CN107033112A - A kind of preparation method of nevadensin - Google Patents
A kind of preparation method of nevadensin Download PDFInfo
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- CN107033112A CN107033112A CN201710337679.7A CN201710337679A CN107033112A CN 107033112 A CN107033112 A CN 107033112A CN 201710337679 A CN201710337679 A CN 201710337679A CN 107033112 A CN107033112 A CN 107033112A
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- nevadensin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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Abstract
A kind of preparation method for nevadensin that the present invention is provided, has the feature that, including following preparation process：Step one, phloroglucin and acetic anhydride are used for reaction raw materials, Friedel-Crafts reactions are carried out under the catalysis of BFEE, 2,4,6 trihydroxy-acetophenones are obtained；Step 2,2 that step one is obtained and carry out annulation at 4,6 trihydroxy-acetophenones to methoxybenzene acyl chlorides under the catalysis of potassium carbonate, obtain the methoxy flavone of 5,7 dihydroxy 4 '；Step 3,5 that step 2 is obtained, the methoxy flavone of 7 dihydroxy 4 ' carries out radical reaction under NBS catalysis, obtains the methoxy flavone of 5,76,8 dibromo of dihydroxy 4 '；Step 4,5 that step 3 is obtained, the methoxy flavone of 76,8 dibromo of dihydroxy 4 ' and sodium methoxide carry out methoxylation under the catalysis of cuprous bromide, obtain nevadensin.
Description
Technical field
The invention belongs to organic chemistry filed, and in particular to a kind of preparation method of nevadensin.
Background technology
Nevadensin, alias lysionotin, the effects such as with good cough-relieving, anti-inflammatory.Modern pharmacological research shows, lysiontus pauciflorus
Element is primarily present in Lysionotus carnosus Hemsl. (Lysionotus pauciflorus Maxim.), and the main method for obtaining nevadensin is exactly to enter from Gesneriaceae Lysionotus carnosus Hemsl. (Lysionotus pauciflorus Maxim.)
Row is extracted.
At present, lysiontus pauciflorus is purified by said extracted method and have many deficiencies.Zhou Faxing etc., which discloses first water and boiled, to be removed
Water impurity, alcohol reflux is extracted, then the technique through silica gel post separation, but the process energy consumption is big.In addition, LiuY etc. is used
Methanol is extracted, extracting n-butyl alcohol, extract gel (Sephadex HL-20) column chromatography, chloroform elution fraction use concentration,
The method of standing obtains yellow needles nevadensin, but this method Poisoning consumption of organic solvent is big, and prepare
The yield of nevadensin is small.
The content of the invention
The present invention is carried out to solve the above problems, it is therefore intended that provide a kind of preparation method of nevadensin.
The invention provides a kind of preparation method of nevadensin, have the feature that, including following preparation process：Step
Rapid one, phloroglucin and acetic anhydride are used for reaction raw materials, and Friedel-Crafts are carried out under the catalysis of BFEE
Reaction, obtains 2,4,6- trihydroxy-acetophenones；Step 2,2 that step one is obtained, 4,6- trihydroxy-acetophenones and to methoxyl group
Benzoyl chloride carries out annulation under the catalysis of potassium carbonate, obtains 5,7- -4 '-methoxy flavones of dihydroxy；Step 3, by step
Two obtained -4 '-methoxy flavones of 5,7- dihydroxy carry out radical reaction under NBS catalysis, obtain 5,7- dihydroxy -6,
The bromo- 4 '-methoxy flavones of 8- bis-；Step 4, the bromo- 4 '-methoxy flavone of 5,7- dihydroxy -6,8- bis- that step 3 is obtained and
Sodium methoxide carries out methoxylation under the catalysis of cuprous bromide, obtains nevadensin.
In the preparation method for the nevadensin that the present invention is provided, it can also have the feature that：Wherein, step one
Friedel-Crafts reactions include following sub-step：Step 1-1, in molar ratio number weigh 1 part of phloroglucin, 2.4 portions of vinegar
Acid anhydrides and organic solvent I, are added in the first three-necked flask, then weigh 1.2 parts of BFEEs the one or three mouthful of burning is added dropwise
In bottle, mixed liquor I is obtained；Step 1-2, stirring reaction 10 hours under the conditions of 50 ° of mixed liquor I, reaction solution I；Step 1-3, instead
Answer liquid I to remove organic solvent I by rotating, then recrystallized by water, obtain the trihydroxy-acetophenone of yellow crystals 2,4,6-.
In the preparation method for the nevadensin that the present invention is provided, it can also have the feature that：Wherein, in step 1-
In 1, organic solvent I is ethyl acetate, and the addition of the ethyl acetate is to add 0.50ml acetic acid second per 1mmol phloroglucins
Ester.
In the preparation method for the nevadensin that the present invention is provided, it can also have the feature that：Wherein, step 2
Annulation includes following sub-step：Step 2-1, under nitrogen protection, number weighs 1 part 2,4,6- trihydroxy benzenes in molar ratio
Ethyl ketone, 10 parts of potassium carbonate and organic solvent II, add the second three-necked flask in, at room temperature stir 10 minutes, then weigh 1.5 parts it is right
Methoxybenzene acyl chlorides is added in the second three-necked flask, obtains mixed liquor II；Step 2-2, mixed liquor II is stirred under the conditions of 60 DEG C
Reaction 24 hours, is cooled under room temperature condition and obtains reaction solution II；Step 2-3, reaction solution II is after suction filtration and acetone washing
Obtain filtrate I；Step 2-4, filtrate I is extracted three times by ethyl acetate, washed, saturated nacl aqueous solution is washed, anhydrous slufuric acid
Sodium obtains solid powder I after drying and rotating removal ethyl acetate；Step 2-5, uses volume ratio for hexane：Ethyl acetate=4:
1 solution carries out column chromatography to solid powder I, obtains solid powder 5,7- -4 '-methoxy flavones of dihydroxy.
In the preparation method for the nevadensin that the present invention is provided, it can also have the feature that：Wherein, step 2-1
In, organic solvent II is acetone, and the addition of the acetone is that, per 1mmol2,4,6- trihydroxy-acetophenones add 1.68ml acetone.
In the preparation method for the nevadensin that the present invention is provided, it can also have the feature that：Wherein, step 3
Radical reaction includes following sub-step：Step 3-1, in molar ratio number weigh 1 part of 5,7- -4 '-methoxy flavone of dihydroxy
With organic solvent III, add in the 3rd three-necked flask, then weigh 2 parts of NBS and be slowly added in the 3rd three-necked flask, mixed
Liquid III；Step 3-2, stirring reaction 5 hours at ambient temperature of mixed liquor III, obtains reaction solution III；Step 3-3, by reaction solution
III pours into frozen water, and precipitation obtains solid II；Step 3-4, solid II passes through suction filtration and washing, obtains green filter cake II；Step
3-5, uses volume ratio for ether：Ethyl acetate=4:1 solution carries out column chromatography to filter cake II, obtains yellow solid 5,7- bis-
The bromo- 4 '-methoxy flavone of hydroxyl -6,8- bis-.
In the preparation method for the nevadensin that the present invention is provided, it can also have the feature that：Wherein, step 3-1
In, organic solvent III is trifluoroacetic acid, and the addition of the trifluoroacetic acid is that, per 1mmol5,7- -4 '-methoxy flavones of dihydroxy add
Enter 2.82ml trifluoroacetic acids.
In the preparation method for the nevadensin that the present invention is provided, it can also have the feature that：Wherein, step 4
Methoxylation includes following sub-step：Step 4-1, in molar ratio number weigh 1 part of cuprous bromide and 1000 parts of sodium methoxides,
Add in the 4th three-necked flask, stirring to solution in the 4th three-necked flask becomes au bleu；Step 4-2, in molar ratio number claim
100 parts of bromo- 4 '-methoxy flavones of 5,7- dihydroxy -6,8- bis- are taken to be dissolved in organic solvent IV, under nitrogen protection, dropwise
Add in the 4th three-necked flask, obtain mixed liquor IV；Step 4-3, mixed liquor IV is under 120 DEG C and 700W power conditions, microwave
1 hour is reacted, reaction solution IV is obtained；Step 4-4, the temperature of question response liquid IV is down to after room temperature, with the salt that mass concentration is 5%
The PH of aqueous acid regulation reaction solution IV obtains filtrate III to 6, then through suction filtration；Step 4-5, filtrate III extracts by ethyl acetate
Take, anhydrous sodium sulfate drying and revolving remove the crude product that yellow oily is obtained after ethyl acetate；Step 4-6, using volume ratio
For ether：Ethyl acetate=3：1 solution carries out column chromatography to crude product, obtains yellow solid nevadensin.
In the preparation method for the nevadensin that the present invention is provided, it can also have the feature that：Wherein, step 4-1
In, sodium methoxide is slowly added in excessive methanol by metallic sodium and is stirred at room temperature and prepares, and the addition of the methanol is every
1mmol metallic sodiums add 1.1ml methanol.
In the preparation method for the nevadensin that the present invention is provided, it can also have the feature that：Wherein, step 4-2
In, organic solvent IV is DMF, and the addition of the DMF is that, per 1mmol5, the bromo- 4 '-methoxy flavone of 7- dihydroxy -6,8- bis- adds
Enter 17.70ml DMF.
The effect of invention and effect
The preparation method of a kind of nevadensin provided according to the present invention, because the preparation method of the nevadensin is chemistry
Total synthesis method, compared to traditional plant extracting method, this method make it that the preparation technology for obtaining nevadensin is simple, energy consumption drop
Low, yield is high and environment-friendly.Further, since the relatively low phloroglucin of price is employed as raw material, compared to traditional plant
Extracting method, this method causes the preparation cost reduction for preparing nevadensin.
Brief description of the drawings
Fig. 1 is the chemical reaction process that nevadensin is prepared in embodiments of the invention.
Embodiment
In order that the technological means that the present invention is realized is easy to understand with effect, following examples combination accompanying drawing is to this hair
It is bright to be specifically addressed.
<Embodiment>
Fig. 1 is the chemical reaction process that nevadensin is prepared in embodiments of the invention.
As illustrated, preparing nevadensin I by full chemistry synthetic method, step is as follows：
Step one, 2,4,6- trihydroxy-acetophenones II, including following sub-step are prepared by Friedel-Crafts reactions：
Step 1-1, weighs 79.7mmol (10g) phloroglucin, 190mmol (19.4g) acetic anhydride and 40ml ethyl acetate,
Add in the first three-necked flask, then weigh 97.2mmol (13.8g) BFEE and be added dropwise in the first three-necked flask, obtain
To mixed liquor I.
Step 1-2, stirring reaction 10 hours under the conditions of 50 ° of mixed liquor I, reaction solution I.
Step 1-3, reaction solution I removes ethyl acetate by rotating, then is recrystallized by water, obtains 14.5g yellow crystals.
The structural characterization data of yellow crystals are as follows in this step：1H-NMR (400MHZ, CDCl3, δ ppm):12.23(s,
2H),10.38(s,1H),5.79(s,2H),2.50(s,3H)。
As a result it is 2,4,6- trihydroxy-acetophenones II, in the present embodiment, 2,4,6- trihydroxy benzenes to show the yellow crystals
The yield of ethyl ketone II is 86%.
Step 2, -4 '-methoxy flavone of 5,7- dihydroxy III, including following sub-step are prepared by annulation：
Step 2-1, under nitrogen protection, weighs the trihydroxy-acetophenones II of 59.5mmo (l10g) 2,4,6-, 594.7mmol
(82.2g) potassium carbonate and 100ml acetone, are added in the second three-necked flask, are stirred 10 minutes at room temperature, then weigh 89.2mmol
(15.2g) is added in the second three-necked flask to methoxybenzene acyl chlorides, obtains mixed liquor II.
Step 2-2, stirring reaction 24 hours under the conditions of 60 DEG C of mixed liquor II are cooled under room temperature condition and obtain reaction solution
Ⅱ。
Step 2-3, reaction solution II obtains filtrate I after suction filtration and acetone washing.
Step 2-4, filtrate I is extracted three times by 200ml ethyl acetate, washed, saturated nacl aqueous solution is washed, anhydrous sulphur
Sour sodium obtains solid powder I after drying and rotating removal ethyl acetate.
Step 2-5, uses volume ratio for hexane：Ethyl acetate=4:1 solution carries out column chromatography to solid powder I, obtains
To 12g solid powders.
The structural characterization data of solid powder are as follows in this step：1H-NMR (400MHZ, DMSO, δ ppm):8.02-8.09
(m, 2H), 7.88-7.92 (m, 2H), 6.96-7.11 (m, 2H), 6.29 (s, 1H), 3.56 (s, 3H), 2.63 (s, 1H), 2.07
(s,1H)。
As a result it is -4 '-methoxy flavone of 5,7- dihydroxy III, in the present embodiment, 5, the 7- bis- to show the solid powder
Hydroxyl -4 '-methoxy flavone III yield be 71%.
Step 3, the bromo- 4 '-methoxy flavone IV of 5,7- dihydroxy -6,8- bis- is prepared by radical reaction, including as follows
Sub-step：
Step 3-1, weighs -4 '-methoxy flavone of 35.4mmol (10g) 5,7- dihydroxy III and 100ml trifluoroacetic acids, plus
Enter in the 3rd three-necked flask, then weigh 70.9mmol (12.6g) NBS and be slowly added in the 3rd three-necked flask, obtain mixed liquor
Ⅲ。
Step 3-2, stirring reaction 5 hours at ambient temperature of mixed liquor III, obtains reaction solution III.
Step 3-3, reaction solution III is poured into frozen water, and precipitation obtains solid II.
Step 3-4, solid II passes through suction filtration and washing, obtains green filter cake II.
Step 3-5, uses volume ratio for ether：Ethyl acetate=4:1 solution carries out column chromatography to filter cake II, obtains
14.5g yellow solids.
The structural characterization data of yellow solid are as follows in this step：1H-NMR (400MHZ, DMSO, δ ppm):10.81(s,
1H), 10.37 (s, 1H), 7.93 (d, 2H), 6.93 (d, 2H), 6.49 (s, 1H), 3.83 (s, 3H).
As a result show, the yellow solid is the bromo- 4 '-methoxy flavone IV of 5,7- dihydroxy -6,8- bis-, in the present embodiment
In, the yield of the bromo- 4 '-methoxy flavone IV of 5,7- dihydroxy -6,8- bis- is 94%.
Step 4, nevadensin I, including following sub-step are prepared by methoxylation：
Step 4-1,25ml methanol is added in the 4th three-necked flask, 22.6mmol (0.522g) metallic sodium is slowly added to,
It is stirred at room temperature.Treat that bubble-free is produced, add 0.0227mmol (0.0036g) cuprous bromide, stir at room temperature to the four or three mouthful
Solution becomes au bleu in flask.
Step 4-2, weighs the bromo- 4 '-methoxy flavone IV of 2.26mmol (1g) 5,7- dihydroxy -6,8- bis- and is dissolved in
In 40mlDMF, under nitrogen protection, it is added dropwise in the 4th three-necked flask, obtains mixed liquor IV.
Step 4-3, mixed liquor IV 1 hour of microwave reaction, obtains reaction solution IV under 120 DEG C and 700W power conditions.
Step 4-4, the temperature of question response liquid IV is down to after room temperature, adjusts anti-with mass concentration for 5% aqueous hydrochloric acid solution
The PH of liquid IV is answered to obtain filtrate III to 6, then through suction filtration.
Step 4-5, filtrate III is extracted by ethyl acetate, anhydrous sodium sulfate drying and revolving are obtained after removing ethyl acetate
The crude product of yellow oily.
Step 4-6, uses volume ratio for ether：Ethyl acetate=3：1 solution carries out column chromatography to crude product, obtains
0.70g yellow solids.
The structural characterization data of yellow solid are as follows in this step：1H-NMR (400MHZ, DMSO, δ ppm)：7.58(d,
2H), 6.98 (d, 2H), 6.42 (s, 1H), 3.70-3.80 (s, 9H).
As a result show, the yellow solid is nevadensin I, the yield of nevadensin I is 90% in the present embodiment.
The effect of embodiment and effect
The preparation method of a kind of nevadensin provided according to the present embodiment, because the preparation method of the nevadensin is change
Total synthesis method is learned, compared to traditional plant extracting method, this method make it that the preparation technology for obtaining nevadensin is simple, energy consumption
Reduction, yield is high and environment-friendly.Further, since the relatively low phloroglucin of price is employed as raw material, compared to tradition plant
Thing extracting method, this method causes the preparation cost reduction for preparing nevadensin.
Nevadensin has successfully been prepared by chemical total synthesis method in the present embodiment, and has obtained higher yield.
Therefore, a kind of preparation method step for nevadensin that the present invention is provided is simple, and cost is low, and yield is high, is adapted to work
Industry metaplasia is produced.
Claims (10)
1. a kind of preparation method of nevadensin, including following preparation process：
Step one, phloroglucin and acetic anhydride are used for reaction raw materials, under the catalysis of BFEE carry out Friedel-
Crafts reacts, and obtains 2,4,6- trihydroxy-acetophenones；
Step 2, described 2 that step one is obtained, 4,6- trihydroxy-acetophenones and to methoxybenzene acyl chlorides potassium carbonate catalysis
Lower carry out annulation, obtains 5,7- -4 '-methoxy flavones of dihydroxy；
Step 3, free radical is carried out by -4 '-methoxy flavone of 5, the 7- dihydroxy that step 2 is obtained under NBS catalysis
Reaction, obtains the bromo- 4 '-methoxy flavone of 5,7- dihydroxy -6,8- bis-；
Step 4, the bromo- 4 '-methoxy flavone of 5, the 7- dihydroxy -6,8- bis- and sodium methoxide that step 3 is obtained are in bromination
Methoxylation is carried out under cuprous catalysis, nevadensin is obtained.
2. a kind of preparation method of nevadensin according to claim 1, it is characterised in that：
Wherein, the Friedel-Crafts reactions of step one include following sub-step：
Step 1-1, in molar ratio number weigh 1 part of phloroglucin, 2.4 parts of acetic anhydride and organic solvent I, add the
In one three-necked flask, then weigh 1.2 parts of BFEEs and be added dropwise in first three-necked flask, obtain mixed liquor
Ⅰ；
Step 1-2, the mixed liquor I stirring reaction 10 hours under the conditions of 50 °, obtains reaction solution I；
Step 1-3, the reaction solution I removes the organic solvent I by rotating, then is recrystallized by water, obtains yellow crystals
2,4,6- trihydroxy-acetophenones.
3. a kind of preparation method of nevadensin according to claim 2, it is characterised in that：
Wherein, in step 1-1, the organic solvent I is ethyl acetate, and the addition of the ethyl acetate is described in per 1mmol
Phloroglucin adds ethyl acetate described in 0.50ml.
4. a kind of preparation method of nevadensin according to claim 1, it is characterised in that：
Wherein, the annulation of step 2 includes following sub-step：
Step 2-1, under nitrogen protection, number weighs 1 part described 2,4,6- trihydroxy-acetophenones, 10 parts of carbon in molar ratio
Sour potassium and organic solvent II, add the second three-necked flask in, at room temperature stir 10 minutes, then weigh 1.5 parts it is described to methoxyl group
Benzoyl chloride is added in second three-necked flask, obtains mixed liquor II；
Step 2-2, the mixed liquor II stirring reaction 24 hours under the conditions of 60 DEG C, is cooled under room temperature condition and obtains reaction solution
Ⅱ；
Step 2-3, the reaction solution II obtains filtrate I after suction filtration and acetone washing；
Step 2-4, the filtrate I is extracted three times by ethyl acetate, washed, saturated nacl aqueous solution is washed, anhydrous sodium sulfate
Dry and rotate and obtain solid powder I after removing ethyl acetate；
Step 2-5, uses volume ratio for hexane：Ethyl acetate=4:1 solution carries out column chromatography to the solid powder I, obtains
To solid powder 5,7- -4 '-methoxy flavones of dihydroxy.
5. a kind of preparation method of nevadensin according to claim 4, it is characterised in that：
Wherein, in step 2-1, the organic solvent II is acetone, and the addition of the acetone is 2,4,6- tri- hydroxyls described in per 1mmol
Benzoylformaldoxime adds acetone described in 1.68ml.
6. a kind of preparation method of nevadensin according to claim 1, it is characterised in that：
Wherein, the radical reaction of step 3 includes following sub-step：
Step 3-1, in molar ratio number weigh 1 part of -4 '-methoxy flavone of 5, the 7- dihydroxy and organic solvent III, add
In 3rd three-necked flask, then weigh 2 parts of NBS and be slowly added in the 3rd three-necked flask, obtain mixed liquor III；
Step 3-2, the mixed liquor III stirring reaction 5 hours at ambient temperature, obtains reaction solution III；
Step 3-3, the reaction solution III is poured into frozen water, and precipitation obtains solid II；
Step 3-4, the solid II passes through suction filtration and washing, obtains green filter cake II；
Step 3-5, uses volume ratio for ether：Ethyl acetate=4:1 solution carries out column chromatography to the filter cake II, obtains Huang
Color solid 5, the bromo- 4 '-methoxy flavone of 7- dihydroxy -6,8- bis-.
7. a kind of preparation method of nevadensin according to claim 6, it is characterised in that：
Wherein, in step 3-1, the organic solvent III is trifluoroacetic acid, and the addition of the trifluoroacetic acid is 5 described in per 1mmol,
- 4 '-methoxy flavone of 7- dihydroxy adds trifluoroacetic acid described in 2.82ml.
8. a kind of preparation method of nevadensin according to claim 1, it is characterised in that：
Wherein, the methoxylation of step 4 includes following sub-step：
Step 4-1, in molar ratio number weigh 1 part of cuprous bromide and 1000 parts of sodium methoxides, add the four or three mouthful of burning
In bottle, stirring to solution in the 4th three-necked flask becomes au bleu；
Step 4-2, in molar ratio number weigh 100 parts of bromo- 4 '-methoxy flavones of 5, the 7- dihydroxy -6,8- bis- and be dissolved in
In organic solvent IV, under nitrogen protection, it is added dropwise in the 4th three-necked flask, obtains mixed liquor IV；
Step 4-3, the mixed liquor IV 1 hour of microwave reaction, obtains reaction solution IV under 120 DEG C and 700W power conditions；
Step 4-4, after the temperature of the reaction solution IV is down to room temperature, institute is adjusted with mass concentration for 5% aqueous hydrochloric acid solution
State the PH of reaction solution IV and obtain filtrate III to 6, then through suction filtration；
Step 4-5, the filtrate III is extracted by ethyl acetate, anhydrous sodium sulfate drying and revolving are obtained after removing ethyl acetate
The crude product of yellow oily；
Step 4-6, uses volume ratio for ether：Ethyl acetate=3：1 solution carries out column chromatography to the crude product, obtains Huang
Color solid nevadensin.
9. a kind of preparation method of nevadensin according to claim 8, it is characterised in that：
Wherein, in step 4-1, the sodium methoxide is slowly added in excessive methanol by metallic sodium and is stirred at room temperature and prepares,
The addition of the methanol is that metallic sodium adds methanol described in 1.1ml described in per 1mmol.
10. a kind of preparation method of nevadensin according to claim 8, it is characterised in that：
Wherein, in step 4-2, the organic solvent IV is DMF, the addition of the DMF be 5,7- dihydroxy described in per 1mmol-
6,8- bis- bromo- 4 '-methoxy flavones add DMF described in 17.70ml.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114057678A (en) * | 2021-12-27 | 2022-02-18 | 郑州海阔光电材料有限公司 | Synthetic method of 1-bromo-3-chlorodibenzofuran |
-
2017
- 2017-05-15 CN CN201710337679.7A patent/CN107033112A/en active Pending
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| JAMES T. ZACHARIA ET AL: "Facile synthesis of acacetin-7-O-b-D-galactopyranoside", 《CARBOHYDRATE RESEARCH》 * |
| JIN WANG ET AL: "Total synthesis of apigenin", 《JOURNAL OF CHEMICAL RESEARCH》 * |
| YUE LI ET AL: "Semisynthesis of polymethoxyflavonoids from naringin and hesperidin", 《JOURNAL OF CHEMICAL RESEARCH》 * |
| 唐才芳等: "具有抗结核活性的石吊兰素及其类似物的合成", 《药学通报》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114057678A (en) * | 2021-12-27 | 2022-02-18 | 郑州海阔光电材料有限公司 | Synthetic method of 1-bromo-3-chlorodibenzofuran |
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