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Cycloalkyl-containing beta-hydroxy sulfone compound and synthesis method thereof

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, The effect of mild reaction conditions

Active Publication Date: 2019-11-22
LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Cycloalkyl-containing beta-hydroxy sulfone compound and synthesis method thereof
  • Cycloalkyl-containing beta-hydroxy sulfone compound and synthesis method thereof
  • Cycloalkyl-containing beta-hydroxy sulfone compound and synthesis method thereof

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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 adjusted with a rotary evaporator to obtain a crude product, and the crude product was subjected to column chromatography to obtain the product, 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 ...

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), irradiated by 12W blue light LEDs, stirred at room temperature for 3h; solvent 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), irradiated by 12W blue light LEDs, stirred at room temperature for 3h; solvent 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 beta-hydroxyl sulfone compound and a synthesis method thereof. Clean and sustainable visible light is used as an energy source; a methylene naphthenic compound is used as a substrate; according to the present invention, the bifunctional reaction with sulfonyl chloride is achieved, so that the cycloalkyl-containing beta-hydroxy sulfone compound is synthesized; the reaction condition of the synthesis method is mild, the cycloalkyl having the large tension in the reaction is retained, the effective idea is provided for the design and the synthesis of the drug, and the synthesis method has characteristics of 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 Applications(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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