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Solid phase synthesizing method of dihydronaphthalene compound

A solid-phase synthesis and compound technology, applied in the field of organic chemistry, can solve problems such as low yield, and achieve the effects of good product yield, simple operation and simple post-processing

Inactive Publication Date: 2016-05-04
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the invention is to solve the problem of low yield in the solid-phase synthesis method of existing dihydronaphthalene compounds, and provide a new solid-phase synthesis method of dihydronaphthalene compounds

Method used

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  • Solid phase synthesizing method of dihydronaphthalene compound
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  • Solid phase synthesizing method of dihydronaphthalene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 Under the protection of nitrogen, 1% cross-linked polystyrene supported selenium bromide II (Br%=0.99mmol / g, 2.5g, 2.48mmol), tetrahydrofuran (24mL) and N,N-dimethylform The amide (6mL) was placed in a reaction flask and allowed to stand at room temperature for 4h. After the resin was swollen, sodium borohydride (189.2mg, 5.0mmol) was added, and the reaction was stirred at 40°C for 8h. Allyl bromide (0.665g, 5.5mmol) was added dropwise, and the reaction was continued to stir at 40°C for 12h. After the reaction is completed, filter with a sand core funnel, and then use dichloromethane (3×10mL), water (3×10mL), water+tetrahydrofuran (V / V=1:1, 3×10mL), tetrahydrofuran (3×10mL) , ethanol (3×10mL), methanol (3×10mL), ether (3×10mL), dichloromethane (10mL), acetone (3×10mL) to wash the resin, and dry to obtain polystyrene-loaded allyl selenide III (2.36 g, 98.2%).

[0033] IR(KBr): υ max =3068, 3019, 2847, 1565, 1415, 1185, 1016, 907, 751cm –1 .

Embodiment 2

[0034] Example 2 Under the protection of nitrogen, 1% cross-linked polystyrene supported selenium bromide II (Br% = 0.99mmol / g, 2.5g, 2.48mmol), tetrahydrofuran (80mL) and N, N-dimethyl form The amide (20 mL) was placed in a reaction flask and allowed to stand at room temperature for 4 h. After the resin was swollen, sodium borohydride (0.473g, 12.5mmol) was added, stirred at 40°C for 2h, allyl bromide (1.572g, 13.0mmol) was added dropwise, and stirred at 40°C for 5h. After the reaction is completed, filter with a sand core funnel, and then use dichloromethane (5×10mL), water (3×10mL), water+tetrahydrofuran (V / V=1:1, 3×10mL), tetrahydrofuran (3×10mL) , ethanol (3×10mL), methanol (3×10mL), ether (3×10mL), dichloromethane (10mL), acetone (3×10mL) to wash the resin, and dry to obtain polystyrene-loaded allyl selenide III (2.35 g, 98.0%), IR is consistent with Example 1.

Embodiment 3

[0035] Example 3 Under the protection of nitrogen, 1% cross-linked polystyrene supported selenium bromide II (Br%=0.99mmol / g, 2.5g, 2.48mmol), tetrahydrofuran (80mL) and N,N-dimethylform The amide (20 mL) was placed in a reaction flask and allowed to stand at room temperature for 4 h. After the resin was swollen, sodium borohydride (0.946g, 25.0mmol) was added, stirred at 40°C for 12h, allyl bromide (3.08g, 25.5mmol) was added dropwise, and stirred at 40°C for 24h. After the reaction is completed, filter with a sand core funnel, and then use dichloromethane (5×10mL), water (3×10mL), water+tetrahydrofuran (V / V=1:1, 3×10mL), tetrahydrofuran (3×10mL) , ethanol (3×10mL), methanol (3×10mL), ether (3×10mL), dichloromethane (10mL), acetone (3×10mL) to wash the resin, and dry to obtain polystyrene-loaded allyl selenide III (2.35 g, 98.0%), IR is consistent with Example 1.

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Abstract

A solid phase synthesizing method of a dihydronaphthalene compound I belongs to the field of organic chemistry and comprises: 1, using 1% crosslinked polystyrene resin as a carrier to prepare a polystyrene-loaded selenium base succinimide reagent III; 2, under catalyzing of fluoroform sulfonic acid trimethyl estersil, using the III to induce olefin V to be subjected to intramolecular cyclization to form 3-polystyrene-loaded selenium base-1,2,3,4-tetrahydronaphthalene VI; 3, removing VI by an oxidant through oxidation without further separating, thereby directly obtaining dihydronaphthalene I. Raw materials are easy to obtain, the product yield is good, the purity is high, the operation is simple and convenient, the posttreatment is simple and the method has well industrial application prospect.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and specifically relates to a solid-phase synthesis method of a dihydronaphthalene compound I of the following structure: [0002] [0003] where R 1 =H, -CN, -COOCH 3 ; 2 = H, C 1－4 Alkyl, -COOCH 3 ; 3 =H, -CH 3 , Ph, -C 6 h 4 CH 3 ,-C 6 h 4 OCH 3 ,-C 6 h 4 Cl, -C 6 h 4 Br; R 4 = H, C 1－6 Alkyl, Ph, -C 6 h 4 CH 3 ,-C 6 h 4 OCH 3 ,-C 6 h 4 Cl, -C 6 h 4 COOCH 3 ,-C 6 h 4 NO 2 ; 5 =H, -OCH 3 , -OBn; R 6 =H, -OCH 3 ,-Br. Background technique [0004] Since Naproxen, the first product of naphthalene-based drugs developed by Syntex Corporation of the United States in the early 1960s, has exhibited various pharmacological activities such as high efficiency and low toxicity, long-acting antipyretic, analgesic, anti-inflammatory, etc. Widely used all over the world. Studies have shown that most compounds containing hydronaphthalene ring structural units have pharm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/47C07C1/32C07C13/48C07C67/317C07C69/753C07C69/757C07C17/35C07C25/22C07C41/18C07C43/21C07C69/76
CPCC07C1/321C07C17/35C07C41/18C07C67/317C07C253/30C07C255/47C07C13/48C07C69/753C07C69/757C07C25/22C07C43/21C07C69/76
Inventor 汤峨张梦高占勇
Owner YUNNAN UNIV