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4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-3,4-diol benzyl ether and synthesis method thereof

A technology of oxabicyclo and diol benzyl ether, which is applied in the field of fine chemical synthesis, can solve the problems of high application concentration, high water solubility, and easy loss, and achieve high drug efficacy, low dosage, and large dosage Effect

Active Publication Date: 2017-09-22
GUANGXI UNIV FOR NATITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] (3R,4R)-4,7,7-Trimethyl-6-oxabicyclo[3.2.1]octane-3,4-diol belongs to monoterpene oxabicyclols, which can be synthesized from α-pinene and its oxygen-containing derivatives through multi-step chemical synthesis or one-step catalytic synthesis [Zhuang Daozhan et al., Forestry Chemistry and Industry, 2015, 35(1))]; its molecular structure has 6-oxabicyclic [3.2.1 ]octane skeleton and 2 chemically active hydroxyl functional groups, easily soluble in water, (3R,4R)-4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-3, 4-diol itself and its acetate derivatives have certain herbicidal activity on ryegrass, rapeseed and barnyard grass, but its water solubility is large and the application concentration is high. Insufficient high

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  • 4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-3,4-diol benzyl ether and synthesis method thereof
  • 4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-3,4-diol benzyl ether and synthesis method thereof
  • 4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-3,4-diol benzyl ether and synthesis method thereof

Examples

Experimental program
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Embodiment 1

[0023] A kind of 4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-3,4-diol benzyl ether with herbicidal activity, the synthetic method of this benzyl ether compound comprises the following steps :

[0024] (1) Add 4.65g (25mmol) of compound I, 3.16g (25mmol) of m-methylbenzyl chloride, 125mL of tetrahydrofuran and 3.6g (150 mmol) of sodium hydride into the reactor. The ratio of the amount of benzyl to sodium hydride is 1:1:6, and the reaction is heated under reflux for 7 hours, wherein the compound I is (3R,4R)-4,7,7-trimethyl-6-oxabicyclo[ 3,2,1] octane-3,4-diol, THF is the solvent;

[0025] (2) After the reaction is over, cool the reaction liquid, and then evaporate the solvent under reduced pressure to recover the solvent. Dissolve the residue in 200 mL of anhydrous ether, transfer it to a 1-liter separatory funnel, and then add 200 mL of ice water to dissolve and remove sodium chloride and untreated Reaction of sodium hydride; liquid separation, recovery of the organic phase, t...

Embodiment 2

[0028] A kind of 4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-3,4-diol benzyl ether with herbicidal activity, the synthetic method of this benzyl ether compound comprises the following steps :

[0029] (1) Add 9.3g (50mmol) of compound I, 17.6g (125mmol) of m-methylbenzyl chloride, 250mL of tetrahydrofuran and 7.2g (300 mmol) of sodium hydride into the reactor, heat and reflux for 5 hours, wherein compound I is (3R,4R)-4,7,7-trimethyl-6-oxabicyclo[3,2,1]octane-3,4-diol, THF is the solvent;

[0030] (2) After the reaction is over, cool the reaction liquid, and then evaporate the solvent under reduced pressure to recover the solvent. Dissolve the residue in 200 mL of anhydrous ether, transfer it to a 1-liter separatory funnel, and then add 200 mL of ice water to dissolve and remove sodium chloride and untreated Reaction of sodium hydride; liquid separation, recovery of the organic phase, the water phase was extracted twice with 200mL ether; the organic phase was combined, evaporat...

Embodiment 3

[0033]A kind of 4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-3,4-diol benzyl ether with herbicidal activity, the synthetic method of this benzyl ether compound comprises the following steps :

[0034] (1) Add 4.65g (25mmol) of compound I, 3.16g (25mmol) of p-methylbenzyl chloride, 125mL of tetrahydrofuran and 3.6g (150 mmol) of sodium hydride into the reactor. The ratio of the amount of benzyl to sodium hydride is 1:1:6, and the reaction is heated under reflux for 7 hours, wherein the compound I is (3R,4R)-4,7,7-trimethyl-6-oxabicyclo[ 3,2,1] octane-3,4-diol, THF is the solvent;

[0035] (2) After the reaction is over, cool the reaction liquid, and then evaporate the solvent under reduced pressure to recover the solvent. Dissolve the residue in 200 mL of anhydrous ether, transfer it to a 1-liter separatory funnel, and then add 200 mL of ice water to dissolve and remove sodium chloride and untreated Reactive sodium hydride; liquid separation, reclaiming the organic phase, and ex...

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Abstract

The invention belongs to the technical field of synthesis of fine chemicals, and particularly relates to 4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-3,4-diol benzyl ether and a synthesis method of the 4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-3,4-diol benzyl ether. The synthesis method comprises the following steps: taking tetrahydrofuran as a solvent, and conducting an etherification reaction on (3R,4R)-4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-3,4-diol and benzyl halides under the action of sodium hydride to synthesize the 4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-3,4-diol benzyl ether. The benzyl ether compound is excellent in herbicidal activity, can inhibit the growth of monocotyledon and dicotyledon like barnyard grass, oilseed rape, ryegrass and abutilon theophrasti, and has an excellent application prospect in the aspect of preparation of herbicides.

Description

technical field [0001] The invention belongs to the technical field of synthesis of fine chemicals, in particular to a 4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-3,4-diol benzyl ether with herbicidal activity and its synthesis method. Background technique [0002] (3R,4R)-4,7,7-Trimethyl-6-oxabicyclo[3.2.1]octane-3,4-diol belongs to monoterpene oxabicyclols, which can be synthesized from α-pinene and its oxygen-containing derivatives through multi-step chemical synthesis or one-step catalytic synthesis [Zhuang Daozhan et al., Forestry Chemistry and Industry, 2015, 35(1))]; its molecular structure has 6-oxabicyclic [3.2.1 ]octane skeleton and 2 chemically active hydroxyl functional groups, easily soluble in water, (3R,4R)-4,7,7-trimethyl-6-oxabicyclo[3.2.1]octane-3, 4-diol itself and its acetate derivatives have certain herbicidal activity on ryegrass, rapeseed and barnyard grass, but its water solubility is large and the application concentration is high. Not high enough. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/00A01N43/12A01P13/00
Inventor 黄道战蓝虹云余会成卢建芳
Owner GUANGXI UNIV FOR NATITIES