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Synthesizing method of fused-ring aryl substituted formaldehyde compound

A fused-ring aryl group and synthesis method technology, which is applied in the field of synthesis of aldehyde compounds, can solve the problems of difficult control of regioselectivity, difficulty in obtaining raw materials, and low practical value, and achieve a wide application range, simple operation, and mild conditions. Effect

Active Publication Date: 2016-05-25
HENAN NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first approach is to introduce formyl (aldehyde) regioselectively into the α-position of the naphthalene ring to synthesize 1-naphthaldehyde. The disadvantage of this method is that the regioselectivity is difficult to control, and the obtained is often different body mixture
The second approach is to convert other original functional groups on the α position of the naphthalene ring into an aldehyde group to synthesize 1-naphthaldehyde. The disadvantage of this method is that the raw materials are not easy to obtain
The disadvantage of this synthetic method is that the raw materials are not easy to obtain and there are many reaction steps, so the practical value is low

Method used

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  • Synthesizing method of fused-ring aryl substituted formaldehyde compound
  • Synthesizing method of fused-ring aryl substituted formaldehyde compound
  • Synthesizing method of fused-ring aryl substituted formaldehyde compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015]

[0016] Add 1a (0.5mmol, 80mg) and dichloromethane (2mL) to a 10mL round bottom flask, then add ICl (1mmol, 1.0mL (1MinCH 2 Cl 2 )). After stirring the reaction at room temperature in an air atmosphere for 0.5 hours, the reaction was quenched by adding 2 mL of saturated sodium thiosulfate solution, extracted with dichloromethane (5 mL×3), and then the organic phase was washed with water and saturated brine in sequence, anhydrous sulfuric acid Sodium dry. Filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain 1-naphthaldehyde 2a (50 mg, 64%) as light yellow liquid. The characterization data of this compound are as follows: 1 HNMR (400MHz, CDCl 3 )δ:7.58-7.64(m,2H),7.67-7.72(m,1H),7.92(d,J=7.6Hz,1H),7.98-7.99(m,1H),8.10(d,J=8.0Hz ,1H),9.26(d,J=8.0Hz,1H),10.40(s,1H); 13 CNMR (100MHz, CDCl 3 )δ: 124.9, 127.0, 128.5, 129.1, 130.6, 131.4, 133.7, 135.3, 136.7, 193.6; MS: m / z157 (MH) + .

Embodiment 2

[0018] According to the method described in Example 1, 1a (0.5mmol, 80mg) and acetonitrile (2mL) were added to a 10mL round bottom flask, and then ICl (1mmol, 1.0mL (1MinCH 2 Cl 2 )). After stirring the reaction at room temperature in an air atmosphere for 0.5 hours, the reaction was quenched by adding 2 mL of saturated sodium thiosulfate solution, extracted with dichloromethane (5 mL×3), and then the organic phase was washed with water and saturated brine in sequence, anhydrous sulfuric acid Sodium dry. Filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain 1-naphthaldehyde 2a (6 mg, 8%) as light yellow liquid.

Embodiment 3

[0020] According to the method described in Example 1, 1a (0.5mmol, 80mg) and tetrahydrofuran (2mL) were added to a 10mL round bottom flask, and then ICl (1mmol, 1.0mL (1MinCH 2 Cl 2 )). After stirring the reaction at room temperature in an air atmosphere for 0.5 hours, the reaction was quenched by adding 2 mL of saturated sodium thiosulfate solution, extracted with dichloromethane (5 mL×3), and then the organic phase was washed with water and saturated brine in sequence, anhydrous sulfuric acid Sodium dry. Filtered, spin-dried, and separated on a silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain 1-naphthaldehyde 2a (5 mg, 7%) as a pale yellow liquid.

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Abstract

The invention discloses a synthesizing method of a fused-ring aryl substituted formaldehyde compound, and belongs to the technical field of synthesis technologies of aldehyde compounds. According to the technical scheme, the synthesizing method of the fused-ring aryl substituted formaldehyde compound particularly comprises the steps that a 1-phenyl-4-pentyne-2-alcohol compound or a 1-(naphthalene-1-base)-4-pentyne-2-alcohol compound is dissolved in solvent, accelerant is added, a reaction is conducted in an air atmosphere at 0-40 DEG C, and the fused-ring aryl substituted formaldehyde compound is obtained, wherein the solvent adopts tetrahydrofuran or acetonitrile or dichloromethane, and the accelerant adopts iodine monochloride. The synthesizing method starts from the raw materials which are simple and easy to prepared, and by means of a one-pot cascade reaction, a 1-naphthaldehyde compound or a 1-phenanthrenecarboxaldehyde compound is obtained directly, that is to say, fused-ring aryl and aldehyde groups are built simultaneously in the one-pot cascade reaction; operation is convenient, the condition is mild, atoms are high in economic efficiency, substrates are wide in application scope, and the synthesizing method of the fused-ring aryl substituted formaldehyde compound is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of synthesis of aldehyde compounds, and in particular relates to a synthesis method of fused-ring aryl-substituted formaldehyde compounds. Background technique [0002] 1-naphthaldehyde and 1-phenanthrene formaldehyde and their derivatives belong to fused-ring aryl-substituted formaldehyde compounds, which are important organic synthesis intermediates and are often used in the preparation of drugs, natural products and other functional compounds. It has important application value in fine chemical industry and other fields. Regarding the synthesis of 1-naphthaldehyde compounds, there are mainly three approaches reported in the literature. The first approach is to introduce formyl (aldehyde) regioselectively into the α-position of the naphthalene ring to synthesize 1-naphthaldehyde. The disadvantage of this method is that the regioselectivity is difficult to control, and the obtained is often different body...

Claims

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Application Information

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IPC IPC(8): C07C45/00C07C45/26C07C45/66C07C47/546C07C47/575C07C47/55
CPCC07C45/00C07C45/26C07C45/66C07C47/546C07C47/575C07C47/55
Inventor 范学森李彬张新迎沈娜娜郭胜海
Owner HENAN NORMAL UNIV
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