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Preparation method of trans-trisubstituted alkene derivative

A tri-substituted and derivative technology is applied in the field of preparation of trans-tri-substituted alkene derivatives to achieve the effects of wide substrate range, simple post-treatment and strong reaction specificity

Active Publication Date: 2019-06-14
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the synthesis of trisubstituted alkenes is one of the important contents of organic chemistry, among which, the regio- and stereoselective synthesis of trans-trisubstituted alkenes is even more challenging.

Method used

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  • Preparation method of trans-trisubstituted alkene derivative
  • Preparation method of trans-trisubstituted alkene derivative
  • Preparation method of trans-trisubstituted alkene derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (Z)-4,4,5,5-tetramethyl-2-(2-(2-phenyl-1-(o-tolyl)vinyl)phenyl)-1,3,2-dioxa Preparation of Borolanes

[0025]

[0026] Add 0.3mmol of sodium carbonate, 0.1mmol of diphenylacetylene, 0.005mmol of palladium acetate, 0.005mmol of bis(2-diphenylphosphophenyl)ether, 0.15mmol of pinacol diborate, and 0.15mmol of 2-methyliodobenzene Add 1mL of N,N-dimethylformamide into a 15mL reaction tube, fill it with nitrogen repeatedly 10 times, place it in an oil bath at 120°C, and react for 24h; cool to room temperature, dilute the reaction solution with ethyl acetate, and wash with water Three times, the organic phase was anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by thin layer chromatography to obtain 18.6 mg of the target product with a yield of 47%. The NMR and high-resolution mass spectrometry of this compound are characterized as follows: 1 H NMR (500MHz, CDCl 3 )δ7.69-7.64 (m, 1H), 7.26-7.17 (m, 5H), 7.16-7.07 (m, 4H), 6.97-6.94 (m, 3H), 6.62 (s, IH), 2.11 (...

Embodiment 2

[0028] (Z)-2-(2-(1-(2-ethylphenyl)-2-phenylethenyl)phenyl)-4,4,5,5-tetramethyl-1,3,2- Preparation of dioxaborolane

[0029]

[0030] Add 0.3mmol of sodium carbonate, 0.1mmol of diphenylacetylene, 0.005mmol of palladium acetate, 0.005mmol of bis(2-diphenylphosphophenyl)ether, 0.15mmol of pinacol diborate, and 0.15mmol of 2-ethyl iodobenzene Add 1mL of N,N-dimethylformamide into a 15mL reaction tube, fill it with nitrogen repeatedly 10 times, place it in an oil bath at 120°C, and react for 24h; cool to room temperature, dilute the reaction solution with ethyl acetate, and wash with water Three times, the organic phase was anhydrous Na 2 SO 4 Drying, filtration, concentration, and purification by thin-layer chromatography gave 23.7 mg of the target product, with a yield of 57%. The NMR and high-resolution mass spectrometry of this compound are characterized as follows: 1 H NMR (500MHz, CDCl 3 )δ7.67(dd, J=6.9, 1.9Hz, 1H), 7.31-7.28(m, 2H), 7.25-7.19(m, 3H), 7.17-7.13(m, 1...

Embodiment 3

[0032] (Z)-2-(2-(1-(2-isopropylphenyl)-2-phenylethenyl)phenyl)-4,4,5,5-tetramethyl-1,3,2 - Preparation of dioxaborolane

[0033]

[0034]Add 0.3mmol of sodium carbonate, 0.1mmol of diphenylacetylene, 0.005mmol of palladium acetate, 0.005mmol of bis(2-diphenylphosphophenyl)ether, 0.15mmol of pinacol diborate, and 0.15mmol of 2-isopropyl iodobenzene Add 1mL of mmol and N,N-dimethylformamide into a 15mL reaction tube, fill it with nitrogen repeatedly 10 times, place it in an oil bath at 120°C, and react for 24h; cool to room temperature, dilute the reaction solution with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Drying, filtration, concentration, and purification by thin-layer chromatography gave 27.4 mg of the target product, with a yield of 64%. The NMR and high-resolution mass spectrometry of this compound are characterized as follows: 1 H NMR (500MHz, CDCl 3 )δ7.70-7.64(m, 1H), 7.36-7.29(m, 2H), 7.25-7.18(m...

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Abstract

The invention discloses a preparation method of a trans-trisubstituted alkene derivative. The preparation method comprises following steps: 1, an alkali, an alkyne, a palladium catalyst, a ligand, a halogenated aromatic hydrocarbon, a precursor compound, and an organic solvent are introduced into a reaction container, nitrogen gas is adopted for repeat filling, and reaction is carried out for 12 to 36h at 60 to 140 DEG C; 2, a product obtained in step 1 is diluted with Ethyl Acetate, is washed with water, and is separated so as to obtain an organic phase; and 3, the organic phase obtained in step 2 is subjected to drying, filtering, concentrating, and column chromatography or thin-layer chromatography processing so as to obtain the trans-trisubstituted alkene derivative. According to the preparation method, construction of one carbon boron bond is realized in construction of the trans-tri aromatic hydrocarbon-substituted alkenes, excellent zone selectivity is achieved, and the trans-trisubstituted alkene derivative which is not easily synthesized using other methods is synthesized.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of trans-trisubstituted olefin derivatives. Background technique [0002] Trisubstituted olefin is one of the basic organic structural units, and it also widely exists in natural products, new materials and bioactive substances. Tumors have obvious drug activity, and have played an active therapeutic role in the treatment of human cancer, and once became the research target of many synthetic chemists. Bioactive molecules such as vitamin A and lutein also contain multiple trisubstituted olefin structural units. In addition, bisabolene exists in natural products such as bergamot oil, parsnip root oil and myrrh, because of its special fragrance, it is widely used in food flavors and cosmetics, and bisabolene also has good antibacterial properties. Oxidative, often used in anti-oxidant and anti-inflammatory products. Therefore, the synthe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
Inventor 程国林吕薇薇
Owner HUAQIAO UNIVERSITY
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