CN102532087A - Method for synthesizing 3-methyl-7,8-dimethoxy-chroman-4-one - Google Patents
Method for synthesizing 3-methyl-7,8-dimethoxy-chroman-4-one Download PDFInfo
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Abstract
The method relates to the fields of organic chemistry and pharmaceutical chemistry, in particular to a method for synthesizing 3-methyl-7,8-dimethoxy-chroman-4-one. The 3-methyl-7,8-dimethoxy-chroman-4-one is efficiently synthesized by taking trifluoroacetic anhydride as a catalyst. Compared with the conventional preparation method, the method has the advantages that: the yield is higher, conditions are simpler, a reagent is more readily available, posttreatment is simple, industrial production is more convenient to implement, and the like.
Description
Technical field
The present invention relates to a kind of 3-methyl-7; The preparation method of 8-dimethoxy isochromanome-4; 3-methyl-7,8-dimethoxy isochromanome-the 4th, the midbody of synthetic Pericarpium Musae antihypertensive active composition the invention belongs to organic chemistry compound method and pharmaceutical chemistry field.
Background technology
Hypertension is the common cardiovascular disorder of popular in the world wide, is apoplexy, heart failure, and the primary hazard factor of renal failure, simultaneously in close relations with coronary heart disease and mellitus, become and caused human cardiovascular disease's main causes of death at present.Antihypertensive drug research is the key areas of new drug research; From medicinal plant, separate and have hypotensive activity reactive site and activeconstituents; And be that the guide carries out complete synthesis and composition optimizes is modified with the active compound, the research of antihypertensive drug is had great importance.The antihypertensive drug that has gone on the market at present has hundreds of; 1999, WHO/ISH hypertension practice guidelines recommended to use diuretic(s), beta-blocker, calcium antagonist, angiotensin-convertion enzyme inhibitor, ARB, six big types of antihypertensive drug of alpha-blocking agent.21 century is the century of green Sustainable development, and back to nature has been a present megatrend.The application of natural drug more and more comes into one's own, and the natural product of seeking biologically active is the field that new drug research merits attention.It has been found that a lot of natural products with antihypertensive activity in recent years, some of them successfully are developed as new drug and are applied to clinical.
Pericarpium Musae has effects such as heat-clearing, moistening lung, laxation, detoxifcation, the treatment that is mainly used in symptoms such as hypertension, arteriosclerosis, constipation, dysentery, tonsillitis among the people.Record Pericarpium Musae or carpopodium 30～60g in " modern Chinese herbal medicine voluminous dictionary " fry in shallow oil the soup clothes, can be used for hypertension therapeutic.The clinical use of the fragrant shepherd's purse step-down particle of Chinese patent medicine for many years, hypotensive effect is obvious.The monarch drug in a prescription of this medicine promptly is a Pericarpium Musae, and shepherd's purse is its ministerial drug.The research of the activeconstituents of Pericarpium Musae being carried out extraction separation has been carried out in the previous work of this seminar; In conjunction with pharmacological evaluation, the active tracking, confirm Pericarpium Musae antihypertensive activity position, further the separation and purification reactive site; Obtain a brand-new compound 3-methyl-7; 8-dihydroxyl isochromanome-4 (XJP), pharmacology activity research finds that its antihypertensive active is remarkable
1,2(1, patent CN 1857530A; 2, number of patent application: 200710019203.5).
In the study on the synthesis of this seminar to XJP; Adopted two kinds of methods: a kind of is with 2; 3-3,5-dimethoxybenzoic alcohol and 2 halogenated ethyl propionate generation etherification reactions, perhaps with 2,3-dimethoxy benzyl bromine or 2; 3-dimethoxy benzyl chlorine and ethyl lactate generation etherification reaction obtain 2-(2,3-dimethoxy benzyloxy) ethyl propionate.Again 2-(2,3-dimethoxy benzyloxy) ethyl propionate hydrolysis is obtained 2-(2,3-dimethoxy benzyloxy) propionic acid; Then 2-(2,3-dimethoxy benzyloxy) propionic acid is prepared into 2-(2,3-dimethoxy benzyloxy) propionyl chloride; Issue living intramolecularly in the Louis acid catalysis condition and pay the gram acylation reaction, obtain 3-methyl-7,8-dimethoxy isochromanome-4; Remove methyl at last and obtain target compound 3-methyl-7,8-dihydroxyl isochromanome-4
3(number of patent application: 200710020464.9); Another kind is with 2; 3-3,5-dimethoxybenzoic alcohol and N-bromosuccinimide (NBS) reaction obtains 2,3-dimethoxy-6-bromobenzene methyl alcohol, 2; 3-dimethoxy-6-bromobenzene methyl alcohol and 2 bromopropionic acid ethyl ester generation etherification reaction obtain 2-(2,3-dimethoxy-6-bromo-benzyloxy-) ethyl propionate.Again with 2-(2; 3-dimethoxy-6-bromo-benzyloxy-) the ethyl propionate hydrolysis obtains 2-(2,3-dimethoxy-6-bromo-benzyloxy-) propionic acid, then under nitrogen protection; Carry out cyclization with n-Butyl Lithium catalysis and obtain 3-methyl-7; 8-dimethoxy isochromanome-4 removes methyl at last and obtains target compound 3-methyl-7,8-dihydroxyl isochromanome-4
4(Bioorganic & Medicinal Chemistry Letters 19 (2009) 1822-1824).But all there is defective in these two kinds of methods, are carrying out compound 3-methyl-7, and the first method productive rate is extremely low during 8-dimethoxy isochromanome-4 synthetic, and the second method operational condition is relatively harsher, and certain danger is arranged, and all is not suitable for mass production.
The present invention with trifluoro-acetic anhydride as catalyzer, directly with 2-(2,3-dimethoxy benzyloxy) propionic acid as substrate, adopt the synthetic 3-methyl-7,8-dimethoxy isochromanome-4 of obtaining of Fu Ke acylation reaction; Compound method of the present invention has the yield height, and condition is simple, and conversion unit is simple, is easy to plurality of advantages such as suitability for industrialized production.
Summary of the invention
The purpose of this invention is to provide a kind of synthetic above-mentioned 3-methyl-7, the method for 8-dimethoxy isochromanome-4;
The objective of the invention is to realize through following technical scheme:
3-methyl-7; The preparation method of 8-dimethoxy isochromanome-4 (reaction 1); May further comprise the steps: under trifluoro-acetic anhydride catalysis, be that raw material carries out the Fu Ke acylation reaction in organic solvent with 2-(2,3-dimethoxy benzyloxy) propionic acid; Catalyzer of the present invention comprises polyphosphoric acid, methanesulfonic, trifluoracetic acid, trifluoro-acetic anhydride, is preferably trifluoro-acetic anhydride; Described organic solvent is selected from methylene dichloride, ETHYLE ACETATE, and acetone, acetonitrile, toluene, benzene, normal hexane, methyl alcohol, N, dinethylformamide or DMSO 99.8MIN. are preferably used toluene; Described temperature is 25-80 ℃, preferably uses 60 ℃; The described time is 1-4 hour, preferably uses 2 hours; The consumption of described trifluoro-acetic anhydride is a 1-10 times of equivalent, preferably uses 2 times of equivalents.
Reaction 1
With reference to reacting 1 diagram:
Under trifluoro-acetic anhydride catalysis, be raw material with 2-(2,3-dimethoxy benzyloxy) propionic acid, toluene is solvent, 60 ℃ of reactions obtain 3-methyl-7,8-dimethoxy isochromanome-4.
Embodiment
Further describe the present invention below in conjunction with specific embodiment, advantage of the present invention and characteristics will be more clear along with description.But these embodiment only are exemplary, scope of the present invention are not constituted any restriction.It will be understood by those skilled in the art that and down can make amendment with form or replace without departing from the spirit and scope of the present invention, but these modifications and replacing all fall in protection scope of the present invention the details of technical scheme of the present invention.
Embodiment 1
3-methyl-7, the preparation (1) of 8-dimethoxy isochromanome-4
Get a reaction flask, add 670 milligrams of polyphosphoric acid (PPA), be heated to 60 ℃ it can be stirred, slowly add 240 milligrams of 2-(2,3-dimethoxy benzyloxy) propionic acid, be heated to 110 ℃ of reactions 8 hours.With 20 ml water dilute reaction solutions, use ethyl acetate extraction then three times, merge organic phase, water, potassium hydroxide solution and saturated common salt water washing respectively, anhydrous sodium sulfate drying.Decompression with the solvent evaporate to dryness after through silicagel column (sherwood oil: ETHYLE ACETATE=10: 1) separate and to obtain micro-product.
Embodiment 2
3-methyl-7, the preparation (2) of 8-dimethoxy isochromanome-4
Get a reaction flask; With 240 milligrams of 2-(2; 3-dimethoxy benzyloxy) propionic acid is dissolved in 20 milliliters of chloroforms, adds successively under 300 milligrams of cyanuryl chlorides, 160 milligrams of aluminum chlorides and 0.1 milliliter of anhydrous pyridine room temperature to react four hours, and it is too many and micro-to obtain assorted point.
Embodiment 3
3-methyl-7, the preparation (3) of 8-dimethoxy isochromanome-4
Get a reaction flask, add 1.2 gram 2-(2,3-dimethoxy benzyloxy) propionic acid, under condition of ice bath, drip SOCl
22ml dropwised room temperature reaction 2 hours, removed excessive SOCl under reduced pressure
2, add benzene 5ml dissolving.The benzole soln of 2-(2,3-dimethoxy benzyloxy) propionyl chloride is splashed into ice bath refrigerative ZnCl
2In the suspension-s of 700 milligrams benzene, reacted 4～5 hours, in the Hydrogen chloride with reaction solution impouring 2mol/L; Tell organic layer, the sour water layer is with extracted with diethyl ether 2 times, each 40ml; Merge organic layer, use saturated sodium bicarbonate, saturated common salt water washing successively, anhydrous sodium sulfate drying.Organic layer concentrates, silica gel column chromatography (sherwood oil: ETHYLE ACETATE=10: 1) separate 41.2 milligrams of white solids, yield 5.3%.
Embodiment 4
3-methyl-7, the preparation (4) of 8-dimethoxy isochromanome-4
Get a reaction flask, add 120 milligrams of 2-(2,3-dimethoxy benzyloxy) propionic acid and 0.5 milliliter of trifluoro-acetic anhydride; Ice bath reacted 6 hours down; With 100 milliliters of ETHYLE ACETATE dilute reaction solutions, use sodium hydrogen carbonate solution, water and saturated common salt water washing respectively, anhydrous sodium sulfate drying.Decompression with the solvent evaporate to dryness after through silicagel column (sherwood oil: ETHYLE ACETATE=10: 1) separate and to obtain 25 milligrams of white solids, productive rate 22.3%.
Embodiment 5
3-methyl-7, the preparation (5) of 8-dimethoxy isochromanome-4
Get a reaction flask, add 120 milligrams of 2-(2,3-dimethoxy benzyloxy) propionic acid and 0.5 milliliter of trifluoro-acetic anhydride; Reaction is 4 hours under the room temperature; With 100 milliliters of ETHYLE ACETATE dilute reaction solutions, use sodium hydrogen carbonate solution, water and saturated common salt water washing respectively, anhydrous sodium sulfate drying.Decompression separates through silicagel column after with the solvent evaporate to dryness and obtains 30 milligrams of white solids, productive rate 26.8%.
Embodiment 6
3-methyl-7, the preparation (6) of 8-dimethoxy isochromanome-4
Get a reaction flask, add 120 milligrams of 2-(2,3-dimethoxy benzyloxy) propionic acid and 0.5 milliliter of trifluoro-acetic anhydride; 40 ℃ were reacted 4 hours down; With 100 milliliters of ETHYLE ACETATE dilute reaction solutions, use sodium hydrogen carbonate solution, water and saturated common salt water washing respectively, anhydrous sodium sulfate drying.Decompression separates (sherwood oil: ETHYLE ACETATE=10: 1) obtain 20 milligrams of white solids, productive rate 17.8% through silicagel column after with the solvent evaporate to dryness.
Embodiment 7
3-methyl-7, the preparation (7) of 8-dimethoxy isochromanome-4
Get a reaction flask; Add 120 milligrams of 2-(2; 3-dimethoxy benzyloxy) propionic acid, 0.25 milliliter of trifluoracetic acid and 0.5 milliliter of trifluoro-acetic anhydride, reaction is 2 hours under the room temperature, with 100 milliliters of ETHYLE ACETATE dilute reaction solutions; Use sodium hydrogen carbonate solution, water and saturated common salt water washing respectively, anhydrous sodium sulfate drying.Decompression with the solvent evaporate to dryness after through silicagel column (sherwood oil: ETHYLE ACETATE=10: 1) separate and to obtain 32 milligrams of white solids, productive rate 28.6%.
Embodiment 8
3-methyl-7, the preparation (8) of 8-dimethoxy isochromanome-4
Get a reaction flask, add 120 milligrams of 2-(2,3-dimethoxy benzyloxy) propionic acid and 0.5 milliliter of trifluoro-acetic anhydride; Reaction is 2 hours under the room temperature; With 100 milliliters of ETHYLE ACETATE dilute reaction solutions, use sodium hydrogen carbonate solution, water and saturated common salt water washing respectively, anhydrous sodium sulfate drying.Decompression separates (sherwood oil: ETHYLE ACETATE=10: 1) obtain 25 milligrams of white solids, productive rate 22.3% through silicagel column after with the solvent evaporate to dryness.
Embodiment 9
3-methyl-7, the preparation (9) of 8-dimethoxy isochromanome-4
Get a reaction flask; Add 120 milligrams of 2-(2; 3-dimethoxy benzyloxy) propionic acid, 0.25 milliliter of trifluoracetic acid and 0.5 milliliter of trifluoro-acetic anhydride, reaction is 4 hours under the room temperature, with 100 milliliters of ETHYLE ACETATE dilute reaction solutions; Use sodium hydrogen carbonate solution, water and saturated common salt water washing respectively, anhydrous sodium sulfate drying.Decompression with the solvent evaporate to dryness after through silicagel column (sherwood oil: ETHYLE ACETATE=10: 1) separate and to obtain 18 milligrams of white solids, productive rate 16.1%.
Embodiment 10
3-methyl-7, the preparation (10) of 8-dimethoxy isochromanome-4
Get a reaction flask; Add 120 milligrams of 2-(2; 3-dimethoxy benzyloxy) propionic acid, 0.25 milliliter of trifluoracetic acid and 0.5 milliliter of trifluoro-acetic anhydride, reaction is 6 hours under the room temperature, with 100 milliliters of ETHYLE ACETATE dilute reaction solutions; Use sodium hydrogen carbonate solution, water and saturated common salt water washing respectively, anhydrous sodium sulfate drying.Decompression separates through silicagel column after with the solvent evaporate to dryness and obtains 30 milligrams of white solids, productive rate 26.7%.
Embodiment 11
3-methyl-7, the preparation (11) of 8-dimethoxy isochromanome-4
Get a reaction flask; Add 120 milligrams of 2-(2; 3-dimethoxy benzyloxy) propionic acid, 0.1 milliliter of trifluoracetic acid and 0.5 milliliter of trifluoro-acetic anhydride, reaction is 6 hours under the room temperature, with 100 milliliters of ETHYLE ACETATE dilute reaction solutions; Use sodium hydrogen carbonate solution, water and saturated common salt water washing respectively, anhydrous sodium sulfate drying.Decompression with the solvent evaporate to dryness after through silicagel column (sherwood oil: ETHYLE ACETATE=10: 1) separate and to obtain 30 milligrams of white solids, productive rate 26.7%.
Embodiment 12
3-methyl-7, the preparation (12) of 8-dimethoxy isochromanome-4
Get a reaction flask; Add 120 milligrams of 2-(2; 3-dimethoxy benzyloxy) propionic acid, 0.1 milliliter of trifluoracetic acid and 0.1 milliliter of trifluoro-acetic anhydride, reaction is 6 hours under the room temperature, with 100 milliliters of ETHYLE ACETATE dilute reaction solutions; Use sodium hydrogen carbonate solution, water and saturated common salt water washing respectively, anhydrous sodium sulfate drying.Decompression with the solvent evaporate to dryness after through silicagel column (sherwood oil: ETHYLE ACETATE=10: 1) separate and to obtain 20 milligrams of white solids, productive rate 17.8%.
Embodiment 13
3-methyl-7, the preparation (13) of 8-dimethoxy isochromanome-4
Get a reaction flask, add 120 milligrams of 2-(2,3-dimethoxy benzyloxy) propionic acid, 0.8 milliliter of trifluoro-acetic anhydride and 5 milliliters of toluene, reaction is 4 hours under the room temperature, the product trace.
Embodiment 14
3-methyl-7, the preparation (14) of 8-dimethoxy isochromanome-4
Get a reaction flask; Add 120 milligrams of 2-(2; 3-dimethoxy benzyloxy) propionic acid, 0.8 milliliter of trifluoro-acetic anhydride and 5 milliliters of toluene, 40 ℃ were reacted 2 hours down, with 100 milliliters of ETHYLE ACETATE dilute reaction solutions; Use sodium hydrogen carbonate solution, water and saturated common salt water washing respectively, anhydrous sodium sulfate drying.Decompression with the solvent evaporate to dryness after through silicagel column (sherwood oil: ETHYLE ACETATE=10: 1) separate and to obtain 44 milligrams of white solids, productive rate 39.3%.
Embodiment 15
3-methyl-7, the preparation (15) of 8-dimethoxy isochromanome-4
Get a reaction flask; Add 120 milligrams of 2-(2; 3-dimethoxy benzyloxy) propionic acid, 0.8 milliliter of trifluoro-acetic anhydride and 5 milliliters of toluene, 60 ℃ were reacted 2 hours down, with 100 milliliters of ETHYLE ACETATE dilute reaction solutions; Use sodium hydrogen carbonate solution, water and saturated common salt water washing respectively, anhydrous sodium sulfate drying.Decompression with the solvent evaporate to dryness after through silicagel column (sherwood oil: ETHYLE ACETATE=10: 1) separate and to obtain 47 milligrams of white solids, productive rate 42.0%.
Embodiment 16
3-methyl-7, the preparation (16) of 8-dimethoxy isochromanome-4
Get a reaction flask; Add 480 milligrams of 2-(2; 3-dimethoxy benzyloxy) propionic acid, 0.8 milliliter of trifluoro-acetic anhydride and 5 milliliters of toluene, reaction is 5 hours under the room temperature, with 100 milliliters of ETHYLE ACETATE dilute reaction solutions; Use sodium hydrogen carbonate solution, water and saturated common salt water washing respectively, anhydrous sodium sulfate drying.Decompression with the solvent evaporate to dryness after through silicagel column (sherwood oil: ETHYLE ACETATE=10: 1) separate and to obtain 172 milligrams of white solids, productive rate 38.4%.
Embodiment 17
3-methyl-7, the preparation (17) of 8-dimethoxy isochromanome-4
Get a reaction flask; Add 480 milligrams of 2-(2; 3-dimethoxy benzyloxy) propionic acid, 0.8 milliliter of trifluoro-acetic anhydride and 5 milliliters of toluene, 40 ℃ were reacted 2.5 hours down, with 100 milliliters of ETHYLE ACETATE dilute reaction solutions; Use sodium hydrogen carbonate solution, water and saturated common salt water washing respectively, anhydrous sodium sulfate drying.Decompression with the solvent evaporate to dryness after through silicagel column (sherwood oil: ETHYLE ACETATE=10: 1) separate and to obtain 192 milligrams of white solids, productive rate 42.8%.
Embodiment 18
3-methyl-7, the preparation (18) of 8-dimethoxy isochromanome-4
Get a reaction flask; Add 480 milligrams of 2-(2; 3-dimethoxy benzyloxy) propionic acid, 0.8 milliliter of trifluoro-acetic anhydride and 5 milliliters of toluene, 60 ℃ were reacted 2 hours down, with 100 milliliters of ETHYLE ACETATE dilute reaction solutions; Use sodium hydrogen carbonate solution, water and saturated common salt water washing respectively, anhydrous sodium sulfate drying.Decompression separates that (sherwood oil: ETHYLE ACETATE=10: 1) wash-out obtains 299 milligrams of white solids, productive rate 67% after with the solvent evaporate to dryness through silicagel column.
Embodiment 19
3-methyl-7, the preparation (19) of 8-dimethoxy isochromanome-4
Get a reaction flask, add 12 gram 2-(2,3-dimethoxy benzyloxy) propionic acid, 20 milliliters of trifluoro-acetic anhydrides and 50 milliliters of toluene; 60 ℃ were reacted 2 hours down; With 200 milliliters of ETHYLE ACETATE dilute reaction solutions, use sodium hydrogen carbonate solution, water and saturated common salt water washing respectively, anhydrous sodium sulfate drying.Decompression separates (sherwood oil: ETHYLE ACETATE=10: 1) obtain 7.2 gram white solids, productive rate 64% through silicagel column after with the solvent evaporate to dryness.
1H-NMR(CDCl
3，300MHz)δ(ppm)1.50(d，3H，J＝6.6Hz，-CH
3)，3.85(s，3H，-OCH
3)，3.95(s，3H，-OCH
3)，4.19(q，1H，J＝6.6Hz，-CH-)，4.79(d，1H，J＝15.9Hz，-CH
2-)，5.13(d，1H，J＝15.9Hz，-CH
2-)，6.95(d，1H，J＝8.7Hz，Ar-H)，7.83(d，1H，J＝8.7Hz，Ar-H)；MS(ESI)m/z[M+H]
+223.0，[M+Na]
+245.0；IR(KBr)：2991，2979，2963，2937，2844，2826，1693，1597，1494，1454，1288，1272，1126，1079cm
-1。
Claims (7)
1. a kind of 3-methyl-7 of claim, the preparation method of 8-dimethoxy isochromanome-4 may further comprise the steps: under trifluoro-acetic anhydride catalysis, be that raw material carries out the Fu Ke acylation reaction and promptly gets in organic solvent with 2-(2,3-dimethoxy benzyloxy) propionic acid.
2. the described method of claim 1 is characterized in that described catalyzer comprises methanesulfonic, trifluoracetic acid, trifluoro-acetic anhydride, is preferably trifluoro-acetic anhydride.
3. the described method of claim 1 is characterized in that described organic solvent is selected from methylene dichloride, ETHYLE ACETATE, acetone, acetonitrile, toluene, benzene, normal hexane, methyl alcohol, N, dinethylformamide or DMSO 99.8MIN..
4. the described organic solvent of claim 3 is preferably used toluene.
5. the described method of claim 1 is characterized in that described temperature is 25-60 ℃, preferred 60 ℃.
6. the described method of claim 1 is characterized in that the described time is 1-4 hour, preferred 2 hours.
7. the described method of claim 1, the consumption that it is characterized in that described trifluoro-acetic anhydride is a 1-10 times of equivalent, preferred 2 times of equivalents.
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| CN103570665A (en) * | 2012-07-23 | 2014-02-12 | 中国药科大学 | Enantiomers of 3-methyl-7, 8-dihydroxy-isochroman-4-one, and applications thereof in controlling cardiovascular diseases |
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| CN101016290A (en) * | 2007-03-01 | 2007-08-15 | 中国药科大学 | Method of synthesizing 3-methyl-7-,8-dihydroxyisochromanone-4 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101016290A (en) * | 2007-03-01 | 2007-08-15 | 中国药科大学 | Method of synthesizing 3-methyl-7-,8-dihydroxyisochromanone-4 |
Non-Patent Citations (2)
| Title |
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| 《高等学校化学学报》 19931031 彭红等 三氟乙酸酐催化的Friedel-Crafts酰化反应--4-乙基-2,5-二甲氧基苯基烷基酮的合成 1380-1382 第14卷, 第10期 * |
| 彭红等: "三氟乙酸酐催化的Friedel-Crafts酰化反应——4-乙基-2,5-二甲氧基苯基烷基酮的合成", 《高等学校化学学报》, vol. 14, no. 10, 31 October 1993 (1993-10-31), pages 1380 - 1382 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103570665A (en) * | 2012-07-23 | 2014-02-12 | 中国药科大学 | Enantiomers of 3-methyl-7, 8-dihydroxy-isochroman-4-one, and applications thereof in controlling cardiovascular diseases |
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