S-(4-acetamidophenyl)diphenylphosphinothioate | 99234-84-1

• 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: S-(4-acetamidophenyl)diphenylphosphinothioate
• 英文别名: N-(4-diphenylphosphorylsulfanylphenyl)acetamide
• CAS: 99234-84-1
• 化学式: C₂₀H₁₈NO₂PS
• 分子量: 367.408
• InChiKey: FSWDBBJYMNFIKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  溴苯 在 过氧化苯甲酸叔丁酯 、 碘 、 magnesium 、 potassium iodide 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 8.0h， 生成 S-(4-acetamidophenyl)diphenylphosphinothioate
  参考文献：
  名称：

  TBPB-promoted metal-free synthesis of thiophosphinate/phosphonothioate by direct P–S bond coupling

  摘要：

  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。

  DOI：

  10.1039/c4gc00944d

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。
• Chloroform-based Atherton–Todd-type reactions of alcohols and thiols with secondary phosphine oxides generating phosphinothioates and phosphinates
  作者：Shan Li、Tieqiao Chen、Yuta Saga、Li-Biao Han

  DOI：10.1039/c5ra16015d

  日期：——

  Various valuable phosphinothioates and phosphinates including those with functional groups are readily prepared under mild reaction conditions via chloroform-based Atherton–Todd-type reactions of secondary phosphine oxides with alcohols and thiols, respectively.

  各种有价值的磷硫酸酯和磷酸酯，包括带有功能基团的那些，在温和的反应条件下通过氯仿基的Atherton-Todd型反应分别与醇和硫醇反应制备。
• Metal- and base-free reductive coupling reaction of P(O)–H with aryl/alkyl sulfonyl chlorides: a novel protocol for the construction of P–S–C bonds
  作者：Dungai Wang、Jinlong Zhao、Weigang Xu、Changwei Shao、Zheng Shi、Liang Li、Xinghua Zhang

  DOI：10.1039/c6ob02364a

  日期：——

  Novel and efficient synthesis of S-aryl/alkyl phosphinothioates from P(O)–H and aryl/alkyl sulfonyl chlorides under metal- and base-free conditions is described. This reaction provides an alternative strategy for the construction of P–S–C bonds in moderate to excellent yields. Moreover, this method can be readily applied to gram-scale preparation.

  描述了在无金属和无碱条件下由P（O）–H和芳基/烷基磺酰氯新型有效合成S-芳基/烷基硫代磷酸酯的方法。该反应为中等至极好的产率的P–S–C键的构建提供了另一种策略。而且，该方法可以容易地应用于克级制备。
• 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。
• Design of Photoactive Covalent Organic Frameworks as Heterogeneous Catalyst for Preparation of Thiophosphinates from Phosphine Oxides and Thiols
  作者：Huijie Qiao、Liting Yang、Xiubei Yang、Jialin Wang、Ya Chen、Lin Zhang、Wuxuan Sun、Lipeng Zhai、Liwei Mi

  DOI：10.1002/chem.202200600

  日期：2022.5.6

  Py-DMTA-COF exhibited better photocatalytic activity, broad substrate applicability, and excellent recycling capacity for the preparation of thiophosphinates from P(O)H compounds and thiols compared to Py-DMTPDA-COF. This methodology was further extended to the seamless gram-scale production of target phosphorothioate derivatives. The results demonstrate that COFs can provide a robust platform for

  由 4,4',4'',4'''-(pyrene-1,3,6,8-tetrayl)tetraaniline 和 2,5-dimethoxyterephthalaldehyde (Py-DMTA- COF) 或 2',5'-二甲氧基-[1,1':4',1''-三联苯]-4,4''-二甲醛 (Py-DMTPDA-COF) 在溶剂热条件下。这两种 COF 被进一步开发为用于合成硫代次膦酸盐的高效光催化平台。与 Py-DMTPDA-COF 相比，Py-DMTA-COF 在从 P(O)H 化合物和硫醇制备硫代次膦酸盐方面表现出更好的光催化活性、广泛的底物适用性和优异的回收能力。该方法进一步扩展到目标硫代磷酸酯衍生物的无缝克级生产。