A kind of 2,6-dioxabicyclo[3.3.2]octane derivative and its synthesis method

A technology of dioxobicyclone and synthesis method, which is applied in 2 fields and can solve problems such as difficulty in synthesis

Active Publication Date: 2021-05-04
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, 2,6-dioxabicyclo[3.3.1]octane compounds have been efficiently synthesized, but the new 2,6-dioxabicyclo[3.3.2]octane skeleton has not been realized, and the synthesis of this There are also certain difficulties and challenges

Method used

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  • A kind of 2,6-dioxabicyclo[3.3.2]octane derivative and its synthesis method
  • A kind of 2,6-dioxabicyclo[3.3.2]octane derivative and its synthesis method
  • A kind of 2,6-dioxabicyclo[3.3.2]octane derivative and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of 2,6-dioxabicyclo[3.3.2]octane derivatives as shown in structural formula 3a

[0032] Add the compound (0.2mmol) as shown in structural formula 1a, Selectflour (0.16mmol) and cuprous chloride (0.04mmol) into a Kjeldahl flask with a magnet, and add 2.0mL of ethyl acetate after vacuumizing and filling with nitrogen, Then put the reaction system in an oil bath at 40°C for 12 hours, and monitor it with a TLC board. After the reaction is complete, remove the solvent under reduced pressure, and separate by column chromatography (petroleum ether: ethyl acetate = 35: 1), that is, the structural formula 2,6-dioxabicyclo[3.3.2]octane derivative shown in 3a (white solid, 42mg, 85%); the chemical reaction formula of this method is:

[0033]

[0034] The 2,6-dioxabicyclo[3.3.2]octane derivative shown in structural formula 3a was detected by nuclear magnetic resonance, melting point, infrared and high-resolution mass spectrometry, and the detection data were as follows...

Embodiment 2

[0040] Synthesis of 2,6-dioxabicyclo[3.3.2]octane derivatives as shown in structural formula 3b

[0041] Add the compound (0.2mmol) as shown in structural formula 1b, Selectflour (0.16mmol) and cuprous chloride (0.04mmol) into a Kjeldahl flask with a magnet, and add 2.0mL of ethyl acetate after vacuumizing and filling with nitrogen, Then put the reaction system in an oil bath at 40°C for 12 hours, and monitor it with a TLC board. After the reaction is complete, remove the solvent under reduced pressure, and separate by column chromatography (petroleum ether: ethyl acetate = 35: 1), that is, the structural formula 2,6-dioxabicyclo[3.3.2]octane derivative shown in 3b (white solid, 40mg, 72%); the chemical reaction formula of this method is:

[0042]

[0043] The 2,6-dioxabicyclo[3.3.2]octane derivative shown in structural formula 3b was detected by nuclear magnetic resonance, melting point, infrared and high-resolution mass spectrometry, and the detection data were as follows...

Embodiment 3

[0049] Synthesis of 2,6-dioxabicyclo[3.3.2]octane derivatives as shown in structural formula 3c

[0050] Add the compound (0.2mmol) as shown in structural formula 1c, Selectflour (0.16mmol) and cuprous chloride (0.04mmol) into a Kjeldahl flask with a magnet, and add 2.0mL ethyl acetate after vacuumizing and filling with nitrogen, Then put the reaction system in an oil bath at 40°C for 12 hours, and monitor it with a TLC board. After the reaction is complete, remove the solvent under reduced pressure, and separate by column chromatography (petroleum ether: ethyl acetate = 35: 1), that is, the structural formula 2,6-dioxabicyclo[3.3.2]octane derivative shown in 3c (white solid, 45mg, 69%); the chemical reaction formula of this method is:

[0051]

[0052] The 2,6-dioxabicyclo[3.3.2]octane derivative shown in structural formula 3c was detected by nuclear magnetic resonance, melting point, infrared and high-resolution mass spectrometry, and the detection data were as follows: ...

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Abstract

The invention discloses a 2,6-dioxobicyclo[3.3.2]octane derivative and a synthesis method thereof. The synthesis method of the derivative is based on (E)-2-hydroxyl-1-naphthalene vinyl derivative The substrate is under the action of 1-chloromethyl-4-fluoro-1, 4-diazotized bicyclo[2.2.2]octane bis(tetrafluoroborate) salt and cuprous chloride, and the reaction obtains a novel 2,6-Dioxobicyclo[3.3.2]octane skeleton derivative compound. The method of the invention is simple to operate, and the reaction conditions are mild, and a novel 3D skeleton, two rings, three new chemical bonds (two C-O, one C-C) and four chiral centers are constructed in a one-pot reaction And a single stereo configuration was obtained, and a series of 2,6-dioxobicyclo[3.3.2]octane derivatives were constructed.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and specifically relates to a 2,6-dioxobicyclo[3.3.2]octane derivative and a synthesis method thereof. Background technique [0002] The bridged cyclooctyl ether skeleton structure widely exists in natural products and drug molecules. Many compounds containing bridged cyclooctyl ether structures have good biological and pharmaceutical activities, including antibacterial, antiviral, antitumor and so on. At the same time, bridged ring compounds with complex structures have always attracted the attention of chemists, and a series of new strategies for constructing bridged ring ether skeletons have been developed and applied. So far, 2,6-dioxabicyclo[3.3.1]octane compounds have been efficiently synthesized, but the new 2,6-dioxabicyclo[3.3.2]octane skeleton has not been realized, and the synthesis of this There are also certain difficulties and challenges. From the perspective of biomed...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/08
CPCC07D493/08
Inventor 周岭杨慧陈洁
Owner NORTHWEST UNIV
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