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3,7-disubstituted-trans-dicyclo[3,3,0] octane compound and its preparation and use

A compound, two-substituted technology, used in chemical instruments and methods, organic chemistry, instruments, etc.

Inactive Publication Date: 2006-03-15
石家庄永生华清液晶有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] So far, there is no single liquid crystal compound that can meet the performance requirements alone in display devices without being combined with other compounds.

Method used

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  • 3,7-disubstituted-trans-dicyclo[3,3,0] octane compound and its preparation and use
  • 3,7-disubstituted-trans-dicyclo[3,3,0] octane compound and its preparation and use
  • 3,7-disubstituted-trans-dicyclo[3,3,0] octane compound and its preparation and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] This example relates to the synthesis of the intermediate 7,7-ethylenedioxy-3-trans-bicyclo[3.3.0]octanone.

[0083] 1) Synthesis of trans-bicyclo[3.3.0]octane 3,7-dione

[0084] Add 5.3 g of NaOH and 95 ml of anhydrous methanol into a 250 ml Erlenmeyer flask, stir until the NaOH is completely dissolved, and filter to obtain a NaOH / anhydrous methanol solution. Add 22.5 grams of dimethyl acetone dicarboxylate in a 250 ml three-necked flask, N 2 Under protection, NaOH / anhydrous methanol solution was added with stirring, a white solid precipitated out, and heated to reflux until the solid dissolved. 9.4 ml of 40% glyoxal aqueous solution was added dropwise, and the addition was completed in 25 minutes, and a solid precipitated out, then heated to reflux for 10 minutes, cooled to room temperature, filtered to obtain a yellow solid, which was washed twice with 50 ml of cold methanol.

[0085] A solution of 21 ml of 37% hydrochloric acid and 60 ml of water and a yellow so...

Embodiment 2

[0090] Synthesis of 3,3-Ethylenedioxy-7-(3′,5′-difluorophenyl)-trans-bicyclo[3.3.0]octane

[0091] The reaction process is as follows:

[0092]

[0093]In the there-necked flask of 250 milliliters, add 3 grams of magnesium chips and 20 milliliters of anhydrous tetrahydrofuran, in the dropping funnel of 100 milliliters, add the solution of 22 grams of 3,5-difluorobromobenzene (99.7%) and 40 milliliters of anhydrous tetrahydrofuran, 5 mL of the solution was added dropwise to initiate the reaction. Slowly add the tetrahydrofuran solution dropwise, maintaining a slight reflux. After dropping, heat to reflux for 1 hour until almost all the magnesium chips disappear. A solution of 18 g of 7,7-ethylenedioxy-3-trans-bicyclo[3.3.0]octanone and 40 ml of tetrahydrofuran was added dropwise, and the mixture was refluxed for 2 hours. Cool down to about 0°C. Add 24 ml of 6M hydrochloric acid dropwise, control the temperature below 30°C, and hydrolyze for half an hour. Poured into wat...

Embodiment 3

[0125]

[0126] Synthesis of 3-oxo-7-(3′,4′-difluorophenyl)-trans-bicyclo[3.3.0]octane

[0127] Add 20 grams of 3,3-ethylenedioxy-7-(3',4'-difluorophenyl)-trans bicyclo[3.3.0]octane obtained in Example 2 to a 500-ml one-port bottle, 600 mL 88% formic acid, 200 mL toluene, stirred at room temperature for 12 hours, separated, washed the toluene layer with water until neutral, anhydrous Na 2 SO 4 Dry for 4 hours, filter and distill off the solvent to obtain 16.15 g of 3-oxo-7-(3',4'-difluorophenyl)-trans-bicyclo[3.3.0]octane, with a melting point of 44°C and a gas phase purity of 99.7 %.

[0128] The compound (b-n) that obtains with reference to above-mentioned same method hydrolysis embodiment 3 obtains following compound:

[0129] 3-Oxo-7-(3′,5′-difluorophenyl)-trans-bicyclo[3.3.0]octane

[0130]

[0131] 3-Oxo-7-(4′-fluorophenyl)-trans-bicyclo[3.3.0]octane

[0132]

[0133] 3-Oxo-7-(4′-methylphenyl)-trans-bicyclo[3.3.0]octane

[0134]

[0135] 3-Oxo-7-(4'-but...

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Abstract

The present invention provides one novel kind of 3, 7-disubstituted trans-dicyclo[3, 3, 0] octane compound and its preparation process and the application in liquid crystal composition. The compound has stable structure, stable property, excellent low temperature intersolubility, relatively low viscosity and short response time. It may be used in liquid crystal composition and the liquid crystal composition has low power consumption, low viscosity and short response time. It has excellent application foreground in TN, STN, HTN, TFT, FMLCD whole wavelength cholest LCD display.

Description

Technical field: [0001] The present invention relates to a novel 3,7-disubstituted trans-bicyclo[3.3.0]octane compound, its preparation method and the application of the compound in liquid crystal composition and liquid crystal display. Background technique: [0002] Liquid crystal materials are developing rapidly with the development of liquid crystal displays (LCDs), among which nematic liquid crystal materials for display are the fastest growing liquid crystal materials with the largest market share. As a liquid crystal material for display, it has also been greatly developed, and a large number of liquid crystal compounds have appeared. From biphenyl nitriles, esters, oxygen-containing heterocyclic benzenes, and pyrimidine ring liquid crystal compounds to cyclohexyl (bi) benzenes, diphenylacetylenes, ethyl bridges, olefinic end group liquid crystals and various Fluorine-containing aromatic ring liquid crystal compounds, Japan recently synthesized structurally stable dif...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/687C07C49/67C07C49/753C07C49/443C07C49/517C07C25/18C07C25/24C07C43/235C07D317/72C09K19/06G02F1/13
Inventor 康杰姜天孟田秋峰
Owner 石家庄永生华清液晶有限公司