diphenyl(2-(phenylsulfonyl)ethyl)phosphine oxide | 65492-20-8

• 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(2-(phenylsulfonyl)ethyl)phosphine oxide
• 英文别名: [2-(Benzenesulfonyl)ethyl-phenylphosphoryl]benzene；[2-(benzenesulfonyl)ethyl-phenylphosphoryl]benzene
• CAS: 65492-20-8
• 化学式: C₂₀H₁₉O₃PS
• 分子量: 370.409
• InChiKey: RHIMWXCDKJTJCN-UHFFFAOYSA-N

物化性质

• 沸点：
  548.2±42.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯基乙烯基砜 、 Diphenylphosphine oxide 在 potassium carbonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 以30%的产率得到diphenyl(2-(phenylsulfonyl)ethyl)phosphine oxide
  参考文献：
  名称：

  碳酸钾促进烯烃与亚磷酸酯的亲核加成

  摘要：

  开发了一种由碳酸钾促进的亚磷酸酯对烯烃的轻松氢膦酰化。反应特点包括易于处理、环境友好和避免使用强碱。该反应可以耐受多种烯烃，产率中等至极好。

  DOI：

  10.1055/s-0040-1707852

文献信息

• Potassium Carbonate Promoted Nucleophilic Addition of Alkenes with Phosphites
  作者：Shengmei Guo、Zhenjun Huang、Wei Liu、Sen Li、Yutian Yang、Hu Cai

  DOI：10.1055/s-0040-1707852

  日期：2020.8

  A facile hydrophosphonylation of alkenes by phosphites promoted by potassium carbonate was developed. The reaction features include easy handling, environmental friendliness, and avoidance of the use of strong bases. A variety of alkenes are tolerated in this reaction, with moderate to excellent yields.

  开发了一种由碳酸钾促进的亚磷酸酯对烯烃的轻松氢膦酰化。反应特点包括易于处理、环境友好和避免使用强碱。该反应可以耐受多种烯烃，产率中等至极好。
• Visible Light‐Driven, Persulfate‐Mediated Hydrocarboxylation of Vinylsulfones
  作者：Ádám Márk Pálvölgyi、Fabian Scharinger、Thomas Bauhoff、Katharina Bica‐Schröder

  DOI：10.1002/adsc.202300654

  日期：2023.9.19

  accessible sodium formate as C1-source and K2S2O8 as reagent, a set of vinylsulfone substrates could be efficiently hydrocarboxylated in aqueous medium without any additional catalyst or reagent; and the concept could be also applied for direct hydroacylations, hydroalkylations and hydrophosphorylations. The control experiments clearly indicated that the reaction proceeds via radical mechanism without

  我们报告了一种可见光介导的乙烯砜衍生物自由基加氢羧化方法。使用廉价易得的甲酸钠作为C1源，K 2 S 2 O 8作为试剂，一组乙烯基砜底物可以在水介质中有效地加氢羧化，无需任何额外的催化剂或试剂；该概念也可应用于直接加氢酰化、加氢烷基化和加氢磷酸化。对照实验清楚地表明该反应通过自由基机制进行，没有生成电子供体-受体（EDA）复合物；支持K 2 S 2 O 8原位引发的工作模型形成CO 2自由基阴离子。
• N-Heterocyclic Carbene Catalyzed Carba-, Sulfa-, and Phospha-Michael Additions with NHC·CO₂ Adducts as Precatalysts
  作者：Morgan Hans、Lionel Delaude、Jean Rodriguez、Yoann Coquerel

  DOI：10.1021/jo500108a

  日期：2014.3.21

  N-heterocyclic carbene catalyzed Michael additions have been revisited with 1,3-dialkyl- or 1,3-diarylimidazol(in)ium-2-carboxylates, that is, NHC center dot CO2 adducts, as the source of the free NHC catalysts in solution. Using these precatalysts, a number of efficient carba-, sulfa-, and phospha-Michael additions were achieved very conveniently, without the need for an external strong base to generate the NHC by deprotonation of an azolium salt. To further expand the scope of the procedure, some NHC-catalyzed sulfa-Michael/aldol organocascades were also investigated.
• Kauffmann,T.; Joussen,R., Chemische Berichte, 1977, vol. 110, p. 3930 - 3934
  作者：Kauffmann,T.、Joussen,R.

  DOI：——

  日期：——
• Charge Separation in Metal‐Organic Framework Enables Heterogeneous Thiol Catalysis
  作者：Shengxian Cheng、Jing Ouyang、Muqing Li、Yingxue Diao、Jiachen Yao、Fengxing Li、Yat‐For Lee、Herman Ho‐Yung SUNG、Ian Williams、Zhengtao Xu、Yangjian Quan

  DOI：10.1002/anie.202300993

  日期：2023.6.19

  Photoinduced metal–organic framework (MOF) enabled heterogeneous thiol catalysis has been achieved for the first time. MOF Zr‐TPDCS‐1, consisting of Zr₆‐clusters and TPDCS linkers (TPDCS=3,3′′,5,5′′‐tetramercapto[1,1′:4′,1′′‐terphenyl]‐4,4′′‐dicarboxylate), effectively catalyzed the borylation, silylation, phosphorylation, and thiolation of organic molecules. Upon irradiation, the fast electron transfer from TPDCS to Zr₆‐cluster is believed to facilitate the formation of the thiyl radical, a hydrogen atom transfer catalyst, which competently abstracts the hydrogen from borane, silane, phosphine, or thiol for generating the corresponding element radical to engender the chemical transformations. The elaborate control experiments evidenced the generation of thiyl radicals in MOF and illustrated a radical reaction pathway. The gram‐scale reaction worked well, and the product was conveniently separated via centrifugation and vacuum with a turnover number (TON) of ≈3880, highlighting the practical application potential of heterogeneous thiyl‐radical catalysis.

  摘要 首次实现了光诱导金属有机框架（MOF）异相硫醇催化。由 Zr6 簇和 TPDCS 连接器（TPDCS=3,3′′,5,5′′-四巯基[1,1′：4′,1′′-三联苯]-4,4′′-二甲酸酯），可有效催化有机分子的硼酸化、硅化、磷酸化和硫代化。在辐照下，TPDCS 与 Zr6 簇之间的快速电子转移被认为促进了硫基的形成，硫基是一种氢原子转移催化剂，能从硼烷、硅烷、膦或硫醇中抽取氢，生成相应的元素自由基，从而引发化学转化。精心设计的对照实验证明了硫基自由基在 MOF 中的生成，并说明了自由基反应途径。克级反应效果良好，产物经离心和真空分离后，周转次数（TON）≈3880，凸显了异相硫基自由基催化的实际应用潜力。