S-propyl diphenylphosphinothioate | 52372-88-0

• 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: S-propyl diphenylphosphinothioate
• 英文别名: S-Propyl P,P-diphenylphosphinothioate；[phenyl(propylsulfanyl)phosphoryl]benzene
• CAS: 52372-88-0
• 化学式: C₁₅H₁₇OPS
• 分子量: 276.339
• InChiKey: CHZFYMWNIPIIMT-UHFFFAOYSA-N

物化性质

• 沸点：
  402.4±28.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

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 4.0h， 生成 S-propyl 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

• Dimethyl sulfoxide as a mild oxidant in S–P(O) bond construction: simple and metal-free approaches to phosphinothioates
  作者：Jian-Guo Sun、Wei-Zhi Weng、Ping Li、Bo Zhang

  DOI：10.1039/c6gc03115c

  日期：——

  In the presence of dimethyl sulfoxide (DMSO) as the mild oxidant and reaction medium, a simple and efficient protocol has been developed for the preparation of phosphinothioates via oxidative dehydrogenative...

  在以二甲亚砜（DMSO）作为弱氧化剂和反应介质的情况下，已开发出一种简单有效的方案，用于通过氧化脱氢反应制备硫代膦酸酯。
• Intramolecular nucleophilic displacement of halogen by phosphinate and thiophosphinate anions: relative rates of formation of five- and six-membered rings 1
  作者：Amirah Chaudhry、Martin J. P. Harger、Philippa Shuff、Alison Thompson

  DOI：10.1039/a900623k

  日期：——

  Intramolecular nucleophilic substitution transforms the phosphinate anions XCH2CH2(CH2)nCH2(Ph)P(O)O– (n = 0, 1; X = Br, Cl) (Et3NH+ salts; CH2Cl2 solution) into cyclic phosphinate esters 14 (n = 0, 1); unusually the five-membered ring product (n = 0) is formed only 4.3 (X = Br) or 5.7 (X = Cl) times faster than the six (n = 1). The analogous cyclisation of the thiophosphinate anions ClCH2CH2(CH2)nCH2(Ph)P(S)O–

  分子内亲核取代使次膦酸酯阴离子XCH 2 CH 2（CH 2）n CH 2（Ph）P（O）O –（n  = 0，1; X = Br，Cl）（Et 3 NH +盐； CH 2 Cl 2溶液）成环次膦酸酯14（n  = 0，1）; 异常的五元环的产物（Ñ  = 0）仅形成4.3（X =溴）或快于5.7（X = Cl）的倍六（Ñ  = 1）。硫代次膦酸酯阴离子ClCH 2 CH 2（CH 2）的类似环化n CH 2（Ph）P（S）O –（n = 0，1）得到的产物16（n = 0，1）的环上有硫原子；现在，五元环的形成速度比六元环快30倍，但仍具有适度的速率优势。
• Pseudohalogenation of Phosphites
  作者：Enxue Shi、Chengxin Pei

  DOI：10.1055/s-2004-834898

  日期：——

  A new type of Atherton-Todd reaction for a convenient pseudohalogenation of phosphites has been developed. Direct azidation, cyanation, and thiocyanation of (RO)2P(O)H (R = Et, i-Bu, Ph) were accomplished readily with sodium pseudohalides in acetonitrile under mild modified Atherton-Todd conditions. The corresponding phosphorochloridates were demonstrated by GC/MS to be the intermediates. Pseudohalogenations of ethyl phenylphosphinate and diphenylphosphine oxide were also investigated.

  开发了一种用于膦酸酯便捷伪卤化的Atherton-Todd反应新类型。在温和改良的Atherton-Todd条件下，通过乙腈中的钠伪卤化物，(RO)2P(O)H（R = Et, i-Bu, Ph）的直接叠氮化、氰化和硫氰化反应得以轻松完成。气相色谱/质谱（GC/MS）显示相应的磷酰氯化物是中间体。还研究了乙基苯膦酸酯和二苯基膦氧化物的伪卤化反应。
• Copper-catalyzed cross-dehydrogenative coupling of P(O)−H compounds with O-/S-nucleophiles
  作者：Lulu Si、Biquan Xiong、Shipan Xu、Longzhi Zhu、Yu Liu、Weifeng Xu、Ke-Wen Tang

  DOI：10.1016/j.jorganchem.2023.122670

  日期：2023.6

  The copper-catalyzed cross-dehydrogenative coupling of P(O)−H compounds with O-/S-nucleophiles to construct P−O bonds and P−S bonds for the synthesis of phosphinates and phosphinothioates was developed. A broad range of O- and S-nucleophiles are well tolerated in this transformation, affording the target products with good to excellent yields. This protocol is effective and convenient, which not only

  开发了铜催化的 P(O)-H 化合物与 O-/S-亲核试剂的交叉脱氢偶联以构建用于合成次膦酸盐和硫代膦酸盐的 P-O 键和 P-S 键。在这种转化中，广泛的 O- 和 S- 亲核试剂具有良好的耐受性，为目标产物提供了良好的收率。该方案既有效又方便，不仅采用廉价的碘化铜作为催化剂，而且避免了有害和有毒试剂的使用。通过逐步控制实验和竞争实验，我们提出了一个似是而非的反应机理，并进一步证实了该反应可能遵循自由基过程。
• Metal-Free Visible-Light-Mediated Oxidative Cross-Coupling of Thiols with P(O)H Compounds Using Air as the Oxidant
  作者：Jian-Guo Sun、Hua Yang、Ping Li、Bo Zhang

  DOI：10.1021/acs.orglett.6b02563

  日期：2016.10.7

  Visible light along with 5 mol % of rose bengal, catalyzes the direct S-P(O) coupling between thiols and P(O) H compounds in the presence of air as the green oxidant. The, protocol is operationally simple and amenable to gram-scale synthesis. A variety of S-P(O) coupling products can be readily. prepared in moderate to excellent yields. The reaction features good functional-group tolerance, operational simplicity, and excellent practicality.