diphenyl (3-nitrophenyl)phosphonate | 89277-96-3

• 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: diphenyl (3-nitrophenyl)phosphonate
• 英文别名: 1-Diphenoxyphosphoryl-3-nitrobenzene；1-diphenoxyphosphoryl-3-nitrobenzene
• CAS: 89277-96-3
• 化学式: C₁₈H₁₄NO₅P
• 分子量: 355.287
• InChiKey: YIPWGKZPORRLKV-UHFFFAOYSA-N

物化性质

• 沸点：
  486.5±37.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  diphenyl (3-nitrophenyl)phosphonate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 3-Diphenoxyphosphorylaniline
  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
• 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 diphenyl (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

• Radical Arylation of Triphenyl Phosphite Catalyzed by Salicylic Acid: Mechanistic Investigations and Synthetic Applications
  作者：Manel Estruch-Blasco、Diego Felipe-Blanco、Irene Bosque、Jose C. Gonzalez-Gomez

  DOI：10.1021/acs.joc.0c00795

  日期：2020.11.20

  arylphosphonates at 20 °C within 1–2 h is reported using inexpensive SA as the catalytic promoter of the reaction. Mechanistic investigations suggest that the reaction proceeds via radical–radical coupling, consistent with the so-called persistent radical effect. The reaction tolerated a wide range of functional groups and heteroaromatic moieties. The synthetic usefulness and the unique reactivity of the

  据报道，使用廉价的SA作为反应的催化促进剂，可在20°C下1-2小时内合成一种简单且可扩展的方法，以合成二苯基芳基膦酸酯。机理研究表明，该反应通过自由基与自由基的耦合进行，这与所谓的持久自由基效应相一致。该反应耐受各种官能团和杂芳族部分。在不同的一步转化中证明了所得膦酸酯的合成有用性和独特的反应性。
• 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。
• Metal-Free Aromatic Carbon–Phosphorus Bond Formation via a Sandmeyer-Type Reaction
  作者：Shuai Wang、Di Qiu、Fanyang Mo、Yan Zhang、Jianbo Wang

  DOI：10.1021/acs.joc.6b01820

  日期：2016.12.2

  proceeds smoothly at room temperature without the exclusion of moisture or air. This phosphorylation reaction tolerates a wide range of functional groups and affords the phosphorylation products in moderate to good yields, thus providing a valuable method for the formation of aromatic carbon–phosphorus bonds.

  开发了一种有效的无金属磷酸化方法，该方法基于以芳胺为原料的桑德迈型转化。该转变在室温下平稳进行，没有水分或空气。这种磷酸化反应可耐受各种官能团，并以中等至良好的产率提供磷酸化产物，从而为形成芳族碳-磷键提供了一种有价值的方法。
• Visible Light‐Driven, Photocatalyst‐Free Arbuzov‐Like Reaction via Arylazo Sulfones
  作者：Di Qiu、Chang Lian、Jinshan Mao、Yi Ding、Zerong Liu、Liyan Wei、Maurizio Fagnoni、Stefano Protti

  DOI：10.1002/adsc.201900953

  日期：2019.11.19

  A visible light‐induced formation of Aryl‐Phosphorous bonds starting from arylazo sulfones and triaryl (or trialkyl)phosphites in the absence of any photoredox catalyst and any additives was developed. This reaction showed a broad substrate scope and afforded (hetero)aryl phosphonates in good yields and in up to the gram scale.

  在不存在任何光氧化还原催化剂和任何添加剂的情况下，从芳基偶氮砜和三芳基（或三烷基）亚磷酸酯开始可见光诱导的芳基-磷键形成。该反应显示出较宽的底物范围，并以良好的收率和至多克级提供了（杂）芳基膦酸酯。