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Synthetic method for cannabinol compound

A synthetic method and compound technology, applied in the field of synthesis of cannabinol compounds, can solve the problems of high reagent price, lengthy steps, and low efficiency, and achieve the effects of high atom utilization, simple operation, and high reaction efficiency

Active Publication Date: 2017-05-10
NORTHWEST UNIV(CN)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main problem at present is that the steps of extraction and separation from plants are lengthy and inefficient, so it will become a trend to seek to replace natural extraction with organic synthesis
Most of the existing synthetic pathways of cannabinol have the disadvantages of low yield, severe reaction conditions, and high price of reagents. Therefore, it is of great significance to find a simple and efficient method for synthesizing cannabinol and its analogues.

Method used

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  • Synthetic method for cannabinol compound
  • Synthetic method for cannabinol compound
  • Synthetic method for cannabinol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The synthetic route of embodiment 1 cannabinol is as follows:

[0023]

[0024] Compound 2 Synthesis

[0025] In a 50mL single-necked flask, 3,5-dihydroxypentylbenzene (1.80g, 10 mmol), 4-methylbenzyl bromide (1.85g, 10 mmol), K 2 CO 3 (1.38g, 10 mmol), acetone 30ml, and the reaction mixture was stirred evenly at room temperature. React at 50° C. for 14 h, and detect the reaction with a TLC plate until the reaction of the raw materials is complete. Concentration under reduced pressure, separation by column chromatography, petroleum ether / ethyl acetate as eluent at 10:1, to obtain product 2 (2.28g, 80%)

[0026] IR (KBr): 3032, 2917, 2411, 1462, 1387, 1127, 1055, 932, 776 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.32 – 7.30 (m, 2H), 7.20 – 7.18 (m, 2H), 6.41 (s, 1H),6.30 – 6.27 (m, 2H), 4.96 (s, 2H), 4.84 (s, 1H), 2.68 – 2.44 (m, 2H), 2.36 (s, 3H), 1.72 – 1.48 (m, 2H), 1.29 – 1.25 (m, 4H), 0.88 (t, J = 6.6 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) 13 C NMR (100...

Embodiment 2

[0044] Add palladium trifluoroacetate or palladium acetate (10 mmol%) into a 10 mL single-necked flask, seal the rubber stopper and evacuate, replace the air in the bottle with an oxygen balloon, and fill the bottle with oxygen. Then, hexafluoroisopropanol (10.0 mL) was sequentially added to the flask via a syringe under an oxygen atmosphere, and the reaction mixture was stirred homogeneously at room temperature. Add Ia (1mmol) to the well-stirred flask, react at room temperature for 24h (reaction time and temperature are determined by different substrates), TLC plate detection reaction, until the reaction of raw materials is complete. The coupling product IIa was separated by column chromatography (yield 75%) as a white solid; melting point: 151-152°C. IIa

[0045]

[0046] IR (KBr):2922, 1728, 1620, 1464, 1379, 1196, 1049, 773, 592cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 8.54 – 8.53 (m, 1H), 8.01 (d, J = 7.9 Hz, 1H),7.93 (d, J =1.8 Hz, 1H),7.82 (td, J = 7.8, 1.7 Hz...

Embodiment 3

[0049] Add palladium trifluoroacetate or palladium acetate (10 mmol%) into a 10 mL single-necked flask, seal the rubber stopper and evacuate, replace the air in the bottle with an oxygen balloon, and fill the bottle with oxygen. Then, hexafluoroisopropanol (10.0 mL) was sequentially added to the flask via a syringe under an oxygen atmosphere, and the reaction mixture was stirred homogeneously at room temperature. Add Ib (1mmol) to the well-stirred flask, react at room temperature for 24h (the reaction time and temperature are determined by different substrates), and check the reaction with a TLC plate until the raw materials are completely reacted. The coupling product IIb was separated by column chromatography (yield 80%). White solid; melting point: 205-206 ℃.

[0050]

[0051] IR (KBr): 3435, 2960, 1687, 1603, 1379, 1257, 1174, 1111, 1022, 806,590 cm -1 1 H NMR (400 MHz, CDCl 3 ) δ 8.43 – 8.28 (m, 1H), 8.01 (d, J = 7.2 Hz,1H), 7.72 (d, J = 7.9 Hz, 1H), 7.66 – 7.58...

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Abstract

The invention discloses a synthetic method for a cannabinol compound. The synthetic method comprises the following steps: subjecting two aryl carbon-hydrogen bonds to direct coupling by one step so as to synthesize a 6H-benzo[c]chromene compound with 3,5-dihydroxypentylbenzene as a starting material, palladium acetate as a catalyst and oxygen as an oxidant under the protections of phenolic hydroxyl benzyl and 2-pyridylsulfonyl, and carrying out oxidation, deprotection and methylation so as to synthesize cannabinol with high yield. The method provided by the invention realizes that direct oxidation and aryl coupling through C-H bond activation are used as the key steps of synthesizing the cannabinol, so highly-efficient and simple synthesis of the cannabinol is realized. Compared with a traditional method, the method provided by the invention has the advantages of simple operation, higher reaction yield, environment friendliness and high atom utilization rate.

Description

technical field [0001] The invention relates to a synthesis method of cannabinol compounds, belonging to the technical field of organic synthesis. Background technique [0002] Cannabinoids are the main active ingredients in cannabis, and cannabis has a wide range of natural pharmacological effects. The mechanism of action of cannabinoids is to regulate the function of immune cells and the production of cytokines by binding to the inhibitory G protein-coupled receptors CB1 and CB2 on the surface of immune cells. Previously, a large number of research results have shown that a series of compounds in cannabis have good pharmacological and physiological activities. Cannabidiol is an anesthetic drug with the molecular formula C 21 h 26 o 2 . It exists in cannabis leaves and has anti-asthma, analgesic, anti-spasmodic, calming and other activities. Cannabidiol and its analogs are a class of compounds with good pharmacological activity, and many of them have entered clinical ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/80
CPCY02P20/55C07D311/80
Inventor 王永强郭冬冬
Owner NORTHWEST UNIV(CN)
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