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Silca bridged cycloalkene compounds and preparation method and use thereof

A technology for silacyclopentene and compounds, which is applied in the field of important organic synthesis intermediates, can solve the problems of no literature reports and no synthesis methods in the research of silacyclopentene, and achieve simple, feasible and applicable scope of experimental equipment and operation The effect of wide and easy-to-obtain raw materials

Active Publication Date: 2014-07-16
江苏肇方智能装备有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Silacyclopentene is a novel compound. Since 1959, Japanese scholar Brave (Braye EH, Hubel W.Chem.Ind. (Lond.), 1959: 1250-1251) synthesized silacyclopentadiene. , the research on silacyclopentadiene derivatives continues to appear, but there is no literature report on the research on silacyclopentadienes, and there is no general synthetic method

Method used

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  • Silca bridged cycloalkene compounds and preparation method and use thereof
  • Silca bridged cycloalkene compounds and preparation method and use thereof
  • Silca bridged cycloalkene compounds and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1: Preparation of 1,1 dialkyl(aryl)yl-3,4-diphenyl-2,5-dilithium silole.

[0053] Taking 1,1 dimethyl-3,4-diphenyl-2,5-dilithium silole as an example, prepared according to the method disclosed in the literature (J AmChem Soc, 1994, 116:11715211722.), under the protection of nitrogen Next, in a 50ml reaction flask, lithium metal (0.14g, 0.02mol) was reacted with naphthalene (2.56g, 0.02mol) dissolved in 12mlTHF at room temperature for 3 hours. Add dropwise dimethyldiphenylethynylsilane (1.30 g, 0.005 mol) dissolved in 5 ml THF to the above solution, and react for 1 hour to generate 1,1 dimethyl-3,4-diphenyl-2,5 - Dilithium silole. It was directly used in the next reaction without separation.

Embodiment 2

[0054] Example 2: Preparation of 1,1-dimethyl-3,4-diphenyl-2,2,5,5-tetrakis(dimethylsilyl)yl-3-silacyclopentene.

[0055]

[0056] R 1

R 2

R 3

R 4

R 5

Methyl

Methyl

Methyl

Methyl

---

[0057] At room temperature, under the protection of nitrogen, metal lithium (0.28g, 0.04mol) reacted with naphthalene (5.12g, 0.04mol) dissolved in 24mlTHF for 3 hours at room temperature, and then added 2.6g of dimethyl dissolved in 10mlTHF Diphenylethynylsilane (0.01mol), reacted for 1 hour to obtain a reaction solution containing 0.01mol 1,1-dimethyl-3,4-diphenyl-2,5-dilithium silole, and then added 4.0ml Dimethylchlorosilane (0.04mol), reacted for 10 hours, extracted the aqueous phase with 25ml ether three times after the reaction was completed, combined the organic phases, washed with saturated sodium chloride solution, and washed with anhydrous MgSO 4 Dry for half an hour, filter under normal pressure, concentrate the f...

Embodiment 3

[0061] Example 3: Preparation of 1,1,3,4-tetraphenyl-2,2,5,5-tetrakis(methylphenylsilyl)yl-3-silacyclopentene.

[0062]

[0063] R 1

R 2

R 3

R 4

R 5

Phenyl

Phenyl

Methyl

Phenyl

---

[0064] At 25°C, under the protection of nitrogen, metal lithium (0.28g, 0.04mol) reacted with naphthalene (5.12g, 0.04mol) dissolved in 24mlTHF for 3 hours at room temperature, and then added 3.92g diphenyl diphenylene dissolved in 10mlTHF Diphenylethynylsilane (0.01mol), reacted for 1 hour to prepare a reaction solution containing 0.01mol 1,1,3,4-tetraphenyl 2,5-dilithium silole, and then added 5.0ml methylbenzene Chlorochlorosilane (0.05mol), reacted for 10 hours, extracted the aqueous phase three times with 25ml ether after the reaction was completed, combined the organic phases, washed with saturated sodium chloride solution, and dried for half an hour with anhydrous MgSO4 after liquid separation, filtered under normal press...

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Abstract

The invention discloses silca bridged cycloalkene compounds of formula (I) and discloses a preparation method of the silca bridged cycloalkene compounds and the use of the silca bridged cycloalkene compounds as luminescent materials.

Description

(1) Technical field [0001] The invention relates to a silicon heterobridged cycloalkene compound and a synthesis method thereof, belonging to important organic synthesis intermediates. (2) Background technology [0002] Silacyclopentene is a novel compound. Since 1959, Japanese scholar Brave (Braye EH, Hubel W.Chem.Ind. (Lond.), 1959: 1250-1251) synthesized silacyclopentadiene. , research on silacyclopentadiene derivatives continues to appear, but there is no literature report on the research on silacyclopentadiene derivatives, and there is no general synthetic method. (3) Contents of the invention [0003] The object of the present invention is to provide a series of sila bridged cycloalkene compounds. [0004] Another object of the present invention is to provide a method for synthesizing sila-bridged cycloalkenes. [0005] The sila bridged cycloalkene compound provided by the present invention is shown in formula I: [0006] [0007] In formula I, [0008] R 1 ,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/08C09K11/06
Inventor 邱化玉郭延举冯海柯赵祖金尹守春
Owner 江苏肇方智能装备有限公司
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