O-ethyl S-phenyl phenylphosphonothioate

• 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: O-ethyl S-phenyl phenylphosphonothioate
• 英文别名: [Ethoxy(phenylsulfanyl)phosphoryl]benzene；[ethoxy(phenylsulfanyl)phosphoryl]benzene
• 化学式: C₁₄H₁₅O₂PS
• 分子量: 278.312
• InChiKey: UELKUXRHWGALPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl Phenylphosphinate 在 sulfur 作用下， 以 1,4-二氧六环 、 乙醚 、 乙酸乙酯 为溶剂， 反应 18.0h， 生成 O-ethyl S-phenyl phenylphosphonothioate
  参考文献：
  名称：

  硫代磷酸二酯及相关化合物与二芳基碘盐的无金属 S-芳基化

  摘要：

  我们使用二芳基碘盐开发了硫代磷酸二酯的直接无金属S-芳基化。该方法允许在简单条件下制备范围广泛的S-芳基硫代磷酸酯，包括复杂分子（例如，二核苷酸或 TADDOL 衍生物），以及在硫属元素芳基化的其他相关有机磷化合物。反应在磷原子处完全保留立体异构中心的情况下进行，从而方便地获得 P-手性产物。使用DFT计算建立了反应机理。

  DOI：

  10.1021/acs.orglett.2c04310

文献信息

• Synthesis of P(O)-S organophosphorus compounds by dehydrogenative coupling reaction of P(O)H compounds with aryl thiols in the presence of base and air
  作者：Wei He、Xiao Hou、Xinjin Li、Liang Song、Qing Yu、Zhongwei Wang

  DOI：10.1016/j.tet.2017.04.035

  日期：2017.6

  The synthesis method of P(O)-S organophosphorus compounds by dehydrogenative coupling reaction of P(O)H compounds and aryl thiols was developed. The reaction was carried in the presence of a base and air, and exhibited good characters such as metal-free, mild reaction temperature, excellent substrate tolerance and with moderate to good yields. A plausible mechanism was proposed.

  提出了P（O）H化合物与芳基硫醇脱氢偶联反应合成P（O）-S有机磷化合物的方法。该反应在碱和空气存在下进行，并表现出良好的特性，例如无金属，温和的反应温度，优异的底物耐受性以及中等至良好的产率。提出了一个合理的机制。
• TBPB-promoted metal-free synthesis of thiophosphinate/phosphonothioate by direct P–S bond coupling
  作者：Jichao Wang、Xin Huang、Zhangqin Ni、Sichang Wang、Jun Wu、Yuanjiang Pan

  DOI：10.1039/c4gc00944d

  日期：——

  An efficient, metal-free method for synthesizing thiophosphinate or phosphonothioate by direct P–S bond coupling at room temperature is reported.

  一种在室温下通过直接P-S键偶联合成噻磷酸酯或磷硫酸酯的高效无金属方法被报道。
• Direct synthesis of thiophosphates by reaction of diphenylphosphine oxide with sulfonyl chlorides
  作者：Wei He、Zhiming Wang、Xinjin Li、Qing Yu、Zhongwei Wang

  DOI：10.1016/j.tet.2016.10.012

  日期：2016.11

  A new method for the synthesis of thiophosphates by reductive coupling reaction of diphenylphosphine oxide and sulfonyl chlorides has been developed. The reaction is metal-free and needs no additives, affording various aryl and alkyl substituted thiophosphates in good to excellent yields under mild conditions.

  开发了一种通过二苯基膦氧化物与磺酰氯的还原偶联反应合成硫代磷酸盐的新方法。该反应不含金属，不需要添加剂，可以在温和条件下以良好或优异的收率得到各种芳基和烷基取代的硫代磷酸酯。
• Synthesis of <i>S</i>-Aryl Phosphorothioates by Copper-Catalyzed Phosphorothiolation of Diaryliodonium and Arenediazonium Salts
  作者：Liangliang Zhang、Pengbo Zhang、Xueqin Li、Jian Xu、Guo Tang、Yufen Zhao

  DOI：10.1021/acs.joc.6b00925

  日期：2016.7.1

  Green methods for the synthesis of S-arylphosphorothioates have been developed based on copper catalyzed multicomponent reactions involving diaryliodonium/arenediazonium salts, elemental sulfur, and P(O)H compounds. Most target products are obtained with these two methods in good to high yields at room temperature. These transformations allow the direct formation P-S and C-S bonds in one reaction.

  基于铜催化的多组分反应，包括二芳基碘鎓/芳烯二唑鎓盐，元素硫和P（O）H化合物，已经开发了绿色的合成S-芳基硫代磷酸酯的方法。通过这两种方法，大多数目标产物在室温下均能以良好或高收率获得。这些转变允许在一个反应​​中直接形成PS和CS键。
• Metal-free direct arylation of dialkyl phosphonates for the synthesis of mixed alkyl aryl phosphonates
  申请人：The Board of Regents of the Nevada System of Higher Education on Behalf of the University of Nevada, Las Vegas

  公开号：US10927135B2

  公开（公告）日：2021-02-23

  Provided herein are phosphates, thiophosphates, phosphonates, and phosphinates, methods of making same, and methods of using these compounds and methods for the generation of pharmaceutically relevant phosphate, phosphonate, and phosphinate analogs. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本发明提供了磷酸盐、硫代磷酸盐、膦酸盐和膦酸盐、其制造方法、使用这些化合物的方法以及生成药用磷酸盐、膦酸盐和膦酸盐类似物的方法。本摘要旨在作为在特定技术领域进行搜索的扫描工具，并非对本发明的限制。