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Preparation method of beta-trifluoromethyl thiophosphate compound
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A technology of trifluoromethyl thiophosphate and trifluoromethylation, which is applied in the field of preparation of β-trifluoromethyl thiophosphate compounds, can solve the problem that the substrate is limited, the synthesis of thiophosphate is difficult, and the problems such as low atomic economy, to achieve the effect of easy availability of raw materials, cheap raw materials, and good atomic economy
Pending Publication Date: 2021-08-17
XINXIANG MEDICAL UNIV
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[0004] The present invention provides a β-trifluoromethyl phosphorothioate compound in order to overcome the disadvantages of trifluoromethyl-substituted phosphorothioate in the prior art, such as high difficulty in synthesis, large substrate restriction, and low atom economy. The preparation method of the present invention has low reaction cost, mild reaction conditions, good atom economy, high selectivity, high yield, simple and easy control of the reaction process, and is suitable for industrial production
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Embodiment 1
[0028]
[0029] Anhydrouscopper acetate (5.5 mg, 0.03 mmol), 1,10-phenanthroline monohydrate (11.9 mg, 0.06 mmol), sulfurpowder (19.2 mg, 0.6 mmol) and dichloromethane were sequentially added to a 10 mL Schlenk bottleSolvent (2mL), then added H-diethyl phosphite (82.8mg, 0.6mmol), triethylamine (60.6mg, 0.6mmol), stoppered and stirred at room temperature for half an hour, opened the stopper and added styrene 1a (31.2mg , 0.3mmol), Togni II (31.2mg, 0.6mmol), through argon for 30s, stoppered and continue to react at room temperature for 8h, extracted with 2x8 mL ethyl acetate, combined organic phases, dried over anhydroussodiumsulfate, filtered After spin-drying, a mixed solvent of petroleumether and ethyl acetate with a volume ratio of 3:1 was used to pass through the column to obtain 92.3 mg of the target compound (compound 3a), with a yield of 90%. Yield: 92.3mg, 90%; Colourless liquid; 1 H NMR (400MHz, CDCl 3 )δ7.37-7.27(m,5H),4.57-4.52(m,1H),4.13-3.93(m,3H),3.92...
Embodiment 2
[0031] The ligand 1,10-phenanthroline monohydrate was not added, and other conditions were the same as in Example 1. The yield of the target product 3a was 75%.
Embodiment 3
[0033]
[0034] Using 4-methylstyrene 1b (35.4mg, 0.3mmol) instead of styrene 1a as the raw material, the other conditions were the same as in Example 1 to obtain 87.6mg of the target compound (compound 3b) with a yield of 82%. 1 H NMR (400MHz, CDCl 3)δ7.26-7.22(m,2H),7.15-7.13(m,2H),4.54-4.48(m,1H),4.12-3.97(m,3H),3.93-3.83(m,1H),3.04- 2.90(m,1H),2.87-2.76(m,1H),2.32(s,3H),1.26(t,J=7.1Hz,3H),1.22(t,J=7.1Hz,3H). 13 C NMR (151MHz, CDCl 3 )δ138.3, 137.3(d, J=5.0Hz), 129.7, 127.4, 125.2(q, J=278.4Hz), 63.94(d, J=6.5Hz), 63.90(d, J=6.2Hz), 43.86-43.77 (m), 42.0(qd, J=28.0, 6.8Hz), 21.3, 16.03(d, J=6.9Hz), 15.98(d, J=6.8Hz). 31 P NMR (243MHz, CDCl 3 )δ23.94. 19 F NMR (471MHz, CDCl 3 ) δ-63.78.
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Abstract
The invention discloses a preparation method of a beta-trifluoromethylthiophosphate compound, and belongs to the technical field of synthesis of thiophosphate compounds in organic synthesis. According to the technical scheme, the preparation method of the beta-trifluoromethylthiophosphate compound is characterized by comprising the following specific steps: in the presence of a catalyst and alkali, taking a trifluoromethylationreagent, powdered sulfur, hydrogen phosphite or hydrogen phosphite and an olefin compound as reaction substrates in an organic solvent, and reacting at 0-100 DEG C to obtain the target product beta-trifluoromethyl thiophosphate compound. The preparation method provided by the invention has the advantages of low reaction cost, mild reaction conditions, good atom economy, high selectivity, high yield and simple and easily-controlled reaction process, and is suitable for industrial production.
Description
technical field [0001] The invention belongs to the technical field of synthesis of phosphorothioate compounds in organic synthesis, and in particular relates to a preparation method of β-trifluoromethyl phosphorothioate compounds. Background technique [0002] Phosphorothioate is an important class of organophosphorus compounds. It has rich biological activity and special reactivity. It has a very wide range of applications in the fields of agriculture, medicine and organic synthesis. Representative drugs that have been marketed include Demeton-S( demeton-S), iprobenfos, malathion, dimethoate, amifostine, echothiophate, etc. On the other hand, trifluoromethyl has the advantages of strong electronegativity, high stability and good fat solubility, etc. Doping trifluoromethyl into organic molecules can significantly adjust its physiological activity, and it is increasingly used in the development of new drugs. more attention. However, the synthesis methods of trifluoromethyl...
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