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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

Active Publication Date: 2017-02-22
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] However, there are many deficiencies in the existing disclosed synthetic methods of compounds, such as the difficulty in obtaining raw materials, harsh reaction conditions, many reaction steps, and high toxicity. Synthetic method is very important to prepare β-cyanophosphono derivatives

Method used

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  • Beta-cyano phosphoryl derivatives as well as preparation method and application thereof
  • Beta-cyano phosphoryl derivatives as well as preparation method and application thereof
  • Beta-cyano phosphoryl derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment one: the synthesis of 2-phenyl-3-diphenoxyphosphinylpropionitrile

[0039] Using styrene and diphenylphosphine oxide as raw materials, the reaction steps are as follows:

[0040] Add styrene (0.042 g, 0.4 mmol), diphenoxyphosphine (0.081 g, 0.4 mmol), trimethylcyanosilane (0.040 g, 0.4 mmol), CuCl (0.04 g, 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 the protection of argon;

[0041] TLC tracking reaction until complete completion;

[0042] The crude product obtained after the reaction was separated by column chromatography (ethyl acetate: petroleum ether = 1:1) to obtain the target product (yield 73%). The analytical data of the product are 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).

Embodiment 2

[0043] Example 2: Synthesis of 2-(4-tolyl)-3-diphenoxyphosphinylpropionitrile

[0044] With 4-methylstyrene, diphenylphosphine oxide as raw material, its reaction steps are as follows:

[0045] Add 4-methylstyrene (0.047 g, 0.4 mmol), diphenoxyphosphine (0.081 g, 0.4 mmol), trimethylcyanosilane (0.040 g, 0.4 mmol), CuCl (0.04 g, 0.04 mmol), manganese acetate (0.322 g, 1.2 mmol) and toluene (3 mL), under the protection of argon, react at 90°C;

[0046] TLC tracking reaction until complete completion;

[0047] The crude product obtained after the reaction was separated by column chromatography (ethyl acetate:petroleum ether=1:1) to obtain the target product (yield 72%). The analytical data of the product are 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...

Embodiment 3

[0048] Example 3: Synthesis of 2-(4-methoxyphenyl)-3-diphenoxyphosphinylpropionitrile

[0049] With 4-methoxystyrene and diphenylphosphine oxide as raw materials, the reaction steps are as follows:

[0050] Add 4-methoxystyrene (0.054 g, 0.4 mmol), diphenoxyphosphine (0.162 g, 0.8 mmol), trimethylcyanosilane (0.040 g, 0.4 mmol), CuCl (0.04 g , 0.04 mmol), manganese acetate (0.322 g, 1.2 mmol) and N,N-dimethylformamide (3 mL), react at 80°C under argon protection;

[0051] TLC tracking reaction until complete completion;

[0052] The crude product obtained after the reaction was separated by column chromatography (ethyl acetate:petroleum ether=1:1) to obtain the target product (yield 70%). The analytical data of the product are 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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Abstract

The invention discloses Beta-cyano phosphoryl derivatives as well as a preparation method and an application thereof. Alkene is used as an initiator, and raw materials are easy to obtain and wide in type; products prepared with the method are diversified in type and wide in application range, can be directly used and can be used for synthesizing organic phosphine flame retardants, drugs and extracting agents. Besides, the method adopts simple steps, has mild reaction conditions, causes low pollution and is suitable for industrial production, the yield of target products is high, and reaction operation and after-treatment process are simple.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic compounds, and in particular relates to a preparation method of β-cyanophosphono derivatives. Background technique [0002] Organic phosphine flame retardants have good flame retardant performance, have dual functions of flame retardant and plasticizing, and can replace halogenated flame retardants, so they have good development prospects. The mechanism of action of this type of flame retardant is that organic phosphine compounds are thermally decomposed to generate phosphorus-containing oxyacids. This acid can form a graphite-like coke layer on the surface of the substrate. The coke layer is flame-resistant, heat-insulating, oxygen-insulating, and Can suffocate combustion (Reference: Gong Changsheng, Zhu Lijun. Synthesis and application of phosphorus-based flame retardants. Chemical Technology Economics. 2002, 2:9; 2, Xu Jingjing, Hao Huijun, etc. Research progress of phosphorus-ba...

Claims

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Application Information

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IPC IPC(8): C07F9/38C07F9/40C07F9/53C07F9/572C07F9/58C07F9/655C07F9/6553
CPCC07F9/3817C07F9/4006C07F9/4056C07F9/5325C07F9/572C07F9/5728C07F9/58C07F9/65515C07F9/655345
Inventor 邹建平张沛之张令李建安
Owner SUZHOU UNIV
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