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A kind of double silicon compound, its preparation method and application

A technology for silicon compounds and silanes, which is applied to organic silicon compounds, chemical instruments and methods, and compounds of elements of Group 4/14 of the periodic table. , good substrate universality, good tolerability effect

Active Publication Date: 2021-12-03
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Organosilicon compounds are not only used as special materials in aviation, technology, and military technology departments, but also in various sectors of the national economy. , metals and paints, medicine and medical treatment, etc. [a) Ojima, I.; Li, Z.; Zhu, J. The chemistry of organosilicon compounds; Rappoport, S., Apeloig, Y., Eds.; Wiley: New York, 1998. b) Langkopf, E.; Schinzer, D. Uses of silicon-containing compounds in the synthesis of natural products. Chem. Rev. 1995, 95, 1375-1408.] As a monomer of organosilicon materials, organosilicon containing silicon hydrogen The synthesis and application of small molecules is a very important research direction. Mater.2014,26,763-772.c)L.V.Interrante,Q.Shen in Silicon-Containing Polymers(Eds.:R.G.Jones,W.Ando,J.Chojnowski),Kluwer,Dordrecht,2000,pp.247-321.Currently , there are not many methods for synthesizing bisilicon compounds, and most of them are limited to the synthesis of symmetrical bisilicon compounds, but there are few reports on the synthesis of asymmetric bisilicon compounds.

Method used

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  • A kind of double silicon compound, its preparation method and application
  • A kind of double silicon compound, its preparation method and application
  • A kind of double silicon compound, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] Under the protection of inert gas, Ni(COD) was added to a dry 10.0mL reaction tube equipped with a magnetic stirrer 2 (5.5mg, 0.02mmol, 10mol%), (p-MeC 6 h 4 ) 3 P (12.2 mg, 0.04 mmol, 20 mol%), dried toluene (0.25 mL), A (29.6 mg, 0.2 mmol), diphenylsilane B (73.6 mg, 0.4 mmol, 2 equiv.). Seal the tube tightly and heat at 40°C for three hours. Then it was cooled to room temperature, and the reaction solution was suction-filtered with celite, and 30 ml of ethyl acetate was used as eluent. After the filtrate was spin-dried under reduced pressure, it was purified by a silica gel column, and the eluent was petroleum ether to obtain G1 (60 mg of colorless oily liquid, yield 90%). 1 H NMR (400MHz, CDCl 3 ,25℃)δ7.57–7.56(m,2H),7.56–7.54(m,2H),7.46–7.41(m,2H),7.40–7.35(m,4H),7.35–7.29(m,2H) ,7.15–7.10(m,1H),7.07(td,J=7.4,1.1Hz,1H),5.64(s,1H),3.92–3.86(m,1H),2.33(d,J=3.4Hz,2H ),0.02(d,J=3.7Hz,6H). 13 C NMR (101MHz, CDCl 3 ,25℃) δ147.4, 137.3, 136.1, 133.7, ...

Embodiment 3

[0038]

[0039] Under the protection of inert gas, Ni(COD) was added to a dry 10.0mL reaction tube equipped with a magnetic stirrer 2 (5.5mg, 0.02mmol, 10mol%), (p-MeC 6 h 4 ) 3 P (12.2mg, 0.04mmol, 20mol%), dry toluene (0.25mL), A (29.6mg, 0.2mmol), phenyl(m-fluorophenyl)silane B (80.8mg, 0.4mmol, 2equiv.). Seal the tube tightly and heat at 40°C for three hours. Then it was cooled to room temperature, and the reaction solution was suction-filtered with celite, and 30 ml of ethyl acetate was used as eluent. After the filtrate was spin-dried under reduced pressure, it was purified by a silica gel column, and the eluent was petroleum ether to obtain G3 (63 mg of colorless oily liquid, yield 90%). 1 H NMR (400MHz, CDCl 3 ,25℃)δ7.56–7.51(m,2H),7.47–7.42(m,1H),7.41–7.27(m,6H),7.24–7.20(m,1H),7.15–7.05(m,3H) ,5.63(s,1H),3.95–3.83(m,1H),2.31(d,J=3.4Hz,2H),0.02(d,J=3.7Hz,6H). 13 C NMR (101MHz, CDCl 3 ,25℃)δ162.79(d,J=248.6Hz),147.5,137.3,136.9(d,J=4.4Hz),136.0,132.9,131.7(d...

Embodiment 4

[0041]

[0042] Under the protection of inert gas, Ni(COD) was added to a dry 10.0mL reaction tube equipped with a magnetic stirrer 2 (5.5mg, 0.02mmol, 10mol%), (p-MeC 6 h 4 ) 3 P (12.2 mg, 0.04 mmol, 20 mol%), dry toluene (0.25 mL), A (29.6 mg, 0.2 mmol), phenyl (biphenyl) silane (104 mg, 0.4 mmol, 2 equiv.). Seal tightly Tubes were then heated at 40 °C for three hours. Then it was cooled to room temperature, and the reaction solution was suction-filtered with celite, and 30 ml of ethyl acetate was used as eluent. After the filtrate was spin-dried under reduced pressure, it was purified with a silica gel column, and the eluent was petroleum ether to obtain G6 (60 mg of colorless oily liquid, yield 74%). 1 H NMR (400MHz, CDCl 3 ,25℃)δ7.66–7.56(m,8H),7.50–7.30(m,8H),7.18–7.02(m,2H),5.68(s,1H),4.10–3.59(m,1H),2.36 (d,J=3.4Hz,2H),0.03(d,J=3.7Hz,6H). 13 C NMR (101MHz, CDCl 3 ,25℃).δ147.5,142.5,141.1,137.4,136.6,136.1,133.7,132.4,130.8,130.3,129.9,128.9,128.7,128.2,127.7...

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Abstract

The present invention relates to the technical field of organic synthesis, in particular to a double silicon compound, its preparation method and application. The molecular structure of the double silicon compound is as follows: wherein, R 1 , R 2 are aryl or alkyl, which can be the same or different; R 3 , R 4 , R 5 Any one of aryl group, alkyl group and hydrogen atom, which can be the same or different, R 3 , R 4 , R 5 Up to two hydrogen atoms at the same time, R 6 Any of aryl group, alkyl group, heteroatom and hydrogen atom. The preparation method of the present invention realizes the ring-opening metathesis reaction of four-membered ring silicon and silane, is a new reaction mode, and provides a simple and efficient method for synthesizing double silicon compounds, especially two silicons containing silicon hydrogen It can be used to synthesize polymers under circumstances, and has very great application prospects.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a double silicon compound, its preparation method and application. Background technique [0002] Organosilicon compounds are not only used as special materials in aviation, technology, and military technology departments, but also in various sectors of the national economy. , metals and paints, medicine and medical treatment, etc. [a) Ojima, I.; Li, Z.; Zhu, J. The chemistry of organosilicon compounds; Rappoport, S., Apeloig, Y., Eds.; Wiley: New York, 1998. b) Langkopf, E.; Schinzer, D. Uses of silicon-containing compounds in the synthesis of natural products. Chem. Rev. 1995, 95, 1375-1408.] As a monomer of organosilicon materials, organosilicon containing silicon hydrogen The synthesis and application of small molecules is a very important research direction. Mater.2014,26,763-772.c)L.V.Interrante,Q.Shen in Silicon-Containing Polymers(Eds.:R.G.Jones,W.Ando,J.Chojno...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/08C07F7/12C07F7/10C07F7/18
CPCC07F7/0807C07F7/0836C07F7/0838C07F7/0874C07F7/0896C07F7/12C07F7/126C07F7/1804C07F7/1888
Inventor 沈晓陈绍维
Owner WUHAN UNIV
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