Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of diaryl methyl phosphorous oxygen compound and its synthetic method

A technology of diarylmethylphosphorus and arylmethylphosphorus, which is applied in the field of diarylmethylphosphorus oxide and its synthesis, and can solve problems such as complex operation, non-environmental friendliness, and limited range of phosphorus oxide , to achieve the effects of environmental friendliness, good substrate universality, and simple reaction operation

Active Publication Date: 2021-08-17
LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In view of this, the present invention provides a kind of diaryl methyl phosphorus oxy compound and its synthesis method, to at least solve the previous method of synthesizing diaryl methyl phosphorus oxy compound, there are catalysts and ligands synthesis complex, phosphorus oxy compound range Limited, non-market economical, non-environmentally friendly, and complicated to operate

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of diaryl methyl phosphorous oxygen compound and its synthetic method
  • A kind of diaryl methyl phosphorous oxygen compound and its synthetic method
  • A kind of diaryl methyl phosphorous oxygen compound and its synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064]

[0065] The reactor was placed in air, and 0.2mmol (56.8mg) p-methylene quinone compound (1a), 0.3mmol (60.6mg) diphenylphosphine oxy compound (2a), 0.04mmol (6.1mg) DBU were added successively, 1 mL of DCM, stirred at 40°C for 4h. After the reaction was completed, the solvent was adjusted with a rotary evaporator, and the crude product was subjected to column chromatography, and the eluent was a mixed solvent of petroleum ether and ethyl acetate to obtain 49.6 mg of diarylmethylphosphoryl oxide 3aa, with an isolated yield of 51%. .

[0066] see Figure 1 ~ Figure 3 , the characterization data of compound 3aa are as follows:

[0067] 1 H NMR (400MHz, CDCl 3 )δ7.79-7.74(m,2H),7.49-7.36(m,6H),7.29-7.24(m,3H),6.93(d,J=2.0Hz,2H),6.51(t,J=2.6Hz ,1H),6.25(dd,J=3.6,2.0Hz,1H),5.11(s,1H),4.87(d,J=12.8Hz,1H),1.29(s,18H). 13 C NMR (100MHz, CDCl 3 )δ153.1(d, J=2.9Hz), 150.1(d, J=1.4Hz), 141.6(d, J=1.9Hz), 135.5(d, J=2.3Hz), 132.4(d, J=33.7 Hz), 131.7(d, J=2.7Hz), 131.6(...

Embodiment 2

[0069]

[0070] The reactor was placed in the air, and 0.2mmol (64.4mg) p-methylene quinone compound (1b), 0.3mmol (60.6mg) diphenylphosphine oxy compound (2a), 0.04mmol (6.1mg) DBU, 1 mL of DCM, stirred at 40°C for 4h. After the reaction was completed, the solvent was adjusted with a rotary evaporator, and the crude product was subjected to column chromatography, and the eluent was a mixed solvent of petroleum ether and ethyl acetate to obtain 94.4 mg of diarylmethylphosphoryl oxide 3ba, and the separation yield was 90%. .

[0071] see Figure 4 ~ Figure 6 , the characterization data of compound 3ba are as follows:

[0072] 1 H NMR (400MHz, CDCl 3 )δ7.75-7.70(m,2H),7.46-7.33(m,7H),7.27-7.23(m,3H),7.07(d,J=2.0Hz,2H),6.97(d,J=7.6Hz ,1H),5.01(s,1H),4.58(d,J=10.0Hz,1H),2.15(s,3H),2.14(s,3H),1.29(s,18H). 13 C NMR (100MHz, CDCl 3 )δ152.6(d, J=2.5Hz), 136.5, 135.3(d, J=1.6Hz), 135.0(d, J=4.1Hz), 134.9(d, J=1.3Hz), 133.5(d, J =67.2Hz), 132.6(d, J=64.4Hz), 131.6(d, J=8.4Hz)...

Embodiment 3

[0074]

[0075] The reactor was placed in air, and 0.2mmol (42.0mg) p-methylene quinone compound (1c), 0.3mmol (60.6mg) diphenylphosphine oxy compound (2a), 0.04mmol (6.1mg) DBU, 1 mL of DCM, stirred at 40°C for 4h. After the reaction was completed, the solvent was adjusted with a rotary evaporator, and the crude product was subjected to column chromatography, and the eluent was a mixed solvent of petroleum ether and ethyl acetate to obtain 76.6 mg of diarylmethylphosphoryl oxide 3ca, and the separation yield was 93%. .

[0076] see Figure 7 ~ Figure 9 , the characterization data of compound 3ca are as follows:

[0077] 1 H NMR (400MHz, CDCl 3 )δ7.63-7.55(m,4H),7.42(d,J=7.2Hz,2H),7.34(t,J=6.4Hz,2H),7.29-7.24(m,4H),7.13-7.08(m ,3H),7.04(s,2H),5.98(s,1H),4.64(d,J=9.2Hz,1H),2.09(s,6H). 13 C NMR (100MHz, CDCl 3 )δ151.8(d, J=1.8Hz), 137.6(d, J=4.2Hz), 133.1, 132.1(d, J=1.5Hz), 131.5, 131.4(d, J=2.8Hz), 131.3(d ,J=2.6Hz),131.2129.9(d,J=7.3Hz),129.8(d,J=7.2Hz),128.4,128.2...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a diarylmethyl phosphorus oxy compound and a synthesis method thereof. The synthesis method uses a simple and easy-to-obtain base as a catalyst, p-methylene quinone and a phosphorus oxy compound as a substrate, and a one-step efficient Realize the construction of C-P bonds and synthesize diarylphosphorus oxide compounds; the above synthesis method has the advantages of good substrate universality, cheap and easy-to-obtain catalyst, simple reaction operation, and environmental friendliness. Synthesized using the above method.

Description

technical field [0001] The disclosure of the invention relates to the technical field of organic synthetic chemistry, in particular to a diarylmethylphosphoryl oxide compound and a synthesis method thereof. Background technique [0002] Organophosphine compounds are a class of valuable compounds, which widely exist in pesticides, medicines and other natural products, and some organophosphine compounds can be used as metal ligands, and have a wide range of applications in organometallic chemistry. In recent years, with the rapid development of carbon-hydrogen bond activation, it is of great research significance to introduce phosphorus atoms into substrates and synthesize organophosphine compounds in a simple, efficient and green way. In particular, using phosphorus oxycompounds, such as diarylphosphoryloxycompounds and phosphite compounds, as coupling components to realize the construction of C-P bonds in one step is a research hotspot in organic chemistry in recent years. ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/655C07F9/53C07F9/40
Inventor 李蕾宫清嵩王贺周明东
Owner LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY