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Polysubstituted silacyclohexadiene and synthetic method thereof

A silacyclohexadiene, multi-substituted technology, which is applied in chemical instruments and methods, compounds of Group 4/14 elements of the periodic table, organic chemistry, etc., can solve problems such as application research, and achieve high separation yields , convenient for industrialization, and the effect of a wide range of applications

Inactive Publication Date: 2008-10-15
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For silacyclohexadiene, which has similar stability to silacyclopentadiene, its general synthetic method has not been reported at present, and there is no related application research.

Method used

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  • Polysubstituted silacyclohexadiene and synthetic method thereof
  • Polysubstituted silacyclohexadiene and synthetic method thereof
  • Polysubstituted silacyclohexadiene and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Ia(R 1 = R 2 = Me,R 3 =COOMe,R 4 = Ph, R 5 = H, R 6 =Ph): Synthesis of (4Z)-methyl 4-benzylidene-1,4-dihydro-1,1-dimethyl-6-phenyl-silacyclohexadiene-3-carbonate

[0035] Add 1 mmol of polysubstituted silacyclobutene IIa (R 1 = R 2 = Me,R 4 = Ph, R 5 = H, R 6 =Ph)[(2Z)-2-benzylidene-1,2-dihydro-1,1-dimethyl-4-phenylsilacyclobutene], 1 mmol propiolate, 1% equivalent Pd(PPh 3 ) 4 and 5mL of toluene solvent, heated to reflux, and magnetically stirred for 3 hours. Concentrate after the reaction, decolorize and separate on a silica gel column, and use a mixed solvent of petroleum ether: ether = 10:1 as eluent to obtain the pure product (4Z)-methyl 4-benzylidene-1,4-dihydro-1, 1-Dimethyl-6-phenyl-silacyclohexadiene-3-carbonate 0.315 g (purity>98%, colorless liquid), isolated yield 91%. The NMR, IR and high-resolution mass spectrometry data of the compound are as follows: 1 H NMR (300MHz, CDCl 3 , Me 4 Si): δ=0.35(s, 6H), 3.09(s, 3H), 6.98(s, 1H), 7.23-7.36(m,...

Embodiment 2

[0037] Ib(R 1 = R 2 = Ph, R 3 =COOMe,R 4 = Ph, R 5 = H, R 6 =Ph) synthesis:

[0038] Add 1 mmol of polysubstituted silacyclobutene IIb (R 1 = R 2 = Ph, R 4 = Ph, R 5 = H, R 6 =Ph), 1 mmol propiolate, 1% equivalent of Pd (PPh 3 ) 4 and 5mL of toluene solvent, heated to reflux, and magnetically stirred for 3 hours. Concentrate after the reaction, decolorize and separate on a silica gel column, and use a mixed solvent of petroleum ether: ether=10:1 as an eluent to obtain the pure product multi-substituted silacyclohexadiene Ib (R 1 = R 2 = Me,R 3 =COOMe,R 4 = Ph, R 5 =H) 0.418 g (purity>98%, colorless liquid), isolated yield 89%. The NMR, IR and high-resolution mass spectrometry data of the compound are as follows: 1 H NMR (CDCl 3 , Me 4 Si): δ=3.10(s, 3H, CH 3 ), 7.16-7.58 (m, 23H, CH); 13 C NMR (CDCl 3 , Me 4 Si): δ=51.6, 126.8, 127.1, 128.1, 128.2, 128.3, 128.5, 129.1, 123.0, 133.2, 133.5, 135.4, 135.7, 137.6, 137.7, 140.6, 142.7, 145.8, 147.3, 168.6: I...

Embodiment 3

[0040] Ic(R 1 = R 2 = Me,R 3 = COPh,R 4 = Ph, R 5 = H, R 6 =Ph): Synthesis of ((4Z)-4-benzylidene-1,4-dihydro-1,1-dimethyl-6-phenylsilacyclohexadien-3-yl)benzophenone

[0041] Add 1 mmol of polysubstituted silacyclobutene IIc (R 1 = R 2 = Me,R 4 = Ph, R 5 = H, R 6 =Ph)[(2Z)-1,2-dihydro-1,1-dimethyl-4-phenyl-2-((E)-1-phenyl-2-propylhex-2-enyl Methylene) silacyclobutene], 1.5 mmol alkynyl benzophenone, 1% equivalent of Pd (PPh 3 ) 4 and 5mL of toluene solvent, heated to reflux, and magnetically stirred for 1 hour. Concentration after the reaction, decolorization and separation on a silica gel column, using a mixed solvent of petroleum ether: ether = 10: 1 as eluent, the obtained pure product ((4Z)-4-benzylidene-1,4-dihydro-1, 0.274 g of 1-dimethyl-6-phenylsilacyclohexadien-3-yl)benzophenone (purity>98%, colorless solid), isolated yield 70%. The NMR and IR high-resolution mass spectrometry data of the compound are as follows: 1 H NMR (300MHz, CDCl 3 , Me 4 Si): δ...

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Abstract

The invention provides polysubstituted silicon heterocyclic hexadiene as shown in formula I, wherein R<1> and R<2> are identical or different and represent alkyl or aryl; R<3> represents hydrogen, aldehyde group, ketone group, ester group and phosphate group; R<4> represents alkyl and aryl; R<5> represents hydrogen, alkyl, alkenyl and aryl; and R<6> represents alkyl and aryl. The compound which has high molecular stability is an important precursor of organic conducting material and organic photoelectric material. The invention adopts the insertion ring-enlargement reaction between end group alkyne and silicon heterocyclic butane under the catalysis of palladium to make the polysubstituted silicon heterocyclic hexadiene at high yield. The method, being scientific and reasonable, has easily obtained raw material, wide application range, high separation yield and simple experimental equipment and operation, and is convenient for industrial production.

Description

technical field [0001] The invention belongs to the field of organic conductive materials and photoelectric materials, in particular to a compound with a multi-substituent silacyclohexadiene structure and a general synthesis method thereof. Background technique [0002] Planar conjugated organosilicon compounds, due to the special effect of silicon atoms on organic conjugated systems, have excellent electronic and photoelectric physical properties, and can be used as precursors of organic conductive materials and organic photoelectric materials. The current research on planar conjugated organosilicon molecules is limited to silacyclobutene [such as: the compound shown in formula A (US Pat.Appl.874469, 16 Jul.1997) and the compound shown in formula B (Can. Pat.Appl.645666, 30 May 1991)] and silacyclopentadiene [a compound represented by formula C (J.Am.Chem.Soc.1999, 121, 10420-10421)]. For silacyclobutene, due to its low stability, its application research is very limited; ...

Claims

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Application Information

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IPC IPC(8): C07F7/18
Inventor 席振峰刘俊辉
Owner PEKING UNIV
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