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Isochroman derivative and its preparation method

A compound and isopropyl technology, applied in the field of isochroman derivatives and their preparation, can solve the problems of inability to screen excellent drugs, no reports, limited types of isochroman derivatives, etc.

Inactive Publication Date: 2005-05-18
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Throughout the published compound structures, it is found that the types of isochroman derivatives are very limited, and no isochroman derivatives connected to alkoxymethylene or aryloxymethylene at the 3-position have been seen, and the known preparation methods There are also various deficiencies, which are far from meeting the needs of screening excellent drugs
[0003] The applicant is engaged in the synthesis, separation, and purification of the alkoxy derivative of safrole oxide, 2-alkoxy-piperonyl ethanol, and its pharmacological research and application in the process of growth and apoptosis of vascular endothelial cells On the basis of (Chinese invention patent application number: 02110136.1), we focused on the research of isochroman derivatives connected with alkoxymethylene or aryloxymethylene at the 3-position, and designed and synthesized a new class of heterocyclic compounds That is, 3,4-dihydro-1,1-disubstituted-3-alkoxy(aryloxy)methyl-6,7-methylenedioxy-1H-benzo[c]pyran, regarding the The chroman derivative and its preparation method have not been reported at home and abroad at present

Method used

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  • Isochroman derivative and its preparation method
  • Isochroman derivative and its preparation method
  • Isochroman derivative and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Preparation of 3,4-dihydro-1,1-dimethyl-3-methoxymethyl-6,7-methylenedioxy-1H-benzo[c]pyran

[0026] 2.12 grams (0.010 moles) of 2-methoxyl-piperonyl ethanol was added to 25 milliliters of absolute methanol, then 20 milliliters of acetone was added, then 0.2 gram of p-toluenesulfonic acid was added, and after reflux reaction for 24 hours, the The methanol and acetone were distilled off under pressure, the remaining mixture was cooled to 25°C, 30 ml of water was added, extracted three times with ethyl acetate (100 ml each time), dried with anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and the residue was washed with silica gel Column chromatography separation (developing solvent is petroleum ether / ethyl acetate=3:1, volume ratio) to obtain 3,4-dihydro-1,1-dimethyl-3-methoxymethyl-6,7- Methylenedioxy-1H-benzo[c]pyran (1.5 g), 60% yield.

[0027] The structural formula is as follows:

[0028]

[0029] Molecular formula: C 14 h...

Embodiment 2

[0037] Example 2: Preparation of 3,4-dihydro-1,1-dimethyl-3-isopropoxymethyl-6,7-methylenedioxy-1H-benzo[c]pyran

[0038] 2.36 grams (0.010 moles) of 2-isopropoxy-piperonyl ethanol was added to 25 milliliters of anhydrous methanol, then 20 milliliters of acetone was added, then 0.2 gram of p-toluenesulfonic acid was added, and after heating to reflux for 24 hours, Distill methanol and acetone under reduced pressure, cool the remaining mixture to 25°C, add 30 ml of water, extract three times with ethyl acetate (100 ml each time), dry with anhydrous magnesium sulfate, filter, concentrate under reduced pressure, and use Separation by silica gel column chromatography (developing solvent is petroleum ether / ethyl acetate=3:1, volume ratio) to obtain 3,4-dihydro-1,1-dimethyl-3-isopropoxymethyl-6, 7-Methylenedioxy-1H-benzo[c]pyran (1.8 g), 61% yield.

[0039] The structural formula is as follows:

[0040]

[0041] Molecular formula: C 16 h 22 o 4 .

[0042] Molecular weight: ...

Embodiment 3

[0048] Example 3: Preparation of 3,4-dihydro-1,1-dimethyl-3-phenoxymethyl-6,7-methylenedioxy-1H-benzo[c]pyran

[0049] 2.72 grams (0.010 moles) of 2-phenoxy-piperonyl ethanol was added to 25 milliliters of absolute methanol, then 20 milliliters of acetone was added, then 0.2 gram of p-toluenesulfonic acid was added, and after reflux reaction for 14 hours, the The methanol and acetone were distilled off under pressure, the remaining mixture was cooled to 20°C, 30 ml of water was added, extracted three times with ethyl acetate (100 ml each time), dried with anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and the residue was washed with silica gel Column chromatography separation (developing solvent is petroleum ether / ethyl acetate=9:1, volume ratio) to obtain 3,4-dihydro-1,1-dimethyl-3-phenoxymethyl-6,7- Methylenedioxy-1H-benzo[c]pyran (1.9 g), 60% yield.

[0050] The structural formula is as follows:

[0051]

[0052] Molecular formula: C 19 h ...

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Abstract

The present invention relates to isochroman derivatives 3,4-dihydro-1,1-disubstituted-3-alkoxy (aryloxy)methyl-6,7-methylenedioxy-1H of general formula (I) - Benzo[c]pyran. where R stands for C 1-6 Alkyl, phenyl, substituted phenyl; R 1 stands for H, C 1-5 Alkyl, phenyl, substituted phenyl; R 2 stands for C 1-5 Alkyl, phenyl, substituted phenyl; R 1 R 2 Represents cyclopentyl, substituted cyclopentyl, cyclohexyl, substituted cyclohexyl. The present invention also relates to the preparation method of the compound, that is, reflux reaction of 2-alkoxy-piperonyl ethanol and aldehyde or ketone compound in the presence of an acid catalyst, decompression, cooling, extraction, filtration, concentration under reduced pressure, and the concentrate Use silica gel column chromatography to obtain the product.

Description

(1) Technical field [0001] The present invention relates to isochroman derivatives and preparation methods thereof, in particular to 3,4-dihydro-1,1-disubstituted-3-alkoxy (aryloxy)methyl-6,7-methylenedioxy- 1H-benzo[c]pyran and its synthesis, separation and purification methods. (2) Background technology [0002] In natural products, although compounds containing isochroman structural units have not been isolated in large numbers, people have become very interested in this type of structure, because the biological activity tests of such derivatives that have been synthesized show that such derivatives have anti-inflammatory properties. Antibacterial and other pharmacological activities. Such as the isochromanone structure involved in the patent No. US6348603, JP2001139570, US6075152, and US6002020; there are also some patents involving 1-substituted and 4-substituted isochroman structures. The preparation methods of such derivatives include: 1) the reaction of substituted...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04
Inventor 赵宝祥
Owner SHANDONG UNIV