O,O-dibenzyl S-phenylphosphorothioate | 1608108-22-0

• 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,O-dibenzyl S-phenylphosphorothioate
• 英文别名: [Phenylmethoxy(phenylsulfanyl)phosphoryl]oxymethylbenzene；[phenylmethoxy(phenylsulfanyl)phosphoryl]oxymethylbenzene
• CAS: 1608108-22-0
• 化学式: C₂₀H₁₉O₃PS
• 分子量: 370.409
• InChiKey: CNTXVOSGFBQEAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  亚磷酸二苄酯 、 二苯基碘三氟甲烷磺酸盐 在 copper acetylacetonate 、 sulfur 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以85%的产率得到O,O-dibenzyl S-phenylphosphorothioate
  参考文献：
  名称：

  铜催化二芳基碘鎓盐和Arenediazonium盐的硫代磷酸酯化反应合成S-芳基硫代磷酸酯。

  摘要：

  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。

  DOI：

  10.1021/acs.joc.6b00925

文献信息

• Magnetically recyclable Cu-BTC@Fe₃O₄ composite-catalyzed C_(aryl)–S–P bond formation using aniline, P(O)H compounds and sulfur powder
  作者：Liang Wang、Sen Yang、Le Chen、Sheng Yuan、Qun Chen、Ming-Yang He、Zhi-Hui Zhang

  DOI：10.1039/c7cy00467b

  日期：——

  Cu-BTC@Fe3O4 composite was prepared and exhibited good catalytic activity toward the synthesis of S-aryl phosphorothioates. This three-component reaction involved the coupling of in situ generated aryl diazonium salts from aniline, R2P(O)H, and sulfur powder, allowing the facile and direct formation of C(aryl)-S-P bonds. A broad scope of substrates survived the reaction conditions to afford the corresponding

  制备了Cu-BTC @ Fe3O4复合材料，对合成S-芳基硫代磷酸酯具有良好的催化活性。此三组分反应涉及从苯胺，R2P（O）H和硫粉中原位生成的芳基重氮盐偶联，从而可以轻松，直接地形成C（芳基）-SP键。各种各样的底物在反应条件下均能幸存，从而以良好或优异的产率提供相应的产物。而且，该多相催化剂可以在六个循环后被磁回收和再利用而其活性没有显着损失。
• Rongalite-promoted transition metal-free synthesis of S-aryl phosphorothioates
  作者：Min-xiao Xu、Kai-ming Zhang

  DOI：10.1016/j.mencom.2022.05.033

  日期：2022.5

  The improved procedure for the synthesis of S-aryl phosphorothioates from dialkyl phosphites (H-phosphonates), aryl iodides and elemental sulfur deals with the application of rongalite (sodium hydroxy-methanesulfinate) as the radical promoter. The reactions proceeded smoothly to give S-aryl phosphorothioates in good yields.

  从亚磷酸二烷基酯（H-膦酸酯）、芳基碘化物和元素硫合成 S-芳基硫代磷酸酯的改进程序涉及使用雕白粉（羟基甲烷亚磺酸钠）作为自由基促进剂。反应顺利进行，以良好的收率得到硫代磷酸 S-芳基酯。
• Environmentally benign synthesis and antimicrobial study of novel chalcogenophosphates
  作者：Shubhanjan Mitra、Sayani Mukherjee、Sukanta K. Sen、Alakananda Hajra

  DOI：10.1016/j.bmcl.2014.03.008

  日期：2014.5

  We report in this work an environmentally benign zinc mediated synthesis of aryl and benzyl phosphorochalcogenoates in ethanol within a short reaction time. In vitro antimicrobial study along with statistical analysis and seed germination assay were performed. These chalcogenophosphates possess strong antimicrobial activity against the reference strains. The antibacterial activity was determined against four standard strains (Bacilus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa). The antifungal activity was evaluated against one fungal strain Candida albicans. (C) 2014 Elsevier Ltd. All rights reserved.
• 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。