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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: 2012-03-14
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]2, the preparation of 4-dihydroxy-6-methylbenzoic acid methyl ester (II, R 1 for 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 was complete, diketene (37g, 0.45mol) was added dropwise at this temperature in ether solution , After the addition, react at room temperature for 3-4h, when the reaction system turns into a yellow turbid liquid. Terminate the reaction, add the reaction liquid to 500ml of ice-water mixture, separate the ether layer, extract the water layer twice with 50ml of ether, combine the ether layers, wash with saturated brine, and dry over anhydrous magnesium sulfate. Filtration, rotary evaporation to remove diethyl ether, the residue was passed through the column with petroleum ether: ethyl acetate = 8:1 to obtain 35 g of white solid which was the target product (yield 45%).

[0044] 1 H-NMR (400M, DMSO-d 6 ): δ(ppm) 2.26(s, 3H), 3.78(s,...

Embodiment 2

[0046] 2, the preparation of 4-dimethoxy-6-methylbenzoic acid methyl ester (III, R 1 , R 2 both methyl)

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

[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] Methyl 2,4-dimethoxy-6-bromomethylbenzoate (IV, R 1 , R 2 Both are methyl, X is bromine)

[0051] Compound III (10g, 0.0476mol) was dissolved in 50ml of carbon tetrachloride, under nitrogen protection, 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 was complete, reflux Reaction 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 invention relates to the technical field of synthesizing kalinin, in particular to a total synthesis method of kalinin and structural analogs thereof. Background technique [0002] Pigeon pea (Cajanus cajan L.) is a plant of the genus Cajanus cajan L., which has a wide range of medicinal values. The main functions of pigeon pea seeds are to treat liver and kidney edema, bloody stranguria, and bleeding from hemorrhoids. Moisture hemostasis, pain relief, insecticide and other effects, mainly cure sore throat, bleeding from hemorrhoids, bloody edema, dysuria, etc. Pigeon leaf has the effect of detoxifying and reducing swelling, and is mainly used to treat children with chickenpox, carbuncle and sore. Pigeon leaves contain a large amount of stilbene compounds, such as kalin, kalin A, and kalin C (chemical structure such as figure 1 shown), these compounds have a wide range of pharmacological effects, such as anti-osteoporosis, stilbene extracts can e...

Claims

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Application Information

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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
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