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A kind of cycloalkyl-containing β-hydroxyl sulfone compound and its synthesis method

A synthetic method and cycloalkyl-containing technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as low yield, achieve good substrate universality, step economy, Simple operation effect

Active Publication Date: 2021-06-18
LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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  • Abstract
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Problems solved by technology

However, usually when free radicals attack methylene cycloalkane compounds to realize the difunctionalization reaction of olefins, the cycloalkyl group is easy to undergo ring-opening reaction. Therefore, almost no cycloalkyl-containing products are generated, even if there is a small amount of cycloalkane-containing products. The product of the base is formed, and its yield is also low

Method used

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  • A kind of cycloalkyl-containing β-hydroxyl sulfone compound and its synthesis method
  • A kind of cycloalkyl-containing β-hydroxyl sulfone compound and its synthesis method
  • A kind of cycloalkyl-containing β-hydroxyl sulfone compound and its synthesis method

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[0039] This embodiment provides a method for synthesizing cycloalkyl-containing β-hydroxysulfone compounds. A cycloalkyl group with a relatively large tension can be introduced into the β-hydroxysulfone compounds. The method specifically includes the following steps:

[0040] Add methylene cycloalkane compounds, sulfonyl chloride, photocatalyst, base and solvent in sequence in the reactor, and react with stirring at room temperature under visible light irradiation;

[0041] After the reaction, the solvent was removed with a rotary evaporator to obtain a crude product, which was obtained through column chromatography, wherein the eluent was a mixed solvent of petroleum ether and ethyl acetate.

[0042] Preferably, the solvent in the above synthesis method is N,N-dimethylformamide, dimethyl sulfoxide, dichloromethane, acetonitrile, 1,4-dioxane, 1,2-dichloroethane, tetrahydrofuran, A mixture of one or more of ethanol or methanol with water. In the experiment, it was found that s...

Embodiment 1

[0055]

[0056] The reactor was placed under nitrogen, and 0.2mmol (41.2mg) methylenecyclopropane 1a, 0.3mmol (52.8mg) benzenesulfonyl chloride 2a, 2% (3.0mg) [Ru(bpy) 3 ]Cl 2 ·6H 2 O, 0.3 mmol (52.2 mg) K 2 HPO 4 , 1mL acetonitrile / water (30 / 1), under the irradiation of 12W blue light LEDs, stir at room temperature for 3h; The solvents were mixed to obtain 56.8 mg of cyclopropyl-containing β-hydroxysulfone compound 3aa (diphenyl(1-(phenylsulfonyl)cyclopropyl)methanol), with an isolated yield of 78%.

[0057] see figure 1 , figure 2 , the characterization data of compound 3aa are as follows:

[0058] 1 H NMR (400MHz, CDCl 3 )δ7.47-7.42(m,1H),7.40-7.37(m,4H),7.36-7.32(m,2H),7.24-7.20(m,2H),7.13-7.05(m,6H),5.76( s,1H),1.74-1.71(m,2H),1.08-1.04(m,2H). 13 CNMR (100MHz, CDCl 3 ) δ 142.2, 140.6, 132.8, 128.6, 128.5, 127.6, 127.5, 127.4, 79.0, 49.2, 10.6.

Embodiment 2

[0060]

[0061] The reactor was placed under nitrogen, and 0.2mmol (41.2mg) methylenecyclopropane 1a, 0.3mmol (57.2mg) p-toluenesulfonyl chloride 2b, 2% (3.0mg) [Ru(bpy) 3 ]Cl 2 ·6H 2 O, 0.3 mmol (52.2 mg) K 2 HPO 4 , 1mL acetonitrile / water (30 / 1), under the irradiation of 12W blue light LEDs, stir at room temperature for 3h; The solvents were mixed to obtain 68.0 mg of cyclopropyl-containing β-hydroxyl sulfone compound 3ab (diphenyl(1-tosylcyclopropyl)methanol), with an isolated yield of 90%.

[0062] see image 3 , Figure 4 , the characterization data of compound 3ab are as follows:

[0063] 1 H NMR (400MHz, CDCl 3 )δ7.39-7.36(m,4H),7.22(d,J=8.4Hz,2H),7.14-7.05(m,6H),7.00(d,J=8.0Hz,2H),5.78(s,1H ),2.37(s,3H),1.71-1.67(m,2H),1.05-0.91(m,2H). 13 C NMR (100MHz, CDCl 3 ) δ 143.8, 142.4, 137.5, 129.2, 128.6, 127.7, 127.5, 127.2, 79.0, 49.1, 21.5, 10.5.

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Abstract

The invention discloses a cycloalkyl-containing β-hydroxyl sulfone compound and a synthesis method thereof. The clean and sustainable visible light is used as an energy source, and the methylene cycloalkane compound is used as a substrate to realize bifunctionalization with sulfonyl chloride. The reaction of cycloalkyl-containing β-hydroxyl sulfones was synthesized. The reaction conditions of this synthesis method are mild, and the cycloalkyl groups with large tension in the reaction are retained, which provides an effective idea for the design and synthesis of drugs. The synthetic method has simple operation, good substrate universality and step economy.

Description

technical field [0001] The disclosure of the invention relates to the technical field of organic chemical synthesis, in particular to a cycloalkyl-containing β-hydroxyl sulfone compound and a synthesis method thereof. Background technique [0002] β-Hydroxysulfone compounds are common intermediates in organic synthesis and are important skeletons in many biologically active asymmetric molecules. Some anticancer drugs as well as antifungal drugs also contain β-hydroxysulfone compounds. Therefore, the synthesis of such compounds is of great significance. [0003] Methylenecycloalkanes have both cycloalkyl and exocyclic double bonds, and have been extensively studied in organic synthesis. Due to the large ring tension of cycloalkyl, it is very easy to be attacked by nucleophiles to open the ring, so it plays an important role in organic synthesis reactions. If the drug contains a cycloalkyl group, it can increase the efficacy of the drug, improve the degree of dissociation o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/00C07C317/20
CPCC07C315/00C07C317/20C07C2601/02C07C2601/04
Inventor 王贺李蕾周明东刘闯杨艳杰
Owner LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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