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Free radical reaction method of 1, 6-diene and alcohol in additive-free system

A free radical and diene technology, applied in the field of regioselective free radical cyclization reaction, can solve the problems of cyclization reaction that have not been described, and achieve a wide range of effects

Active Publication Date: 2020-06-05
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, to date, alcohols a-C(sp 3 The 1,n-diene radical cyclization reaction initiated by the direct oxidative functionalization of )-H bond has not been described.

Method used

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  • Free radical reaction method of 1, 6-diene and alcohol in additive-free system
  • Free radical reaction method of 1, 6-diene and alcohol in additive-free system
  • Free radical reaction method of 1, 6-diene and alcohol in additive-free system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] Add 1,6-diene compound (40.2 mg, 0.2 mmol) shown in formula 1a, alcohol (1.0 mL) shown in formula 2a, tert-butyl peroxybenzoate (TBPB, 93.2 mg, 2.4 eq), then the reactor was stirred and reacted in an air atmosphere at 80°C, and the reaction process was monitored by TLC until the raw materials disappeared (reaction time was 15 hours). After the reaction was completed, the reaction solution was extracted with ethyl acetate, and the organic phase was extracted with Dry over anhydrous sodium sulfate, filter and concentrate under reduced pressure to remove the solvent, and the residue is separated by column chromatography (elution solvent: ethyl acetate / n-hexane) to obtain the target product I-1 (94% yield, d.r.>20: 1); 1 HNMR (500MHz, CDCl 3)δ: 7.59 (d, J = 8.0Hz, 2H), 7.36 (t, J = 8.0Hz, 2H), 7.15 (t, J = 7.5 Hz, 1H), 3.78 (t, J = 8.5Hz, 1H) , 3.44(t, J=10.0Hz, 1H), 2.75-2.69(m, 1H), 2.00(d, J=15.0Hz, 1H), 1.73(d, J=15.0Hz, 1H), 1.33(s, 3H), 1.29(s, 3H), 1.2...

Embodiment 2

[0036] Oxidizing agent replaces tert-butyl peroxybenzoate with tert-butanol peroxide (TBHP), and the consumption of tert-butanol peroxide is 2eq (51.5mg), and all the other conditions are with embodiment 1, and the yield that obtains target product I-1 is 78%.

Embodiment 3

[0038] The oxidizing agent replaces tert-butyl peroxybenzoate with tert-butanol peroxide (TBHP), the consumption of tert-butanol peroxide is 2eq (51.5mg), and the reaction temperature is reduced to 50°C, and all the other conditions are the same as in Example 1 to obtain the target product The yield of I-1 was 8%.

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Abstract

The invention discloses a free radical reaction method of 1, 6-diene and alcohol in an additive-free system, and relates to a regioselective free radical cyclization reaction method of a 1, 6-diene compound and an alcohol compound in a catalyst-free and alkali-free system under mild conditions. The method comprises the following steps: adding a 1, 6-diene compound, an alcohol compound and an oxidizing agent into a Schlenk reaction flask, and carrying out a stirring reaction process at a certain temperature under an air atmosphere condition to obtain a cyclized product.

Description

technical field [0001] The application belongs to the field of organic synthesis, and specifically relates to a regioselective radical cyclization reaction method of 1,6-diene compounds and alcohol compounds under mild conditions without a catalyst and an alkali system. Background technique [0002] Due to the need for environmental protection and the emergence of the concept of green and sustainable chemistry, the development of clean organic preparation methods is imminent. Therefore, the strategy of "one substance with multiple uses" in organic synthetic chemistry has attracted widespread attention from chemists, because it can not only reduce production costs but also reduce chemical waste emissions. In this context, the “one-for-all” design of reactants, catalysts, and solvents is the most commonly used approach. In the "one-purpose" design of the solvent that has been developed, it is not only used as a reaction medium, but also as a reactant, accelerator or activator...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/267C07D207/27
CPCC07D207/267C07D207/27Y02P20/584
Inventor 秦福华魏文廷
Owner NINGBO UNIV
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