苯酚,2,4-二硝基-,磷酸(酯)氢 | 18962-97-5

• 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: 苯酚,2,4-二硝基-,磷酸(酯)氢
• 英文名称: bis(2,4-dinitrophenyl)phosphate
• 英文别名: BDNPP；2,4-BDNPP；Bis-(2,4-dinitrophenyl)-phosphat；bis(2,4-dinitrophenyl) hydrogenphosphate；bis(2,4-dinitrophenol)phosphate；Bis(2,4-dinitrophenyl) phosphate；bis(2,4-dinitrophenyl) hydrogen phosphate
• CAS: 18962-97-5
• 化学式: C₁₂H₇N₄O₁₂P
• 分子量: 430.181
• InChiKey: QUTUMPWTNFFUNH-UHFFFAOYSA-N

物化性质

• 沸点：
  648.5±65.0 °C(Predicted)
• 密度：
  1.835±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  239
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  苯酚,2,4-二硝基-,磷酸(酯)氢 在 sodium nitrate 、 C₁₇H₃₉N₇*2Cu⁽²⁺⁾*4NO₃^(1-) 、 水 作用下， 生成 2,4-二硝基酚
  参考文献：
  名称：

  新型不对称双核铜配合物介导的磷酸酯水解

  摘要：

  E-mail: [e-mail] January 27, 2012 Accepted February 29, 2012Key Words : 不对称双核Cu(II)配合物、BDNPP、HPNPP、水解在开发携带两个或两个或多个的高效催化剂方面已经进行了大量的研究工作三种金属离子用于磷酸酯的水解。

  DOI：

  10.5012/bkcs.2012.33.6.2037

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。
• Bis(2,4-dinitrophenyl) phosphate hydrolysis mediated by lanthanide ions
  作者：Elisane Longhinotti、Josiel B. Domingos、Pedro L. F. da Silva、Bruno Szpoganicz、Faruk Nome

  DOI：10.1002/poc.868

  日期：2005.2

  The kinetics of the hydrolysis of bis(2,4-dinitrophenyl) phosphate (BDNPP) were studied in basic solutions in the presence of La3+, Sm3+, Tb3+ and Er3+. Bis-Tris propane (BTP) buffer was used to stabilize the Ln3+ hydroxide complexes in solution. Two equivalents of the 2,4-dinitrophenolate ion (DNP) were liberated for each equivalent of BDNPP and the reaction showed first-order kinetics. Potentiometric

  在碱性溶液中，在La 3+，Sm 3+，Tb 3+和Er 3+的存在下，研究了磷酸双（2,4-二硝基苯基）酯（BDNPP）的水解动力学。使用Bis-Tris丙烷（BTP）缓冲液来稳定溶液中的Ln 3+氢氧化物络合物。对于每当量的BDNPP，释放出两当量的2，4-二硝基苯酚离子（DNP），并且该反应显示出一级动力学。电位滴定表明形成了双核络合物，例如[Ln 2（BTP）2（OH）n ] （6- n），其值为n对于所有研究的金属，其随pH的变化而变化。因此，催化作用取决于具有几个羟基配体的双核镧系离子络合物的形成。版权所有©2004 John Wiley＆Sons，Ltd.
• Selective Hydrolysis of 4-Nitrophenyl Phosphate by a Dinuclear Cu(II) Complex
  作者：Jung Hee Kim

  DOI：10.1246/cl.2000.156

  日期：2000.2

  A flexible dinuclear Cu(II) complex with 1,3-bis(1,4,7-triaza-1-cyclononyl)propane, hydrolyzes 4-nitrophenyl phosphate under mild conditions, with 300 times rate enhancement over the corresponding mononuclear Cu(II) complex. In contrast, there is no difference in the reactivity in hydrolyzing bis(4-nitrophenyl)phosphate.

  一种由1,3-双(1,4,7-三氮杂-1-环壬基)丙烷构成的柔性双核铜(II)配合物，在温和条件下可水解4-硝基苯基磷酸酯，其速率比相应单核铜(II)配合物提高了300倍。相比之下，在水解双(4-硝基苯基)磷酸酯的反应活性方面没有差异。
• Phosphodiester hydrolysis promoted by dinuclear iron(III) complexes
  作者：Clovis Piovezan、Fábio da Silva Lisboa、Fábio Souza Nunes、Sueli Maria Drechsel

  DOI：10.1007/s11243-010-9437-z

  日期：2011.2

  compounds, namely [Fe2(bbppnol)(μ-AcO)(H2O)2](ClO4)2 (1), [Fe2(bbppnol)(μ-AcO)2](PF6) (2), and [Fe2(bbppnol)(μ-OH)(Cl)2]·6H2O (3), where H3bbppnol = N,N′-bis(2-hydroxybenzyl)-N,N′-bis(2-methylpyridyl)–1,3-propanediamine-2-ol, toward the hydrolysis of bis-(2,4-dinitrophenyl)phosphate as models for phosphoesterase activity. The synthesis and characterization of the new complexes 1 and 3 was also described

  我们报告了三种双核非血红素 Fe(III) 化合物的反应性，即 [Fe2(bbppnol)(μ-AcO)(H2O)2](ClO4)2 (1)、[Fe2(bbppnol)(μ-AcO) 2](PF6) (2) 和 [Fe2(bbppnol)(μ-OH)(Cl)2]·6H2O (3)，其中 H3bbppnol = N,N'-双(2-羟基苄基)-N,N' -bis(2-methylpyridyl)–1,3-propanediamine-2-ol，以双-(2,4-二硝基苯基)磷酸酯水解为磷酸酯酶活性模型。还描述了新配合物 1 和 3 的合成和表征。对这些复合物观察到的反应性差异表明，底物对反应位点的可及性是决定水解效率的关键步骤之一。
• 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。