(4-硝基苄基)膦酸 | 1205-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4-硝基苄基)膦酸
• 英文名称: 4-nitrobenzylphosphonic acid
• 英文别名: p-nitrobenzylphosphonic acid；(4-Nitro-benzyl)-phosphonsaeure；(4-Nitro-benzyl)-phosphonic acid；(4-nitrophenyl)methylphosphonic acid
• CAS: 1205-62-5
• 化学式: C₇H₈NO₅P
• 分子量: 217.118
• InChiKey: FZNXRFYRXBFQMX-UHFFFAOYSA-N

物化性质

• 熔点：
  222-228°C
• 沸点：
  494.0±47.0 °C(Predicted)
• 密度：
  1.587±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  (4-硝基苄基)膦酸 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 4-硝基甲苯
  参考文献：
  名称：

  对硝基苄基膦酸光化学 C-P 键裂解产生单体偏磷酸根阴离子制备烷基磷酸二氢盐

  摘要：

  烷基磷酸二氢盐通过可能涉及单体偏磷酸根阴离子作为中间体的程序制备。该反应中使用的单体偏磷酸根阴离子是通过对硝基苄基膦酸二阴离子的光化学 C-P 键断裂产生的。对硝基苄基膦酸和 1,8-二氮杂双环 [5.4.0] 十一碳-7-烯（或 2,2,6,6-四甲基哌啶）的 1:2 摩尔混合物在过量醇中的光解得到磷酸二氢烷基酯良好的产量。

  DOI：

  10.1246/bcsj.59.1505
• 作为产物：
  描述：

  苯基膦酸二乙酯 在 盐酸 、 硫酸 、 水 、 硝酸 作用下， 反应 24.67h， 生成 (4-硝基苄基)膦酸
  参考文献：
  名称：

  Crystal structures of the apo form and a complex of human LMW-PTP with a phosphonic acid provide new evidence of a secondary site potentially related to the anchorage of natural substrates

  摘要：

  Low molecular weight protein tyrosine phosphatases (LMW-PTP, EC 3.1.3.48) are a family of single-domain enzymes with molecular weight up to 18 kDa, expressed in different tissues and considered attractive pharmacological targets for cancer chemotherapy. Despite this, few LMW-PTP inhibitors have been described to date, and the structural information on LMW-PTP druggable binding sites is scarce. In this study, a small series of phosphonic acids were designed based on a new crystallographic structure of LMW-PTP complexed with benzylsulfonic acid, determined at 2.1 angstrom. In silico docking was used as a tool to interpret the structural and enzyme kinetics data, as well as to design new analogs. From the synthesized series, two compounds were found to act as competitive inhibitors, with inhibition constants of 0.124 and 0.047 mM. We also report the 2.4 angstrom structure of another complex in which LMW-PTP is bound to benzylphosphonic acid, and a structure of apo LMW-PTP determined at 2.3 angstrom resolution. Although no appreciable conformation changes were observed, in the latter structures, amino acid residues from an expression tag were found bound to a hydrophobic region at the protein surface. This regions is neighbored by positively charged residues, adjacent to the active site pocket, suggesting that this region might be not a mere artefact of crystal contacts but an indication of a possible anchoring region for the natural substrate-which is a phosphorylated protein. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.017

文献信息

• 2-[1H-Benzimidazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamides and 2-[benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamides as kinase inhibitors
  申请人：Aurrecoechea Natalia

  公开号：US20100081653A1

  公开（公告）日：2010-04-01

  2-[1H-benzimidazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamides and 2-[benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamides and their salts are kinase inhibitors, useful in the treatment of cancer.

  2-[1H-苯并咪唑-2(3H)-基]-2-(嘧啶-2-基)乙酰胺和2-[苯并噻唑-2(3H)-基]-2-(嘧啶-2-基)乙酰胺及其盐是激酶抑制剂，在癌症治疗中有用。
• Photochemical C–P Bond Cleavage of Nitrobenzylphosphonate Ions
  作者：Yoshiki Okamoto、Narimasa Iwamoto、Susumu Toki、Setsuo Takamuku

  DOI：10.1246/bcsj.60.277

  日期：1987.1

  Whereas in an aqueous solution 1,2-bis(4-nitrophenyl)ethane was produced as a main product, in an alcohol solution only p-nitrotoluene was produced. This photolysis may proceed via intramolecular electron transfer from PO32− group to nitro aromatic moiety to form an excited state, which undergoes C–P bond cleavage to give p-nitrobenzyl anion and monomeric metaphosphate anion as intermediates. The C–P

  在紫外线照射下，对硝基苄基膦酸根离子的 C-P 键在醇水溶液中以约 0.7 的量子产率裂解，得到 1,2-双（4-硝基苯基）乙烷、对硝基甲苯、正磷酸盐和烷基磷酸二氢盐。在水溶液中，主要产物是 1,2-双（4-硝基苯基）乙烷，而在醇溶液中仅产生对硝基甲苯。这种光解可以通过从 PO32− 基团到硝基芳族部分的分子内电子转移进行，形成激发态，经过 C-P 键断裂，得到对硝基苄基阴离子和单体偏磷酸根阴离子作为中间体。对硝基苄基膦酸根离子的 C-P 键断裂比邻-和间-硝基苄基膦酸根离子更容易发生。
• Phosphonated Fluoroquinolones, Antibacterial Analogs Thereof, and Methods for the Prevention and Treatment of Bone and Joint Infections
  申请人：Delorme Daniel

  公开号：US20080287396A1

  公开（公告）日：2008-11-20

  The present invention relates to phosphonated fluoroquinolones, antibacterial analogs thereof, and methods of using such compounds. These compounds are useful as antibiotics for prevention and/or the treatment of bone and joint infections, especially for the prevention and/or treatment of osteomyelitis.

  本发明涉及磷酸化氟喹诺酮及其抗菌类似物，以及使用这些化合物的方法。这些化合物可用作抗生素，用于预防和/或治疗骨骼和关节感染，特别是用于预防和/或治疗骨髓炎。
• PHOTOCHEMICAL C–P BOND CLEAVAGE OF (p-NITOROPHENYL)METHYLPHOSPHONIC ACID
  作者：Yoshiki Okamoto、Narimasa Iwamoto、Setsuo Takamuku

  DOI：10.1246/cl.1984.2091

  日期：1984.12.5

  (p-Nitrophenyl)methylphosphonic acid underwent easily photochemical C–P bond cleavage in alkaline 80% ethanol solution, resulting in the formation of p-nitrotoluene, orthophosphate, and ethyl phophate. In acidic solution, the phosphonic acid was stable on irradiation.

  （对硝基苯基）甲基膦酸在 80% 的碱性乙醇溶液中容易发生光化学 C-P 键断裂，形成对硝基甲苯、正磷酸盐和磷酸乙酯。在酸性溶液中，膦酸在辐照下是稳定的。
• Photochemical carbon–phosphorus bond cleavage of nitro-substituted benzylphosphonic acids
  作者：Yoshiki Okamoto、Narimasa Iwamoto、Setsuo Takamuku

  DOI：10.1039/c39860001516

  日期：——

  Upon u.v.-irradiation, the C–P bond of p-nitrobenzylphosphonate is more readily cleaved to give a monomeric metaphosphate anion as intermediate than those of o- and m-derivatives.

  在紫外线照射，的C--P键p -nitrobenzylphosphonate更容易裂解，得到单体偏阴离子作为比的中间ö -和米-衍生物。