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Diparacyclic acetal compounds and their preparation methods and applications

A technology of compounds and cyclic acetals, which is applied in the direction of silicon organic compounds, chemical instruments and methods, compounds of group 4/14 elements of the periodic table, etc., can solve the problem of di-paracyclic acetal compounds that cannot undergo multiple substitution reactions Due to problems such as structural limitations, the reaction process is safe and controllable, the possibility of becoming a drug is improved, and the forward reaction rate is high.

Active Publication Date: 2021-01-01
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a kind of bis-paracyclic acetal compound, aiming to solve the problem that the bis-paracyclic acetal compound prepared in the prior art is limited in structure and cannot perform multiple substitution reactions

Method used

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  • Diparacyclic acetal compounds and their preparation methods and applications
  • Diparacyclic acetal compounds and their preparation methods and applications
  • Diparacyclic acetal compounds and their preparation methods and applications

Examples

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preparation example Construction

[0062] Correspondingly, the embodiment of the present invention also provides a preparation method of bis-cyclic acetal compounds. The method comprises the steps of:

[0063] S01. provide nucleophile compound, the general structural formula of the nucleophile compound is

[0064] S02. Provide allyl alcohol compounds, the general structural formula of the allyl alcohol compounds is

[0065] S03. Mixing the nucleophile compound, the allyl alcohol compound, the acridinium photocatalyst and the hydrogen transfer reagent, adding a solvent to dissolve to obtain a reaction solution;

[0066] S04. Carrying out the cyclization reaction of the reaction solution under the irradiation of visible light to obtain the bis-cycloacetal compound;

[0067] The general structural formula of the bis-cyclic acetal compound is where the R 1 , R 2 , R 3 each independently selected from C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylox...

Embodiment 1

[0090] This example provides 3-(4-methoxybenzyl)2,3,4,5-tetrahydrofuro[2,3-b]furan and its preparation method. The structural formula of the 3-(4-methoxybenzyl) 2,3,4,5-tetrahydrofuro[2,3-b]furan is shown in the following molecular structural formula I1:

[0091]

[0092] Its preparation steps are as follows: In a dry 8mL test tube, add a photocatalyst (0.01mmol, 0.05eq), diphenyl disulfide (0.04mmol, 0.2eq), 4-methyl Oxycinnamyl alcohol (0.2mmol, 1eq) and 3.0mL of anhydrous 1,2-dichloroethane, replaced by argon three times, after the reaction test tube was sealed, 2,3-dihydrofuran (0.8mmol, 4eq) was slowly added to the reaction The system was stirred for 18 hours at room temperature under blue light irradiation. After the reaction was completed, the reaction solution was spin-dried and separated by column chromatography to obtain the target product, a colorless oily liquid, with a yield of 60% and a dr value of 1.9:1. Correlation characterization analysis, the result is:...

Embodiment 2

[0094] This example provides a kind of 3-benzyl-2,3,4,5-tetrahydrofuro[2,3-b]pyran and its preparation method. The structural formula of the 3-benzyl-2,3,4,5-tetrahydrofuro[2,3-b]pyran is shown in the following molecular structural formula I2:

[0095]

[0096] Its preparation steps are as follows: in a dry 8mL test tube, add a photocatalyst (0.01mmol, 0.05eq), diphenyl disulfide (0.04mmol, 0.2eq), trans-cinnamon Alcohol (0.2mmol, 1eq) and 3.0mL of anhydrous 1,2-dichloroethane, replaced by argon three times, after the reaction test tube was sealed, 3,4-dihydro-2H-pyran (0.8mmol, 4eq) was added slowly The reaction system was stirred for 18 hours at room temperature under blue light irradiation. After the reaction was completed, the reaction solution was spin-dried and separated by column chromatography to obtain the target product, a colorless oily liquid, with a yield of 81% and a dr value of 1.8:1. Correlation characterization analysis, the result is: Cis-syn: 1 H NMR (...

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Abstract

The invention provides a double-ring-fused aldehyde compound as well as a preparation method and application thereof. The molecular structure formula of the double-ring-fused aldehyde compound is shown in formula (I) in the description. The double-ring-fused aldehyde compound comprises four double-ring-fused structures: 5 / 5, 5 / 6, 5 / 7 and 6 / 6; the structure can be adjusted and modified, so that thestability of the ring-fused aldehyde compound in an acidic condition is improved; the probability of preparing into a medicine can be improved.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, in particular to a bis-paracyclic acetal compound and its preparation method and application. Background technique [0002] The biscyclic acetal structure is a very important structure in natural products and drug molecules. This type of structure not only has a relatively rigid skeleton structure and small molecular weight, but also the oxygen atoms in the structure can serve as endogenous hydrogen bond acceptors, which can bind to specific enzymes through hydrogen bond interactions. In addition, compared with ordinary acetal compounds, the double ring acetal structure has a certain stability under acidic conditions, so that it can exist stably under gastric acid conditions in the body, thus having the potential of being a drug. [0003] Biscyclic acetal compounds have a unique 3D structure and are an important building block for pharmaceutical intermediates and natural produ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04C07F7/08
CPCC07D493/04C07F7/0838C07F7/0872
Inventor 黄湧陈杰安武丰瑾
Owner PEKING UNIV SHENZHEN GRADUATE SCHOOL
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