CN104276934A - Chemical synthesis method of 4,8- dihydroxyl-1-tetralone - Google Patents
Chemical synthesis method of 4,8- dihydroxyl-1-tetralone Download PDFInfo
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- CN104276934A CN104276934A CN201410502166.3A CN201410502166A CN104276934A CN 104276934 A CN104276934 A CN 104276934A CN 201410502166 A CN201410502166 A CN 201410502166A CN 104276934 A CN104276934 A CN 104276934A
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
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- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/29—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of oxygen-containing functional groups
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- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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Abstract
The invention discloses a chemical synthesis method of 4,8- dihydroxyl-1-tetralone. The chemical synthesis method comprises the following steps: by taking 5-hydroxyl- tetralone as a raw material, firstly, adding NaBH4 to synthesize 5-hydroxyl-tetralol by taking methanol as a solvent, and adding benzoyl chloride to synthesize 1,5-dibenzoyl- tetrahydronaphthalene by taking pyridine as a solvent; then, adding benzene, diatomite, pyridinium dichromate and tert-butyl hydroperoxide to synthesize 4,8- dibenzoyl-1-tetralone; and finally, adding cesium carbonate to synthesize 4,8- dihydroxyl-1-tetralon by taking methanol as a solvent. The chemical synthesis method disclosed by the invention is simple in process, green and environmentally friendly and high in product purity which reaches 99.82%, and has a reaction total yield of 39-47%.
Description
Technical field
The present invention relates to 4,8-dihydroxyl-ALPHA-tetralone, be specifically related to the chemical synthesis process of 4,8-dihydroxyl-ALPHA-tetralone.
Background technology
4,8-dihydroxyl-ALPHA-tetralone (4,8-DHT), chemical name 4,8-dihydroxy-1-tetralone, colourless thin bunch of needle crystal, wherein 4 carbon be connected with hydroxyl are a chiral carbon, have the effects such as antitumor, antimycotic, hypoglycemic and immunomodulatory.The levo-enantiomer (– of 4,8-DHT) be called as regiolone, dextrorotatory antipode (+) is called as isosclerone, and 4,8-DHT also has racemic modification.Regiolone identifies the earliest from blue or green walnut, can be used for illness such as treatment skin pruritus and pain etc.Isosclerone be the earliest from
sclerotinia sclerotiummiddle isolation identification goes out, and has also isolated this compound afterwards from some fungies, and it can cause grape gray corrosion sick.Just 4,8-DHT of racemic modification is found in Semen Caryae Cathayensis.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of chemical synthesis process of 4,8-dihydroxyl-ALPHA-tetralone, and the method technique is simple, and environmental protection, product purity is high.
The present invention solves the problems of the technologies described above adopted technical scheme: the chemical synthesis process of 4,8-dihydroxyl-ALPHA-tetralone, and step is as follows:
(1) 1g 5-dihydroxy-tetrahydro naphthalenone is dissolved in 20-25ml methyl alcohol, adds 0.35-0.45g NaBH
4stirring at room temperature reaction 30min, with ammonium chloride cancellation reaction, is evaporated to dry, the ethyl acetate of volume ratio 1:1 and water mixed solvent 50-75ml is used to extract again, draw organic phase, add saturated aqueous common salt 50ml and stir, leave standstill phase-splitting, draw organic phase, add anhydrous sodium sulphate 0.5-0.7g to stir, leave standstill phase-splitting, then draw organic phase, be evaporated to dry, obtain compound as white solid: 5-dihydroxy-tetrahydro naphthalene alcohol;
(2) above-mentioned 5-dihydroxy-tetrahydro naphthalene alcohol is dissolved in 5ml pyridine, slow dropping Benzoyl chloride 1.5-2.0ml, room temperature reaction 20h, add 10-15ml distilled water diluting, 35-50 ml extracted with diethyl ether, dilute hydrochloric acid and the sodium hydrogen carbonate solution 25-50ml of extraction liquid volume ratio 1:1 stir, leave standstill phase-splitting, draw organic phase, stir with saturated aqueous common salt 50ml again, leave standstill phase-splitting, draw organic phase, be evaporated to dry, mix with weight ratio 1:1 and 300-400 order silica gel, cross 200-300 order silicagel column, ethyl acetate with volume ratio 1:6-8: sherwood oil mixed solution wash-out, elutriant is evaporated to dry, obtain faint yellow solid compound: 1, 5-dibenzoyl-naphthane,
(3) by above-mentioned 1,5-dibenzoyl-naphthane is dissolved in 9.5-10ml benzene, 0.47-0.55g diatomite, 0.81-1.0g pyridinium dichromate and 1.5-1.8ml tertbutyl peroxide is added respectively at 0 DEG C, again at stirring at room temperature reaction 24h, suction filtration after the dilution of 15-40ml ether, be evaporated to dry, mix with weight ratio 1:1 and 300-400 order silica gel, cross 200-300 order silicagel column, ethyl acetate with volume ratio 1:4-5: sherwood oil mixed solution wash-out, elutriant is evaporated to dry, obtains yellow solid compound: 4,8-dibenzoyl-ALPHA-tetralone;
(4) by above-mentioned 4, 8-dibenzoyl-ALPHA-tetralone is dissolved in 8-10ml methyl alcohol, add 0.14-0.18g cesium carbonate, room temperature reaction 4h, removing methyl alcohol, extraction into ethyl acetate three times, each ethyl acetate 25ml, combining extraction liquid, add saturated aqueous common salt 50-80ml to stir, leave standstill phase-splitting, draw organic phase, be evaporated to drying, mix with weight ratio 1:1 and 300-400 order silica gel, cross 200-300 order silicagel column, ethyl acetate with volume ratio 1:1: sherwood oil mixed solution wash-out, elutriant is evaporated to dry, add ethyl acetate crystallization, obtain 4, the colourless bulk crystalline of 8-dihydroxyl-ALPHA-tetralone.
Compared with prior art, the invention has the advantages that the chemical synthesis process of 4,8-dihydroxyl-ALPHA-tetralone, with 5-dihydroxy-tetrahydro naphthalenone for raw material, first is that solvent adds NaBH with methyl alcohol
4synthesize 5-dihydroxy-tetrahydro naphthalene alcohol; be that solvent adds Benzoyl chloride and synthesizes 1 again with pyridine; 5-dibenzoyl-naphthane; then add benzene, diatomite, pyridinium dichromate and tertbutyl peroxide and synthesize 4; 8-dibenzoyl-ALPHA-tetralone; last methyl alcohol is solvent, adds cesium carbonate synthesis and obtains 4,8-dihydroxyl-ALPHA-tetralone.Method technique is simple, and environmental protection, product purity is high, reaches 99.82%, and overall yield of reaction is 39-47%.
Accompanying drawing explanation
Fig. 1 is 4,8-dihydroxyl-ALPHA-tetralone structure iron;
Fig. 2 is 5-dihydroxy-tetrahydro naphthalenone structure iron;
Fig. 3 is 5-dihydroxy-tetrahydro naphthalene alcohol structure iron;
Fig. 4 is 1,5-dibenzoyl-naphthane structure iron;
Fig. 5 is 4,8-dibenzoyl-ALPHA-tetralone structure iron.
Embodiment
Below in conjunction with accompanying drawing embodiment, the present invention is described in further detail.
Embodiment 1
First 1g 5-dihydroxy-tetrahydro naphthalenone is dissolved in 20ml methyl alcohol, adds 0. 35gNaBH
4stirring at room temperature reaction 30min, ammonium chloride cancellation is reacted, be evaporated to dry, ethyl acetate and the water mixed solvent 50ml of volume ratio 1:1 extract, 50ml saturated common salt is washed, after organic addition 0. 5g anhydrous sodium sulphate dewaters, be evaporated to dry, obtain compound as white solid 5-dihydroxy-tetrahydro naphthalene alcohol, be dissolved in 5ml pyridine, slow dropping 1.5ml Benzoyl chloride, room temperature reaction 20h, add 10ml distilled water diluting, 35ml extracted with diethyl ether, extraction liquid adds the dilute hydrochloric acid of volume ratio 1:1 and sodium hydrogen carbonate solution 25ml stirs, leave standstill phase-splitting, draw organic phase, stir with saturated aqueous common salt 50ml again, leave standstill phase-splitting, draw organic phase, be evaporated to dry, mix with weight ratio 1:1 and 300 order silica gel, cross 200-300 order silicagel column, ethyl acetate with volume ratio 1:6: sherwood oil mixed solution wash-out, elutriant is evaporated to dry, obtain faint yellow solid compound: 1, 5-dibenzoyl-naphthane, be dissolved in 9.5-10ml benzene, 0.47g diatomite, 0.81g pyridinium dichromate and 1.5ml tertbutyl peroxide is added respectively at 0 DEG C, suction filtration after the dilution of stirring at room temperature reaction 24h, 15ml ether, is evaporated to dry again, mix with weight ratio 1:1 and 300 order silica gel, cross 200-300 order silicagel column, the ethyl acetate with volume ratio 1:4-5: sherwood oil mixed solution wash-out, elutriant is evaporated to dry, obtain yellow solid compound: 4,8-dibenzoyl-ALPHA-tetralone, be dissolved in 8ml methyl alcohol, add 0.14g cesium carbonate, room temperature reaction 4h, removing methyl alcohol, extraction into ethyl acetate three times, each ethyl acetate 25ml, combining extraction liquid, add saturated aqueous common salt 50ml to stir, leave standstill phase-splitting, draw organic phase, be evaporated to drying, mix with weight ratio 1:1 and 300 order silica gel, cross 200-300 order silicagel column, the ethyl acetate with volume ratio 1:1: sherwood oil mixed solution wash-out, elutriant is evaporated to dry, add ethyl acetate crystallization, obtain the colourless bulk crystalline of 4,8-dihydroxyl-ALPHA-tetralone.Above-mentioned overall yield of reaction is about 39%, adopts high effective liquid chromatography for measuring, obtains purity and reach 99.82%.4,8-DHT fusing point 366-368K, water-soluble, ethanol, acetone and chloroform, [α]
20 d=± 0 ° of (c1.3, CH
2cl
2), be racemic modification.
Embodiment 2
First just 1g 5-dihydroxy-tetrahydro naphthalenone is dissolved in 25ml methyl alcohol, adds 0.45g NaBH
4stirring at room temperature reaction 30min, with ammonium chloride cancellation reaction, is evaporated to dry, the ethyl acetate of volume ratio 1:1 and water mixed solvent 75ml is used to extract again, draw organic phase, add saturated aqueous common salt 50ml and stir, leave standstill phase-splitting, draw organic phase, add anhydrous sodium sulphate 0.7g to stir, leave standstill phase-splitting, then draw organic phase, be evaporated to dry, obtain compound as white solid: 5-dihydroxy-tetrahydro naphthalene alcohol, be dissolved in 5ml pyridine, slow dropping Benzoyl chloride 2.0ml, room temperature reaction 20h, add 15ml distilled water diluting, 50ml extracted with diethyl ether, extraction liquid adds the dilute hydrochloric acid of volume ratio 1:1 and sodium hydrogen carbonate solution 50ml stirs, leave standstill phase-splitting, draw organic phase, stir with saturated aqueous common salt 50ml again, leave standstill phase-splitting, draw organic phase, be evaporated to dry, mix with weight ratio 1:1 and 400 order silica gel, cross 200-300 order silicagel column, ethyl acetate with volume ratio 1:8: sherwood oil mixed solution wash-out, elutriant is evaporated to dry, obtain faint yellow solid compound: 1, 5-dibenzoyl-naphthane, be dissolved in 9.5-10ml benzene, 0.55g diatomite, 1.0g pyridinium dichromate and 1.8ml tertbutyl peroxide is added respectively at 0 DEG C, suction filtration after the dilution of stirring at room temperature reaction 24h, 40ml ether, is evaporated to dry again, mix with weight ratio 1:1 and 400 order silica gel, cross 200-300 order silicagel column, the ethyl acetate with volume ratio 1:4-5: sherwood oil mixed solution wash-out, elutriant is evaporated to dry, obtain yellow solid compound: 4,8-dibenzoyl-ALPHA-tetralone, be dissolved in 10ml methyl alcohol, add 0.18g cesium carbonate, room temperature reaction 4h, removing methyl alcohol, extraction into ethyl acetate three times, each ethyl acetate 25ml, combining extraction liquid, add saturated aqueous common salt 80ml to stir, leave standstill phase-splitting, draw organic phase, be evaporated to drying, mix with weight ratio 1:1 and 400 order silica gel, cross 200-300 order silicagel column, the ethyl acetate with volume ratio 1:1: sherwood oil mixed solution wash-out, elutriant is evaporated to dry, add ethyl acetate crystallization, obtain the colourless bulk crystalline of 4,8-dihydroxyl-ALPHA-tetralone, overall yield of reaction is 41%, adopts high effective liquid chromatography for measuring, obtains purity and reach 99.82%.
Embodiment 3
First just 1g 5-dihydroxy-tetrahydro naphthalenone is dissolved in 23ml methyl alcohol, adds 0.40g NaBH
4stirring at room temperature reaction 30min, with ammonium chloride cancellation reaction, is evaporated to dry, the ethyl acetate of volume ratio 1:1 and water mixed solvent 60ml is used to extract again, draw organic phase, add saturated aqueous common salt 50ml and stir, leave standstill phase-splitting, draw organic phase, add anhydrous sodium sulphate 0.6g to stir, leave standstill phase-splitting, then draw organic phase, be evaporated to dry, obtain compound as white solid: 5-dihydroxy-tetrahydro naphthalene alcohol, be dissolved in 5ml pyridine, slow dropping Benzoyl chloride 1.8ml, room temperature reaction 20h, add 12 ml distilled water dilutings, 42 ml extracted with diethyl ether, extraction liquid adds the dilute hydrochloric acid of volume ratio 1:1 and sodium hydrogen carbonate solution 40ml stirs, leave standstill phase-splitting, draw organic phase, stir with saturated aqueous common salt 50ml again, leave standstill phase-splitting, draw organic phase, be evaporated to dry, mix with weight ratio 1:1 and 350 order silica gel, cross 200-300 order silicagel column, ethyl acetate with volume ratio 1:7: sherwood oil mixed solution wash-out, elutriant is evaporated to dry, obtain faint yellow solid compound: 1, 5-dibenzoyl-naphthane, be dissolved in 9.5-10ml benzene, 0.50g diatomite, 0.9g pyridinium dichromate and 1.6ml tertbutyl peroxide is added respectively at 0 DEG C, suction filtration after the dilution of stirring at room temperature reaction 24h, 25ml ether, is evaporated to dry again, mix with weight ratio 1:1 and 350 order silica gel, cross 200-300 order silicagel column, the ethyl acetate with volume ratio 1:4-5: sherwood oil mixed solution wash-out, elutriant is evaporated to dry, obtain yellow solid compound: 4,8-dibenzoyl-ALPHA-tetralone, be dissolved in 9ml methyl alcohol, add 0.16g cesium carbonate, room temperature reaction 4h, removing methyl alcohol, extraction into ethyl acetate three times, each ethyl acetate 25ml, combining extraction liquid, add saturated aqueous common salt 65ml to stir, leave standstill phase-splitting, draw organic phase, be evaporated to drying, mix with weight ratio 1:1 and 350 order silica gel, cross 200-300 order silicagel column, the ethyl acetate with volume ratio 1:1: sherwood oil mixed solution wash-out, elutriant is evaporated to dry, add ethyl acetate crystallization, obtain the colourless bulk crystalline of 4,8-dihydroxyl-ALPHA-tetralone, overall yield of reaction is 47%, adopts high effective liquid chromatography for measuring, obtains purity and reach 99.82%.
Claims (1)
- The chemical synthesis process of 1.4,8-dihydroxyl-ALPHA-tetralone, step is as follows:(1) 1g 5-dihydroxy-tetrahydro naphthalenone is dissolved in 20-25ml methyl alcohol, adds 0.35-0.45g NaBH 4stirring at room temperature reaction 30min, with ammonium chloride cancellation reaction, is evaporated to dry, the ethyl acetate of volume ratio 1:1 and water mixed solvent 50-75ml is used to extract again, draw organic phase, add saturated aqueous common salt 50ml and stir, leave standstill phase-splitting, draw organic phase, add anhydrous sodium sulphate 0.5-0.7g to stir, leave standstill phase-splitting, draw organic phase, be evaporated to dry, obtain compound as white solid: 5-dihydroxy-tetrahydro naphthalene alcohol;(2) above-mentioned 5-dihydroxy-tetrahydro naphthalene alcohol is dissolved in 5ml pyridine, slow dropping Benzoyl chloride 1.5-2.0ml, room temperature reaction 20h, add 10-15ml distilled water diluting, use 35-50ml extracted with diethyl ether, extraction liquid adds volume ratio 1:1 dilute hydrochloric acid and sodium hydrogen carbonate solution 25-50ml stirs, leave standstill phase-splitting, draw organic phase, stir with saturated aqueous common salt 50ml, leave standstill phase-splitting, draw organic phase, be evaporated to dry, mix with weight ratio 1:1 and 300-400 order silica gel, cross 200-300 order silicagel column, ethyl acetate with volume ratio 1:6-8: sherwood oil mixed solution wash-out, elutriant is evaporated to dry, obtain faint yellow solid compound: 1, 5-dibenzoyl-naphthane,(3) by above-mentioned 1, 5-dibenzoyl-naphthane is dissolved in 9.5-10ml benzene, 0.47-0.55g diatomite is added respectively at 0 DEG C, 0.81-1.0g pyridinium dichromate and 1.5-1.8ml tertbutyl peroxide, again at stirring at room temperature reaction 24h, with suction filtration after the dilution of 15-40ml ether, be evaporated to dry, mix with weight ratio 1:1 and 300-400 order silica gel, cross 200-300 order silicagel column, ethyl acetate with volume ratio 1:4-5: sherwood oil mixed solution wash-out, elutriant is evaporated to dry, obtain yellow solid compound: 4, 8-dibenzoyl-ALPHA-tetralone,(4) by above-mentioned 4, 8-dibenzoyl-ALPHA-tetralone is dissolved in 8-10ml methyl alcohol, add 0.14-0.18g cesium carbonate room temperature reaction 4h, removing methyl alcohol, extraction into ethyl acetate three times, each ethyl acetate 25ml, combining extraction liquid, add saturated aqueous common salt 50-80ml to stir, leave standstill phase-splitting, draw organic phase, be evaporated to drying, mix with weight ratio 1:1 and 300-400 order silica gel, cross 200-300 order silicagel column, ethyl acetate with 1:1: sherwood oil mixed solution wash-out, elutriant is evaporated to dry, add ethyl acetate crystallization, obtain 4, the colourless bulk crystalline of 8-dihydroxyl-ALPHA-tetralone.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1274723A (en) * | 1993-07-22 | 2000-11-29 | 伊莱利利公司 | Dicyclic compound, medicine composition containing the same and use thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1274723A (en) * | 1993-07-22 | 2000-11-29 | 伊莱利利公司 | Dicyclic compound, medicine composition containing the same and use thereof |
Non-Patent Citations (2)
| Title |
|---|
| R.H.THOMSON: "The reduction of Juglone", 《JOURNAL OF THE CHEMICAL SOCIETY》 * |
| XIN WANG,ET AL: "Synthesis of Cinacalcet congeners", 《TETRAHEDRON LETTERS》 * |
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