoa unit and the DNA cleavage by compound 1 was achieved effectively at a relatively low concentration (0.03 mM). This dramatic rate acceleration suggests the cooperative catalysis of the two positively charged tacnoa units in compound 1. The radical scavenger inhibition study and ESI-MS analysis of bis(2,4-dinitrophenyl) phosphate (BDNPP) and adenylyl(3′-5′)phosphoadenine (APA) cleavage in the presence of compound 1 suggest the cleavage mechanism would be via a hydrolysis pathway by cleaving the phosphodiester bond of DNA.

  一种新型无金属DNA切割试剂，即由包含蒽醌的间隔基连接的两个tacnoa（tacnorthoamide）单元的双tacnoa衍生物1，已从三氮杂三环[5.2.1.04,10]癸烷合成并由NMR和质谱进行表征。为了比较，还合成了相应的单tacnoa衍生物2（含有一个tacnoa单元）和6（含有两个tacnoa单元，通过不含蒽醌的烷基（1,6-己二基）间隔基连接）。通过荧光和圆二色光谱调查的DNA结合性质表明，化合物1和2具有插入式DNA结合模式，其表观结合常数分别为1.3 × 10^7 M^-1、0.8 × 10^7 M^-1和8 × 10^5 M^-1。使用琼脂糖凝胶电泳评估在生理条件下由1、2、6和母体tacnoa促进的质粒pUC19 DNA切割活性，分别得到速率常数kobs为0.2126 ± 0.0055 h^-1、0.0620 ± 0.0024 h^-1、0.040 ± 0.0007 h^-1和0.0043 ± 0.0002 h^-1。相比于母体tacnoa，速率分别提高了50倍和15倍，这是由于化合物1或2的蒽醌部分通过堆叠相互作用插入到DNA碱基对中。此外，由化合物1促进的DNA切割反应的速率比化合物6提高了5.3倍，进一步证明蒽醌的引入大大增强了DNA切割活性。特别是，具有两个tacnoa单元的1促进的DNA切割活性比具有一个tacnoa单元的2高出3.3倍，并且在相对较低的浓度（0.03 mM）下有效实现了化合物1的DNA切割。这种显著的速率加速表明化合物1中的两个正电荷tacnoa单元之间的协同催化作用。自由基清除剂抑制研究和ESI-MS分析显示，在化合物1存在下，双（2,4-二硝基苯基）磷酸（BDNPP）和腺苷(3′-5′)磷酸腺苷（APA）的切割表明切割机制是通过水解途径切割DNA的磷酸二酯键。
• Unsymmetrical dizinc complexes as models for the active sites of phosphohydrolases
  作者：Martin Jarenmark、Edit Csapó、Jyoti Singh、Simone Wöckel、Etelka Farkas、Franc Meyer、Matti Haukka、Ebbe Nordlander

  DOI：10.1039/b925563j

  日期：——

  complexes, [Zn2(IPCPMP)(OAc)}2][PF6]2 (2) and [Zn2(IPCPMP)(Piv)}2][PF6]2 (3) (OAc = acetate; Piv = pivalate). The crystal structures of 2 and 3 show that they consist of tetranuclear complexes with very similar structures. Infrared spectroscopy and mass spectrometry indicate that the tetranuclear complexes dissociate into dinuclear complexes in solution. Potentiometric studies of the Zn(II) : IPCPMP system

  不对称双核配体 2-（N-异丙基-N -（（（2-吡啶基）甲基）氨基甲基）-6-（N-（羧甲基）-N -（（2-吡啶基）甲基）氨基甲基）-4-甲基苯酚 （IPCP文件或L）已被合成以模拟双核金属水解酶的活性位点环境。它已被分离为六氟磷酸盐H 4 IPCPMP（PF 6）2 ·2H 2 O（H 4 L），已在结构上进行了表征，并已用于形成两种不同的锌（II）配合物[Zn 2（IPCPMP）（OAc）} 2 ] [PF 6 ] 2（2）和[Zn 2（IPCPMP）（Piv）} 2 ] [PF 6 ] 2（3）（OAc =醋酸盐; Piv =新奇的）。2和3的晶体结构表明它们由具有非常相似结构的四核配合物组成。红外光谱和质谱表明，四核复合物在溶液中解离成双核复合物。Zn（II）的电位研究： IPCP文件 水溶液体系显示单核配合物即使在2：1的低pH条件下也出奇地稳定 锌（II） ：L比，但在
• Selectivity of monomeric metaphosphate reactions with alcohols in polar aprotic solvents
  作者：Fausto Ramirex、James F Marecek、Shrishailam S. Yemul

  DOI：10.1016/s0040-4039(00)87146-4

  日期：1982.1

  Evidence is presented for selectivity in the reaction of metaphosphate, PO3−, with methanol in preference to t-butanol in acetonitrile solution. In dichloromethane solution there is also evidence for preferential nucleophilic solvation of reactant by methanol vs. t-butanol.

  证据提出了一种用于在偏的反应选择性，PO 3 - ，用甲醇优先于叔丁醇中的乙腈溶液。在二氯甲烷溶液中，也有证据表明甲醇相对于叔丁醇对反应物具有优先的亲核溶剂化作用。
• Synthesis, characterization, hydrolase and catecholase activity of a dinuclear iron(III) complex: Catalytic promiscuity
  作者：Tiago P. Camargo、Fernanda F. Maia、Cláudia Chaves、Bernardo de Souza、Adailton J. Bortoluzzi、Nathalia Castilho、Tiago Bortolotto、Hernán Terenzi、Eduardo E. Castellano、Wolfgang Haase、Zbigniew Tomkowicz、Rosely A. Peralta、Ademir Neves

  DOI：10.1016/j.jinorgbio.2015.02.017

  日期：2015.5

  di-iron(III) complex [(bbpmp)(H2O)(Cl)FeIII(μ-Ophenoxo)FeIII(H2O)Cl)]Cl (1), with the symmetrical ligand 2,6-bis[(2-hydroxybenzyl)(pyridin-2-yl)methylamino]methyl}-4-methylphenol (H3bbpmp). Complexes 2 with the unsymmetrical ligand H2bpbpmp — 2-[[(2-hydroxybenzyl)(2-pyridylmethyl)]aminomethyl]-6-bis(pyridylmethyl) aminomethyl}-4-methylphenol and 3 with the ligand L1 = 4,11-dimethyl-1,8-bis2-[N-(di

  在此，我们报道了新型二铁（III）配合物[（bbpmp）（H 2 O）（Cl）Fe III（μ- O phenoxo）Fe III（H 2 O）Cl）] Cl（1），具有对称的配体2,6-双[（（2-羟基苄基）（吡啶-2-基）甲基氨基]甲基} -4-甲基苯酚（H 3 bbpmp）。配合物2与不对称配体H 2 bpbpmp — 2-[[（（2-羟基苄基）（2-吡啶基甲基）]氨基甲基] -6-双（吡啶基甲基）氨基甲基} -4-甲基苯酚和3与配体L 1 为了比较，包括＝ 4，11-二甲基-1，8-双2- [N-（二-2-吡啶基甲基）氨基]乙基}环酰胺。通过元素分析，X射线晶体学，磁化学，电子光谱，电化学，质谱和电位滴定对复合物1进行了表征。磁数据表明，双核配合物1的两个铁心之间的反铁磁耦合非常弱（J  =-0.29 cm -1）。由于两个铁中心均存在不稳定的配位位点，因此对二酯模型底物2,