diethyl (4-methylbenzoyl)phosphonate | 2942-54-3

• 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 (4-methylbenzoyl)phosphonate
• 英文别名: Phosphonic acid, (4-methylbenzoyl)-, diethyl ester；diethoxyphosphoryl-(4-methylphenyl)methanone
• CAS: 2942-54-3
• 化学式: C₁₂H₁₇O₄P
• 分子量: 256.238
• InChiKey: GESNSNGXHITUQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  123-124 °C(Press: 0.05 Torr)
• 密度：
  1.1472 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (4-methylbenzoyl)phosphonate 在 甲醇 、 偶氮二异丁腈 、 碘代三甲硅烷 、 potassium tert-butylate 、 N,O-双(三甲基硅烷基)三氟乙酰胺 作用下， 以 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 27.0h， 生成 [Difluoro-[4-[(2-pyridin-2-ylimidazol-1-yl)methyl]phenyl]methyl]phosphonic acid
  参考文献：
  名称：

  Rational Design of Selective Organoruthenium Inhibitors of Protein Tyrosine Phosphatase 1B

  摘要：

  Protein tyrosine phosphatases (PTPs) belong to a large family of important regulatory enzymes involved in vital mammalian signaling pathways. Selective inhibitors of PTPs are highly valuable from a therapeutic standpoint given their association with various pathological conditions. One such target is PTP-1B which has previously been linked to diabetes and cancer. However, developing a selective inhibitor against PTP-1B has proven to be daunting because the enzyme shares a high degree of structural homology with TC-PTP, an essential PTP involved in modulating immune functions. To address this challenge, a series of organoruthenium complexes was developed to bind at the PTP substrate-binding site while simultaneously target the peripheral structural space. By capitalizing on the potential difference in the structural environment proximal to the active site between different PTPs, selectivity toward PTP-1B over TC-PTP was improved, paving the way for organoruthenium complexes as selective PTP-1B metalloinhibitors.

  DOI：

  10.1021/ic301884j
• 作为产物：
  描述：

  diethyl α-trimethylsilyloxy-4-methylbenzylphosphonate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 以74%的产率得到diethyl (4-methylbenzoyl)phosphonate
  参考文献：
  名称：

  A convenient and mild protocol for preparation of α –trimethylsilyloxyphosphonates using sulfamic acid and their oxidation to α – ketophosphonates in the presence of N-bromosuccinimide

  摘要：

  DOI：

  10.24820/ark.5550190.p011.603

文献信息

• Pd-catalyzed carbonylative access to aroyl phosphonates from (hetero)aryl bromides
  作者：Zhong Lian、Hongfei Yin、Stig D. Friis、Troels Skrydstrup

  DOI：10.1039/c5cc02085a

  日期：——

  This first carbonylative coupling employing a phosphorus-based nucleophile provides easy and safe access to acyl phosphonates under mild conditions.

  这种首次使用磷基亲核试剂的羰基化偶联反应在温和条件下提供了对酰基膦酸酯的简便安全访问。
• Visible photocatalysis of novel oxime phosphonates: synthesis of β-aminophosphonates
  作者：Yong-Hong Li、Chun-Hai Wang、Su-Qian Gao、Feng-Ming Qi、Shang-Dong Yang

  DOI：10.1039/c9cc06075h

  日期：——

  A novel type of oxime phosphonate was synthesized and used in the intermolecular cascade radical addition reaction of alkenes to access β-aminophosphonates via visible-light-driven N-centered iminyl radical-mediated and redox-neutral selective C–P single-bond cleavage in an active phosphorus radical route. The procedure is characterized by its ability to achieve the construction of Csp3–P and Csp3–N

  合成了一种新型肟肟酸酯，并将其用于烯烃的分子间级联自由基加成反应中，通过可见光驱动的N中心亚胺基自由基介导的氧化还原中性选择性C–P单键裂解来获得β-氨基膦酸酯。活性磷自由基途径。该方法的特点是无需氧化剂和碱即可实现Csp 3 -P和Csp 3 -N键的构建。
• Benzoylphosphonate-Based Photoactive Phosphopeptide Mimetics for Modulation of Protein Tyrosine Phosphatases and Highly Specific Labeling of SH2 Domains
  作者：André Horatscheck、Stefan Wagner、Jutta Ortwein、Boo Geun Kim、Michael Lisurek、Samuel Beligny、Anja Schütz、Jörg Rademann

  DOI：10.1002/anie.201201475

  日期：2012.9.10

  A light switch for phosphotyrosine‐ recognizing proteins: Irradiation of the bioisosteric benzoylphosphonate suffices to “turn off” the activity of target proteins and to label them covalently (see scheme). Photoactive bioisosters may find applications in functional cell biology, bioanalytics, and proteome research.

  磷酸酪氨酸识别蛋白的一个电灯开关：辐照生物立体异构的苯甲酰基膦酸酯足以“关闭”目标蛋白的活性并对其进行共价标记（参见方案）。光敏生物等排体可能会在功能细胞生物学，生物分析和蛋白质组学研究中找到应用。
• Nicotinium Dichromate (=3-Carboxypyridinium Dichromate; NDC) as an Efficient Reagent for the Oxidative Deamination of Amines and Aminophosphonates
  作者：Sara Sobhani、Sima Aryanejad、Mahdi Faal Maleki

  DOI：10.1002/hlca.201100404

  日期：2012.4

  A new method for the efficient synthesis of aldehydes, ketones, and oxophosphonates from various types of amines (primary and secondary) and aminophosphonates via oxidative deamination by nicotinium dichromate (=3‐carboxypyridinium dichromate; NDC) is described.

  用于从多种类型的胺（伯和仲）和氨基膦酸盐醛，酮，和oxophosphonates的有效合成的新方法通过被描述;氧化脱氨通过nicotinium重铬酸（NDC = 3-羧基吡啶基重铬酸盐）。
• Oxidative Deamination of α-Aminophosphonates and Amines by Zinc Dichromate Trihydrate (ZnCr2O7˙3H2O) under Solvent-Free Conditions at Room Temperature
  作者：Sara Sobhani、Mahdi Maleki

  DOI：10.1055/s-0029-1219174

  日期：2010.2

  A novel method for the rapid and efficient conversion of a variety ot α-aminophosphonates to α-ketophosphonates using ZnCr 2 O 7 ·3H 2 O via oxidative deamination under solvent-free conditions at room temperature is described. This method is also applicable to the rapid and highly selective oxidation of various types of ordinary amines (primary and secondary) to aldehydes and ketones in good to high

  描述了一种使用 ZnCr 2 O 7 ·3H 2 O 在室温下无溶剂条件下通过氧化脱氨基快速有效地将多种 α-氨基膦酸酯转化为 α-酮膦酸酯的新方法。该方法也适用于各种类型的普通胺（伯胺和仲胺）以良好到高产率快速和高选择性氧化成醛和酮。