tris(m-nitrophenyl) phosphate | 3862-04-2

• 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
• 英文名称: tris(m-nitrophenyl) phosphate
• 英文别名: tris(3-nitrophenyl)phosphate；Tris-3-nitrophenylphosphat；beta-Nitrophenylphosphate；tris(3-nitrophenyl) phosphate
• CAS: 3862-04-2
• 化学式: C₁₈H₁₂N₃O₁₀P
• 分子量: 461.281
• InChiKey: AIJAJGQAPNYWOW-UHFFFAOYSA-N

物化性质

• 沸点：
  553.7±45.0 °C(Predicted)
• 密度：
  1.572±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  182
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tris(m-nitrophenyl) phosphate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 bis(m-nitrophenyl) hydrogen phosphate
  参考文献：
  名称：

  磷酸酯的反应性。二酯水解

  摘要：

  磷酸二酯通常是极不反应的化合物，但它们对水解的反应性在很大程度上取决于离去基团的碱性。结果，随着离去基团的碱性降低，二酯和单酯单阴离子之间的反应性差异迅速减小，并且对于非常好的离去基团，两类化合物的反应性相当。磷酸二酯阴离子的水解机理似乎涉及溶剂对磷的双分子亲核攻击。

  DOI：

  10.1039/j29700000510
• 作为产物：
  描述：

  tris(3-nitrophenyl) (1,1,2,2-tetrachloropropyl)phosphorimidate 在 水 作用下， 生成 tris(m-nitrophenyl) phosphate
  参考文献：
  名称：

  Shevchenko,V.I. et al., Journal of general chemistry of the USSR, 1970, vol. 40, # 5, p. 991 - 995

  摘要：

  DOI：

文献信息

• Activating Water: Important Effects of Non-leaving Groups on the Hydrolysis of Phosphate Triesters
  作者：Anthony J. Kirby、Michelle Medeiros、Pedro S. M. Oliveira、Elisa S. Orth、Tiago A. S. Brandão、Eduardo H. Wanderlind、Almahdi Amer、Nicholas H. Williams、Faruk Nome

  DOI：10.1002/chem.201101926

  日期：2011.12.23

  spontaneous hydrolysis of tris‐2‐pyridyl phosphate (TPP) is explained by the activating effects of the non‐leaving (“spectator”) groups on POAr cleavage, and not by intramolecular catalysis. Previous work on phosphate‐transfer reactions has concentrated on the contributions to reactivity of the nucleophile and the leaving group, but our results make clear that the effects of the non‐leaving groups on phosphorus

  三-2-吡啶基磷酸酯的自发水解的高速率（TPP）是通过在P上的非离开（“旁观者”）基团的激活作用说明OAr裂解，而不是通过分子内催化。先前有关磷酸盐转移反应的研究主要集中在亲核试剂和离去基团对反应活性的贡献上，但我们的结果表明，非离去基团对磷的影响同样重要。对三个系列的磷酸三酯的速率测量结果表明，对于自发水解反应，对非离去基团的敏感性非常重要，尽管对于具有良好亲核试剂的反应，其敏感性要小得多。有在离开和非离去基团与示出了用于两个较低值的更具反应性的三芳基系统之间的三芳基和二烷基芳基三酯在灵敏度明显的差异β LG和β NLG。相邻的吡啶氮原子对TPP水解的分子内催化作用微不足道，主要是因为它们的碱度低。
• Nucleophilic Attack of Salicylhydroxamate Ion at C═O and P═O Centers in Cationic Micellar Media
  作者：Manmohan Lal Satnami、Sunita Dhritlahre、Rekha Nagwanshi、Indrapal Karbhal、Kallol K. Ghosh、Faruk Nome

  DOI：10.1021/jp1066549

  日期：2010.12.23

  incorporation of hydroxamate ion. Plots of the pseudo-first-order rate constant, kobs, log kobs, fraction of hydroxamic acid ionized, αSHA− and αSA2−, vs pH showed bifunctional nucleophilicity of hydroxamic acid under micellar condition. Plotting kobs vs [SHA]T gave a straight line with intercept k0. This indicates that hydroxamate ions are very strong nucleophiles for nucleophilic attack at the C and

  所述SAlicylhydroxamate阴离子（SHA之间的反应- ）和p硝基苯基苯甲酸酯（PNPB），三（3-硝基苯基）酯（TRIS），和双（2,4-二硝基苯基）酯（BDNPP）已经被动力学检查。α-亲核试剂，SHA - ，并入十六烷基三甲基溴（CTAB）胶束加速三（3-硝基苯基）酯（TRIS）在pH范围6.7-11.4的去磷酸化。在CTAB中SHA的1.0 mM时，SHA的亲核性遵循反应性的顺序，PNPB（C═O，羧酸酯）> TRIS（P═O，三酯）> BDNPP（P═O，二酯），和单阴离子SHA -和双阴离子SA 2-是反应性物质。临界胶束浓度，CMC，十六烷基三甲基铵（CTAB）降低和分数电离常数，α，随着SHA的浓度增加- 。在反应条件（pH 9.2，硼酸盐缓冲液）下添加1和10 mM SHA导致胶束表面饱和，并为胶束掺入异羟肟酸离子提供了定性信息。伪一级速率常数的曲线，ķ OBS，日志ķ
• <i>O</i>-Nucleophilicity of Hydroxamate Ions for Cleavage of Carboxylate and Phosphate Esters in Cationic Micelles
  作者：MANMOHAN L. SATNAMI、INDRAPAL KARBHAL、HITESH K. DEWANGAN

  DOI：10.1002/kin.20852

  日期：2014.8

  kinetically. Over the pH range of 6.7–11.4, the α‐nucleophile (HA−) accelerates deacylation of PNPB and dephosphorylation of TRIS (in cetyltrimethylammonium bromide (CTAB) micelle, 2.0 × 10−3 M). The salicylhydroxamate ion encountered effective catalysis than AHA−, BHA−, and MBHA− ions. The monoanionic SHA− and dianionic SA2− forms of salicylhydroxamic acid are the reactive species. The hydroxamic acid concentration–dependent

  异羟肟酸的亲核反应性（HA - ）结构RCONHO的离子- [R = CH 3（acetohydroxamate，AHA - ），C 6 H ^ 5（benzohydroxamate，BHA - ），2--OHC 6 H ^ 4（SAlicylhydroxamate，SHA - ）和4-CH 3 OC 6 H ^ 4（4- methoxbenzohydroxamate，MBHA -）]为水解p硝基苯基苯甲酸酯（PNPB），三（3-硝基苯基）酯（TRIS）和磷酸二（2,4-二硝基苯基）（BDNPP）进行了动力学检查。在pH范围6.7-11.4，α-亲核试剂（HA - ）加速时的脱酰PNPB和去磷酸化TRIS（在十六烷基三甲基溴（CTAB）胶束，2.0×10 -3 M）。所述SAlicylhydroxamate离子遇到有效催化比AHA - ，BHA - ，和MBHA -离子。单阴离子SHA -和二阴离子SA
• Bis(m-nitrophenyl) and bis(p-nitrophenyl) esters and the phosphorodiamidate of thymidine 5'-phosphate as potential sources of intracellular thymidine 5'-phosphate in mouse cells in culture
  作者：Ram R. Chawla、Jerome J. Freed、Alexander Hampton

  DOI：10.1021/jm00378a036

  日期：1984.12

  Thymidine 5'-phosphate (TMP) derivatives with masked phosphate groups were synthesized in tritiated form from [methyl-3H]thymidine. They were of interest as models for 5' nucleotide derivatives that might be able to permeate mammalian cells and then liberate intracellular antimetabolite 5' nucleotides by loss of the masking groups. Mouse L fibroblasts were grown in vitro in the presence of 1 mM 5'-amino-5'-deoxythymidine, which was found to suppress greater than 99% of cellular thymidine kinase activity while inhibiting the rate of cell division by only 30%. The TMP derivatives were less effective than thymidine in labeling the deoxyribonucleic acid (DNA) of the L cells. The labeling was inhibited 95-99% by 5'-amino-5'-deoxythymidine, indicating that it represented incorporation into DNA of [3H]thymidine formed from degradation of the test compounds. No evidence was obtained that the compounds acted as sources of intracellular TMP by cell permeation followed by loss of phosphate blocking groups. Similar studies yielded no evidence that the bis(m-nitrophenyl) ester of TMP produced intracellular TMP by that route in the LM(TK-) strain of L cells that are genetically deficient in thymidine kinase.
• PEPTIDYL COMPOUNDS COMPRISING AN ITIM MOTIF WHICH REGULATE HEMATOPOIETIC FUNCTION AND THEIR USE
  申请人：NATIONAL JEWISH CENTER FOR IMMUNOLOGY AND RESPIRATORY MEDICINE

  公开号：EP0812330A2

  公开（公告）日：1997-12-17