(1R-cis)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane carboxylic acid

White Solid

Cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid is an organobromine compound consisting of cyclopropanecarboxylic acid having a 2,2-dibromovinyl group at the 3-position and two methyl groups at the 2-position. It is an organobromine compound and a monocarboxylic acid. It derives from a cyclopropanecarboxylic acid.

The preparation method can be prepared by using the first chrysanthemic acid or cis-permethric acid as raw materials. (±) Trans-chrysanthemic acid synthesized by Martel method, via L-(+)-threo-type p-nitrophenyl-2-N, N-dimethyl-1, 3-propanediol or α-methylbenzylamine Separation yields (+) trans-chrysanthemic acid and (-) trans-chrysanthemic acid. (+) Trans-chrysanthemum acid is 1R, 3R-chrysanthemum acid, esterified by methanol to obtain dextran-trans-chrysanthemum methyl ester, further ozonation reaction, the temperature is maintained at -10 ~ 12 ℃, get dextran-trans-carboxaldehyde Methyl acid ester, which is then epimerized, reacted in a sodium methoxide methanol solution, the temperature is below 10°C, charged under nitrogen protection, and then gradually heated to methanol reflux, the reaction is completed after 3h, demethanol, after After treatment, acetal lactone is obtained, which is treated with dioxane and water and a small amount of acetic acid, and then recrystallized into hemiacetal lactone. The lactone is ring-opened to obtain 1R, 3S-capronic acid, and then The Wittig reaction of triphenylmethylenephosphonium dibromide produces 1R, 3R-dibromethrin. (-) Trans-chrysanthemum acid, ie 1S, 3S-chrysanthemum acid, generates 2, 2-dimethyl(2′-hydroxy-2′-methylpropanyl)cyclopropanecarboxylic acid in acid solution, in tert-butanol In the presence of potassium, carry out C1 epimerization to obtain bicyclic lactone, and then carry out acid hydrolysis to obtain 1R, 3S-chrysanthemum acid, and then ozonation to obtain 1R, 3S-glucuronic acid, which is also the same as triphenylmethylene Phosphorus dibromide reaction yields 1R, 3R-dibromethrin. It is also possible to use 1R, 3S-carboxuronic acid and tribromomethane to obtain a tribromobicyclic lactone compound, and then use zinc powder in tetrahydrofuran to eliminate the reaction to obtain 1R, 3R-dibromethic acid. It is also possible to use 1R, 3R-permethric acid to react with AlBr3 to obtain 1R, 3R-dibromethic acid. Using cis-permethrin as raw material to prepare 1R, 3R-dibromo-chrysanthemic acid is to resolve (±) cis-permethrin to obtain (+) cis-permethrin, which is subjected to ozonation and Wittig reaction , Can also get 1R, 3R-dibromethrin.

A pesticide transformation product.

Molecular Weight:297.97
XLogP3:3.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:297.90271
Monoisotopic Mass:295.90475
Topological Polar Surface Area:37.3
Heavy Atom Count:12
Complexity:241
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes