diethyl (3-nitrophenyl)phosphonate | 89277-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl (3-nitrophenyl)phosphonate
• 英文别名: diethyl 3-nitrophenylphosphonate；diethyl m-nitrophenylphosphonate；(3-nitro-phenyl)-phosphonic acid diethyl ester；(3-Nitro-phenyl)-phosphonsaeure-diaethylester；Diethyl(3-nitrophenyl)phosphonate；1-diethoxyphosphoryl-3-nitrobenzene
• CAS: 89277-95-2
• 化学式: C₁₀H₁₄NO₅P
• 分子量: 259.199
• InChiKey: XULZFYBFQWRFDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  133-137 °C(Press: 0.2 Torr)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (3-nitrophenyl)phosphonate 在 tin(ll) chloride 、 盐酸 作用下， 以 乙醇 、 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 以0.638 g的产率得到(3-aminophenyl)phosphonate de diethyle
  参考文献：
  名称：

  Synthesis and Evaluation of Phosphorus Containing, Specific CDK9/CycT1 Inhibitors

  摘要：

  Although there is a significant effort in the design of a selective CDK9/CycT1 inhibitor, no compound has been proven to be a specific inhibitor of this kinase so far. The aim of this research was to develop novel and selective phosphorus containing CDK9/CycT1 inhibitors. Molecules bearing phosphonamidate, phosphonate, and phosphinate moieties were synthesized. Prepared compounds were evaluated in an enzymatic CDK9/CycT1 assay. The most potent molecules were tested in cell-based toxicity and HIV proliferation assays. Selectivity of shortlisted compounds against CDKs and other kinases was tested. The best compound was shown to be a highly specific, ATP-competitive inhibitor of CDK9/CycT1 with antiviral activity.

  DOI：

  10.1021/jm401742r
• 作为产物：
  描述：

  3-硝基苯磺酸 在 五氯化磷 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 diethyl (3-nitrophenyl)phosphonate
  参考文献：
  名称：

  Phosphorus analogs of .gamma.-aminobutyric acid, a new class of anticonvulsants

  摘要：

  A series of phosphorus compounds, designed as analogues of gamma-aminobutyric acid (GABA) in that they possess a P = O moiety separated by three atoms from an amino or acetamido group, was synthesized and tested by using in vitro GABAA and GABAB receptor binding, GABA uptake assays, and was examined for anticonvulsant activity. Weak GABAB receptor affinity was noted for one agent, whereas six compounds displayed moderate to high potencies as inhibitors of electroshock- and pentylenetetrazol-induced seizures. The best anticonvulsant effect was found with the (m-aminophenyl) phosphinic acid compounds, with members of this class selected for further study.

  DOI：

  10.1021/jm00371a017

文献信息

• Novel approach to metal-induced oxidative phosphorylation of aromatic compounds
  作者：M.N. Khrizanforov、S.O. Strekalova、K.V. Kholin、V.V. Khrizanforova、M.K. Kadirov、T.V. Gryaznova、Y.H. Budnikova

  DOI：10.1016/j.cattod.2016.06.001

  日期：2017.1

  electron donating substituents on the ring and some coumarins (coumarin, 6-methylcoumarin, 7-methylcoumarin) under the action of dialkyl H-phosphonate (RO)2P(O)H (R = Et, n-Bu, i-Pr), based on catalytic oxidation of arene and H-phosphonate (1:1) mixture in electrochemically mild conditions (room temperature, normal pressure) using the bimetallic catalyst system MnIIbpy/NiIIbpy (1%). This method produces a

  摘要 我们提出了一种在 H-膦酸二烷基酯 (RO)2P(O )H (R = Et, n-Bu, i-Pr)，基于使用双金属催化剂体系 MnIIbpy/ 在电化学温和条件（室温、常压）下催化氧化芳烃和 H-膦酸盐 (1:1) 混合物尼比比 (1%)。该方法以高产率（高达 70%）和 100% 的 H-膦酸盐转化率生产磷酸二烷基芳基酯。
• Cobalt Catalyzed C-P Bond Formation by Cross-Coupling of Boronic Acids with P(O)H Compounds in Presence of Zinc
  作者：Ian Hicks、Jonathan McTague、Tatiana Hapatsha、Rania Teriak、Parminder Kaur

  DOI：10.3390/molecules25020290

  日期：——

  In our current work, we have reported the first cobalt-catalyzed cross-coupling of arylboronic acid with alkyl/aryl phosphites under mild conditions. The reaction was carried out in the presence of zinc powder as an additive and ter-pyridine as a ligand. The use of non-precious cobalt salt makes the protocol advantageous, as it is inexpensive and more abundant than the previously used methods where

  在我们目前的工作中，我们报道了在温和条件下首次钴催化芳基硼酸与烷基/芳基亚磷酸酯的交叉偶联。该反应在锌粉作为添加剂和三联吡啶作为配位体的存在下进行。非贵金属钴盐的使用使该协议具有优势，因为它比以前使用的贵金属盐（Pd 和 Pt）的方法便宜且丰富。该反应底物范围广，产物收率良好。
• Cu₂O/TiO₂ nanoparticles as visible light photocatalysts concerning C(sp²)–P bond formation
  作者：Mona Hosseini-Sarvari、Fattaneh Jafari、Afshan Mohajeri、Nasim Hassani

  DOI：10.1039/c8cy00822a

  日期：——

  construction of an aromatic-phosphorus (Ar-P) bond under visible light irradiation using Cu2O/TiO2 nanoparticles as inexpensive and available photocatalysts. This protocol is a simple system without the use of any base, ligand, oxidant, or special conditions. This is the first report for the synthesis of arylphosphonates from arylhydrazines in visible light irradiation.

  已经开发出一种新颖有效的方法，用于在可见光照射下使用Cu 2 O / TiO 2纳米粒子作为廉价和可用的光催化剂来构建芳族磷（Ar-P）键。该方案是一个简单的系统，无需使用任何碱，配体，氧化剂或特殊条件。这是在可见光照射下由芳基肼合成芳基膦酸酯的第一份报告。
• Copper-Catalyzed C−P Bond Construction via Direct Coupling of Phenylboronic Acids with H-Phosphonate Diesters
  作者：Rongqiang Zhuang、Jian Xu、Zhenshi Cai、Guo Tang、Meijuan Fang、Yufen Zhao

  DOI：10.1021/ol200465z

  日期：2011.4.15

  A mild and efficient method was developed for the copper-catalyzed additions of H-phosphonate diesters to boronic acids under the copper catalyst system Cu2O/1,10-phenanthroline. To the best of our knowledge this finding is the first example of a copper-catalyzed synthesis of aryl phosphonates from arylboronic acids and H-phosphonate dialkyl esters.

  开发了一种温和有效的方法，用于在铜催化剂体系Cu 2 O / 1,10-菲咯啉下，将H-膦酸酯二酯铜催化添加到硼酸中。据我们所知，该发现是铜催化从芳基硼酸和H-膦酸酯二烷基酯合成芳基膦酸酯的第一个例子。
• An Improved Procedure for the Synthesis of Aryl Phosphonates by Palladium-Catalysed Cross-Coupling of Aryl Halides and Diethyl Phosphite in Polyethylene Glycol
  作者：Ping Wang、Jie Lu、Zhan-Hui Zhang

  DOI：10.3184/174751913x13686082295417

  日期：2013.6

  A general and greener protocol for the synthesis of aryl phosphonates by the cross-coupling of aryl halides and diethyl phosphite using tetrakis(triphenylphosphine)palladiume/triethylamine/polyethylene glycol 600 [Pd(PPh3)4/Et3N/PEG 600] as an efficient catalytic system has been developed. This procedure also avoids hazardous solvents and is therefore an eco-friendly alternative to the existing methods

  使用四（三苯基膦）钯/三乙胺/聚乙二醇 600 [Pd(PPh3)4/Et3N/PEG 600] 作为有效催化剂，通过芳基卤化物和亚磷酸二乙酯的交叉偶联合成芳基膦酸酯的通用且更环保的方案系统已经开发。该程序还避免了有害溶剂，因此是现有方法的环保替代品。