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Preparation method of cajanin and substance with similar structure

A technology similar to kalinin, which is applied in the preparation of organic compounds, preparation of oxygen-containing compounds, chemical instruments and methods, etc., can solve the problems of no literature reports on the total synthesis of kalinin and its structural analogues

Active Publication Date: 2015-05-27
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although kalinolin has such a wide range of pharmacological effects, there are no reports on the total synthesis of kalinin and its structural analogues at home and abroad so far.

Method used

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  • Preparation method of cajanin and substance with similar structure
  • Preparation method of cajanin and substance with similar structure
  • Preparation method of cajanin and substance with similar structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of 2,4-Dihydroxy-6-methylbenzoic acid methyl ester (II, R 1 Is methyl)

[0043] Methyl acetoacetate (50g, 0.43mol) was dissolved in 300ml of ether, NaH (15.50g 0.45mol, 70%) was added at room temperature, after the addition, at this temperature, the ether solution of diketene (37g, 0.45mol) was added dropwise After the addition, react at room temperature for 3-4 hours, at which time the reaction system becomes yellow turbid liquid. The reaction was terminated, the reaction solution was added to 500 ml of ice-water mixture, the ether layer was separated, the water layer was extracted twice with 50 ml of ether, the ether layers were combined, washed with saturated brine, and dried overnight with anhydrous magnesium sulfate. Filtration, rotary evaporation to remove the ether, the residue was passed through the column with petroleum ether: ethyl acetate = 8:1 to obtain 35 g of white solid as the target product (yield 45%).

[0044] 1 H-NMR(400M, DMSO-d 6 ): δ (ppm) ...

Embodiment 2

[0046] Preparation of 2,4-Dimethoxy-6-methylbenzoic acid methyl ester (III, R 1 , R 2 All methyl)

[0047] Compound II (12g, 0.066mol) was dissolved in 50ml of acetone, potassium carbonate (27.3g, 0.198mol), methyl iodide (28g, 0.198mol) were added, and the reaction was heated and refluxed for 3h. The reaction was stopped. The reaction solution was added to 100ml of water and acetic acid Extract with ethyl ester (3*50ml), combine the organic layers, and wash the organic layers with 10% sodium hydroxide solution, 10% hydrochloric acid, and saturated brine in sequence. The organic layer was dried with anhydrous magnesium sulfate. After filtration, the solvent was removed by rotary evaporation to obtain a colorless oil, which was recrystallized with petroleum ether / ethyl acetate to obtain 13.5 g of colorless crystals (yield 97%).

[0048] 1 H-NMR(400M, CDCl 3 ): δ(ppm) 2.28(s, 3H), 3.80(s, 6H), 3.88(s, 3H), 6.31(s, 2H).

Embodiment 3

[0050] 2,4-Dimethoxy-6-bromomethyl methyl benzoate (IV, R 1 , R 2 All are methyl, X is bromine)

[0051] Compound III (10g, 0.0476mol) was dissolved in 50ml of carbon tetrachloride, protected by nitrogen, heated to reflux, and a mixture of NBS (8.5g, 0.0476mol) and BPO (0.11g, 0.476mmol) was added in batches. After the addition, reflux Reaction for 1h. The reaction was stopped, cooled, filtered, and the filtrate was spin-dried to obtain a light yellow solid, which was recrystallized from absolute ethanol to obtain 11.3 g of a white solid (yield 82%).

[0052] 1 H-NMR(400M, CDCl 3 ): δ (ppm) 3.85 (s, 3H), 3.93 (s, 3H), 3.96 (s, 3H), 4.66 (s, 2H), 6.47 (s, 1H), 6.74 (s, 1H).

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Abstract

The invention discloses a preparation method of cajanin and substances with a similar structure. According to the invention, acyl acetate and diketene are subject to a condensation reaction, such that an intermediate compound II is obtained; the intermediate compound II is subject to an alkylation reaction and a halogenation reaction, such that an intermediate compound IV is obtained; the intermediate compound IV is subject to a condensation reaction with an organic phosphine reagent, and is subject to a witting reaction, such that a compound VI is obtained; the compound VI is subject to a dehydrocarbylation and pentanol iosprene conversion reaction, and the reactant is hydrolyzed or alcoholyzed, such that cajanin I and substances with the similar structure are obtained. According to the invention, cajanin and substances with the similar structure are prepared through a chemical synthetic method. The technical process adopted by the synthetic route is easy to operate, the yield is good, and the product purity is high. The method provided by the invention assists in providing a basis for further researches, developments and applications of various pharmacologic actions of cajanin.

Description

Technical field [0001] The present invention relates to the technical field of synthesizing xylin, in particular to a total synthesis method of xylin and its structural analogs. Background technique [0002] Cajanus cajan L. is a plant of the genus Cajanus cajan in the legume family. It has a wide range of medicinal values. The main functions of Cajanus cajan L. seeds are the treatment of liver and kidney edema, hemorrhage, blood under hemorrhoids, etc. Moisture hemostasis, analgesic, insecticide and other effects, mainly treat sore throat, blood under hemorrhoids, hemorrhage and edema, dysuria, etc. Pigeon pea leaves have the effect of detoxification and swelling, and are mainly used to treat children's chickenpox and carbuncle. Pigeon pea leaves contain a large number of stilbene compounds, such as coumarin, coumarin A, and coumarin C (chemical structure such as figure 1 (Shown), this type of compound has a wide range of pharmacological effects, such as anti-osteoporosis, stil...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C65/28C07C51/09C07C27/02
Inventor 季兴跃李卓荣薛司徒
Owner MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI