142004-23-7

Usage

Explanation

The molecular formula represents the number of atoms of each element present in a molecule of the compound.

Explanation

The compound is derived from 1,3-dioxolane-4-methanol by the addition of a bromomethyl group.

Explanation

The stereochemistry of the compound is important for its biological activity and interactions with other molecules. The (2R,4R)configuration indicates the spatial arrangement of the atoms in the molecule.

Explanation

These functional groups are present in the compound and contribute to its chemical properties and reactivity.

Explanation

The compound is commonly used in the synthesis of various pharmaceuticals and agrochemicals due to its unique chemical properties and reactivity.

Explanation

The compound's potential applications in drug development and other chemical processes make it a subject of interest for researchers and chemists.

Explanation

The solubility of the compound is not provided in the material, but it would depend on the solvent used.

Explanation

The boiling point of the compound is not provided in the material, but it is an important physical property that can affect its handling and use.

Explanation

The melting point of the compound is not provided in the material, but it is an important physical property that can affect its stability and handling.

Explanation

The density of the compound is not provided in the material, but it is a physical property that can affect its handling and use in various applications.

Bromomethylated derivative

1,3-dioxolane-4-methanol

Stereochemistry

(2R,4R)-

Functional groups

Bromomethyl, 2,4-dichlorophenyl, acetate

Applications

Pharmaceutical and agrochemical synthesis

Interest to researchers and chemists

Drug development and chemical processes

Solubility

Unknown (depends on the solvent)

Boiling point

Unknown

Melting point

Unknown

Density

Unknown

Upstream product

• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 
• 2631-72-3 2,4-dichlorophenacyl bromide 
• 3396-11-0 cesium acetate 
• 82966-35-6 (2R,4R)-cis-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-<<<(4-methylphenyl)sulfonyl>oxy>methyl>-1,3-dioxolane 

Relevant academic research and scientific papers

Lipase-catalyzed resolution of 1,3-dioxolane derivatives: Synthesis of a homochiral intermediate for antifungal agents

Dioxolane alcohol (±)-1 and the corresponding acid (±)-2 were kinetically resolved into their respective enantiomers by lipase-catalyzed hydrolysis and esterification reactions. Various alcohols were tested to resolve the acid (±)-2, and the desired (2R,4R)-isomer of the acid was obtained with >96% ee as the best result. Halogenated solvents such as methylene chloride and 1,2-dichloroethane were found to raise the reactivity and selectivity of the system. After recrystallization, the purity of the desired (2R,4R)-acid could be increased to over 98% ee.

Stereoisomers of ketoconazole: Preparation and biological activity

The four stereoisomers of the antifungal agent ketoconazole (1) were prepared and evaluated for their selectivity in inhibiting a number of cytochrome P-450 enzymes. Large differences in selectivity among the isomers were observed for inhibition of the cytochromes P-450 involved in steroid biosynthesis, whereas little differences was observed for inhibition of those associated with hepatic drug metabolism. The cis-(2S,4R) isomer 2 was the most effective against rat lanosterol 14α-demethylase, (2S,4R)-2 > (2R,4S)-4 >> (2R,4R)-3 = (2S,4S)-5, and progesterone 17α,20-lyase, (2S,4R)-2 >> (2S,4S)-5 > (2R,4R)-3 = (2R,4S)-4, whereas the cis-(2R,4S) isomer 4 was more effective against cholesterol 7α-hydroxylase, (2R,4S)-4 > (2S,4S)-5 > (2R,4R)-3 > (2S,4R)-2, and the trans-(2S,4S) isomer 5 was the most effective against aromatase, (2S,4R)-5 >> (2R,4R)-3 = (2R,4S)-4 > (2S,4R)-2. The cis- (2S,4R) and trans-(2R,4R) isomers 2 and 3 are equipotent in inhibiting corticoid 11β-hydroxylase and much more effective than their antipodes. Little selectivity was observed for inhibition of cholesterol side chain cleavage or xenobiotic hydroxylases. These data indicate that the affinity of azoles for cytochrome P-450 enzymes involved in steroid synthesis is highly dependent on the stereochemistry of the entire molecule, whereas binding to drug metabolizing enzymes is a less selective process.