3,7-disubstituted trans-dicyclo[3,3,0] octane compound and its prepn and use
A compound and disubstitution technology, applied in chemical instruments and methods, organic chemistry, instruments, etc., to achieve good low-temperature miscibility, moderate birefringence, and low power consumption
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Example 1
This example relates to the synthesis of intermediate 7,7-ethylenedioxy-3-trans bicyclo[3.3.0]octanone. 1) Synthesis of trans-bicyclo[3.3.0]octane 3,7-dione
Add 5.3 g of NaOH and 95 ml of anhydrous methanol to a 250 ml Erlenmeyer flask, stir until the NaOH is completely dissolved, and filter to obtain a NaOH / anhydrous methanol solution. Add 22.5 g of dimethyl acetone dicarboxylate, N 2 Under protection, add NaOH / anhydrous methanol solution with stirring, a white solid precipitates out, heat to reflux until the solid dissolves. Add 9.4 ml of 40% glyoxal aqueous solution dropwise, add in 25 minutes, and a solid precipitates out, then heat to reflux for 10 minutes, cool to room temperature, filter to obtain a yellow solid, and wash twice with 50 ml of cold methanol respectively.
Add 21 ml of 37% hydrochloric acid and 60 ml of water solution and yellow solid into a 250 ml three-necked flask, heat reflux for 3 hours, cool, and extract three times...
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Example 2
3-pentyl-7-(4′-propylphenyl)ethyl-trans bicyclo[3.3.0]octane
The reaction process is as follows:
Add 3 g of magnesium shavings and 20 ml of anhydrous tetrahydrofuran to a 250 ml three-necked flask, and add 22 g of 3,5-difluorobromobenzene (99.7%) and 40 ml of anhydrous tetrahydrofuran to a 100 ml dropping funnel. Add 5 ml of the solution dropwise to initiate the reaction. The tetrahydrofuran solution was slowly added dropwise to maintain a slight reflux. After dripping, heat to reflux for 1 hour until the magnesium chips almost disappeared. A solution of 18 g of 7,7-ethanedioxy-3-trans bicyclo[3.3.0]octanone and 40 ml of tetrahydrofuran was added dropwise, and the solution 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. Pour into water, a large amount of sediment will separate out, filter, and discard the filtrate. Put 2 grams of...
Example Embodiment
Example 3
3-pentyl-7-(4′-propylphenyl)ethyl-trans bicyclo[3.3.0]octane
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 single-mouth bottle, 600 One milliliter of 88% formic acid, 200 milliliters of toluene, stir at room temperature for 12 hours, separate the layers, wash the toluene layer until it is neutral, and anhydrous Na 2 SO 4 Dry for 4 hours, filter and evaporate the solvent to obtain 16.15 g of 3-oxo-7-(3',4'-difluorophenyl)-trans-bicyclo[3.3.0]octane, melting point 44℃, gas purity 99.7 %.
The compound (b-n) obtained in Example 3 was hydrolyzed by referring to the same method as above to obtain the following compound:
3-oxo-7-(3′,5′-difluorophenyl)-trans bicyclo[3.3.0]octane
3-pentyl-7-(4′-propylphenyl)ethyl-trans bicyclo[3.3.0]octane
3-pentyl-7-(4′-propylphenyl)ethyl-trans bicyclo[3.3.0]octane
3-pentyl-7-(4′-propylphenyl)ethyl-trans bicyclo[3.3.0]octane
3-pent...
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