Beta-cyano phosphoryl derivatives as well as preparation method and application thereof
A technology of cyanophosphono and derivatives, which is applied in the field of preparation of organic compounds, can solve the problems of harsh reaction conditions, difficult to obtain raw materials, and many reaction steps, and achieve the effects of short reaction time, overcoming toxicity, and simple steps
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[0038] Example 1: Synthesis of 2-phenyl-3-diphenoxyphosphinopropionitrile
[0039] Using styrene and diphenylphosphine oxide as raw materials, the reaction steps are as follows:
[0040] Add styrene (0.042 g, 0.4 mmol), diphenoxy phosphine (0.081 g, 0.4 mmol), trimethylcyanosilane (0.040 g, 0.4 mmol), CuCl (0.04g, 0.04 mmol) into the reaction flask, Manganese acetate (0.322 g, 1.2 mmol) and toluene (3 mL) were reacted at 100°C under argon protection;
[0041] TLC tracks the reaction until it is completely over;
[0042] After the reaction, the crude product obtained was separated by column chromatography (ethyl acetate: petroleum ether = 1:1) to obtain the target product (yield 73%). The analytical data of the product is as follows: 1 H NMR (400 MHz, CDCl 3 ): δ 7.92 – 7.81 (m, 2H),7.77 – 7.69 (m, 2H), 7.58 – 7.48 (m, 4H), 7.46 – 7.37 (m, 4H), 7.33 – 7.23(m, 3H), 4.39 (td, J = 9.4, 5.8 Hz, 1H), 3.12 – 2.94 (m, 1H), 2.95 – 2.56 (m, 1H).
Example Embodiment
[0043] Example 2: Synthesis of 2-(4-methylphenyl)-3-diphenoxyphosphinylpropionitrile
[0044] Using 4-methylstyrene and diphenylphosphine oxide as raw materials, the reaction steps are as follows:
[0045] Add 4-methylstyrene (0.047 g, 0.4 mmol), diphenoxy phosphine (0.081 g, 0.4 mmol), trimethylcyanosilane (0.040 g, 0.4 mmol), CuCl (0.04g, 0.04 mmol), manganese acetate (0.322 g, 1.2 mmol) and toluene (3 mL), react at 90°C under argon protection;
[0046] TLC tracks the reaction until it is completely over;
[0047] After the reaction, the crude product obtained was separated by column chromatography (ethyl acetate: petroleum ether = 1:1) to obtain the target product (yield 72%). The analytical data of the product is as follows: 1 H NMR (400 MHz, CDCl 3 ): δ 7.79 (dd, J = 10.7,7.8 Hz, 2H), 7.62 – 7.48 (m, 5H), 7.45 (t, J = 7.3 Hz, 1H), 7.35 (t, J = 6.6Hz, 2H), 7.18 (d, J = 7.8 Hz, 2H), 7.02 (d, J = 7.6 Hz, 2H), 4.41 (d, J = 6.6Hz, 1H), 3.01 (dt, J = 15.0, 7.6 Hz, 1H), 2.7...
Example Embodiment
[0048] Example 3: Synthesis of 2-(4-methoxyphenyl)-3-diphenoxyphosphinylpropionitrile
[0049] Using 4-methoxystyrene and diphenylphosphine oxide as raw materials, the reaction steps are as follows:
[0050] Add 4-methoxystyrene (0.054 g, 0.4 mmol), diphenoxy phosphine (0.162 g, 0.8 mmol), trimethylcyanosilane (0.040 g, 0.4 mmol), CuCl (0.04g) to the reaction flask , 0.04 mmol), manganese acetate (0.322 g, 1.2 mmol) and N,N-dimethylformamide (3 mL), react under argon protection at 80°C;
[0051] TLC tracks the reaction until it is completely over;
[0052] After the reaction, the crude product obtained was separated by column chromatography (ethyl acetate: petroleum ether = 1:1) to obtain the target product (yield 70%). The analytical data of the product is as follows: 1 H NMR (400 MHz, CDCl 3 ): δ 7.78 (s, 2H), 7.63 --7.49 (m, 5H), 7.43 (s, 1H), 7.35 (s, 2H), 7.21 (s, 2H), 6.72 (s, 2H), 4.42(s, 1H) , 3.73 (s, 3H), 3.03 (s, 1H), 2.80 (s, 1H).
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