O-methyl phenylphosphinothioate | 88044-05-7

• 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-methyl phenylphosphinothioate
• 英文别名: methyl phenylthiophosphinate；Methoxy-phenyl-sulfidophosphanium；methoxy-phenyl-sulfidophosphanium
• CAS: 88044-05-7
• 化学式: C₇H₉OPS
• 分子量: 172.188
• InChiKey: QSVVGDQZQMGWDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  235.5±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  10.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-methyl phenylphosphinothioate 在 二叔丁基过氧化物 作用下， 以 正戊烷 为溶剂， 生成
  参考文献：
  名称：

  ESR spectra of phosphonylthio-substituted ethyl radicals

  摘要：

  DOI：

  10.1007/bf00954075
• 作为产物：
  描述：

  苯膦酸 在 劳森试剂 、 吡啶 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.75h， 生成 O-methyl phenylphosphinothioate
  参考文献：
  名称：

  N-甲氧基吡啶鎓甲苯磺酸盐的亲核芳香取代合成2-吡啶基次膦酸盐和硫代次膦酸盐衍生物

  摘要：

  我们开发了一种基于 N-甲氧基吡啶鎓盐的亲核芳族取代合成 2-吡啶基次膦酸酯衍生物的简单且经济有效的方法。方法...

  DOI：

  10.1246/cl.2012.1630

文献信息

• Synthesis of 2-pyridylthiophosphinic acids and 2-pyridylthiophosphonate monoesters via nucleophilic aromatic substitution
  作者：Natsuhisa Oka、Kensuke Ori、Kaori Ando

  DOI：10.1080/10426507.2016.1248763

  日期：2017.4.3

  were converted into N-methoxypyridinium sulfonates, which were then used for nucleophilic aromatic substitution with the H-thiophosphinate/thiophosphonate esters to afford 2-pyridylthiophosphinate monoesters and 2-pyridylthiophosphonate diesters. Finally, alkaline hydrolysis and subsequent neutralization afforded various 2-pyridylthiophosphinic acids and 2-pyridylthiophosphonate monoesters in good yields

  图形摘要 在本研究中，我们开发了一种合成 2-吡啶硫代次膦酸和 2-吡啶硫代膦酸单酯的方法，该方法使用容易获得的原料 H-次膦酸酯和 H-膦酸酯以及吡啶 N-氧化物。H-次膦酸酯和H-膦酸酯被硫化，得到H-硫代次膦酸酯和H-硫代膦酸酯。吡啶N-氧化物转化为N-甲氧基吡啶鎓磺酸盐，然后将其用于与H-硫代次膦酸酯/硫代膦酸酯的亲核芳族取代，以提供2-吡啶硫代次膦酸单酯和2-吡啶硫代膦酸二酯。最后，碱水解和随后的中和以良好的产率提供了各种 2-吡啶基硫代次膦酸和 2-吡啶基硫代膦酸单酯。
• Synthesis and photochemical reaction of diels-alder adduct of phosphole oxide and cyclopentadiene
  作者：Hideo Tomioka、Shinichi Miura、Yasuji Izawa

  DOI：10.1016/s0040-4039(00)86268-1

  日期：——

  Irradiation of 1-phenylphosphole oxide-cyclopentadiene adduct gave a caged product, whereas similar irradiation of 1,2,5-triphenylphosphole oxide-cyclopentadiene adduct afforded a cleavaged product.

  辐照1-苯基氧化膦-环戊二烯加合物得到了笼状产物，而类似的1,2,5-三苯基氧化膦-环戊二烯加合物的辐照得到了裂解产物。
• Copper(I)-catalyzed diastereodivergent construction of vicinal P-chiral and C-chiral centers facilitated by dual “soft-soft” interaction
  作者：Yan-Bo Li、Yi Li、Liang Yin

  DOI：10.1016/j.cclet.2023.109294

  日期：2024.7

  present reaction. The first “soft-soft” interaction between copper(I) catalyst and HP(S)ROR' enables facile deprotonation to generate nucleophilic [Cu]-SPROR' species. The second one between the [Cu]-SPROR' species and -unsaturated thioamides facilitated the nucleophilic addition. Finally, both Michael adducts and ()-HP(S)PhOMe are easily converted to synthetically useful compounds.

  公开了铜(I)催化的硫代膦酸酯(HP(S)ROR')与不饱和硫代酰胺的非对映发散加成，其以通常高的非对映选择性和对映选择性构建邻位手性和手性中心。在该反应中，发生HP(S)ROR'的动力学拆分，以()-Ph-BPE作为配体加成，得到高对映选择性的()-HP(S)PhOMe。通过对照实验发现，H和P NMR实验表明的双重“软-软”相互作用在本反应中是不可或缺的。铜(I)催化剂和HP(S)ROR'之间的首次“软-软”相互作用能够轻松去质子化，生成亲核[Cu]-SPROR'物质。 [Cu]-SPROR'物质和-不饱和硫代酰胺之间的第二种促进了亲核加成。最后，迈克尔加合物和 ()-HP(S)PhOMe 都很容易转化为合成上有用的化合物。
• Experiments on the generation of 2-coordinate phosphoryl species by fragmentation of 7-phosphanorbornene and 3-phospholene derivatives
  作者：Louis D. Quin、Stefan Jankowski、Juliusz Rudzinski、Anthony G. Sommese、Xiao Ping Wu

  DOI：10.1021/jo00075a014

  日期：1993.11

  2,6-Di-tert-butyl-4-methylphenylphosphenite (ArOP=O) was released into the gas phase on heating a neat sample of a 7-phosphanorbornene derivative 6 bearing this aryloxy substituent at 300-degrees-C (0.01 mm). Attempts to prepare 1-adamantyl phosphenite similarly were not successful. Irradiation of 6 in 1,2-dichloroethane at 254 nm failed to cause release of the phosphenite, but when some alcohol was present fragmentation proceeded readily to give the H-phosphonate (ArOPH(O)OR). It was deduced that the species undergoing the fragmentation was a 5-coordinate adduct of 6 and the alcohol. Similar behavior was observed for the other esters and also for a P-phenyl oxide and a P-phenyl sulfide in the 7-phosphanorbornene series, as well as for a 3-phospholene oxide. Isotope exchange experiments with (OH2)-O-18 proved the influence of the irradiation on the formation and fragmentation of the 5-coordinate adduct. Earlier literature reports that 2-coordinate species are released on irradiation of 7-phosphanorbornene and 3-phospholene derivatives therefore need reinterpretation.
• Hussong, Rita; Heydt, Heinrich; Regitz, Manfred, Phosphorus and Sulfur and the Related Elements, 1985, vol. 25, p. 201 - 212
  作者：Hussong, Rita、Heydt, Heinrich、Regitz, Manfred

  DOI：——

  日期：——