1653-64-1

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Methylenedioxyphenethylamine hydrochloride is used as a key intermediate for the synthesis of bifendate derivatives, which serve as anticancer agents through P-glycoprotein (Pgp) inhibition. This application is crucial in the development of treatments for cancer, as Pgp inhibition can help overcome multidrug resistance in cancer cells.
Used in Chemical Synthesis:
3,4-Methylenedioxyphenethylamine hydrochloride is also used as a starting material for the synthesis of N-(3,4-methylenedioxyphenethyl)-2-(3-bromo-4-methoxyphenyl)acetamide, a compound with potential applications in various fields, including pharmaceuticals and materials science. Its versatility as a synthetic building block makes it valuable for creating new molecules with specific properties and functions.

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 3299, 1950 DOI: 10.1021/ja01163a529

InChI:InChI=1S/C9H11NO2.ClH/c10-4-3-7-1-2-8-9(5-7)12-6-11-8;/h1-2,5H,3-4,6,10H2;1H

Upstream product

• 87212-43-9 (2-Benzo[1,3]dioxol-5-yl-ethyl)-phosphoramidic acid diisopropyl ester 
• 7647-01-0 hydrogenchloride 
• 497-25-6 dimethylenecyclourethane 
• 120-57-0 piperonal 
• 1485-00-3 5-(2-nitrovinyl)benzo[1,3]dioxole 

Downstream Products

• 6006-82-2 3,4-methylenedioxyphenethyl alcohol 
• 180798-12-3 N-(2-benzo[1,3]dioxol-5-yl-ethyl)-2-(4-bromophenyl)acetamide 
• 1417558-45-2 C₂₃H₁₉N₃O₂ 
• 30044-78-1 pseudocoptisine chloride 
• 25829-00-9 N-(2-(benzo[d] [1,3]dioxol-5-yl)ethyl)-2-(2-bromo-4,5-dimethoxyphenyl)acetamide 
• 1029806-33-4 5-(4-bromobenzyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline oxalate 
• 1029806-35-6 5-[4-(4-chloropyridin-3-yl)benzyl]-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester 
• 1029806-37-8 5-[4-(4-methoxypyridin-3-yl)benzyl]-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester 
• 1029806-34-5 5-(4-bromobenzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester 
• 1030137-90-6 5-[4-(4-chloropyridin-3-yl)benzyl]-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 1030137-91-7 5-[4-(4-methoxypyridin-3-yl)benzyl]-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 1029806-32-3 5-(4-bromobenzyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 180798-19-0 5-(4-bromobenzyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 1443828-04-3 5-((4-methoxyphenoxy)methyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 

Relevant academic research and scientific papers

Berberine derivatives, preparation method thereof and application of berberine derivatives as p300 HAT small molecule inhibitor

The invention discloses berberine derivatives, a preparation method thereof and an application of the berberine derivatives as a p300 HAT small molecule inhibitor, and belongs to the technical field of medicinal chemistry. An effective component berberine hydrochloride in a natural product coptis chinensis is taken as a research object and is subjected to structural modification and transformationso as to obtain a series of berberine hydrochloride derivatives. The berberine derivatives have the characteristics of high activity, high selectivity and high safety for p300 HAT, and solves the problems of high cytotoxicity, weak affinity, low activity and poor selectivity of existing p300 HAT small molecule inhibitors.

Method for preparing homopiperonylamine hydrochloride and berberine

The invention provides a method for preparing homopiperonylamine hydrochloride and berberine. The method for preparing homopiperonylamine hydrochloride and berberine comprises the following steps thatpiperonal is added into an organic solvent, the mixture is stirred under an ice salt bath condition, and a 2-oxazolidinone solution is dropwise added; after the reaction is completed, a reaction system is poured into an aqueous hydrochloric acid solution for hydrochlorination; the pH value is adjusted, and suction filtration is carried out to obtain the homopiperonylamine hydrochloride. The homopiperonylamine hydrochloride is prepared by the method for preparing homopiperonylamine hydrochloride and berberine. According to the homopiperonylamine hydrochloride and application, few steps, simpleoperation, no use of expensive raw materials and toxic substances, environmental protection and low cost are achieved.

Unlocking the potential of phenacyl protecting groups: CO2-based formation and photocatalytic release of caged amines

Orthogonal protection and deprotection of amines remain important tools in synthetic design as well as in chemical biology and material research applications. A robust, highly efficient, and sustainable method for the formation of phenacyl-based carbamate esters was developed using CO2 for the in situ preparation of the intermediate carbamates. Our mild and broadly applicable protocol allows for the formation of phenacyl urethanes of anilines, primary amines, including amino acids, and secondary amines in high to excellent yields. Moreover, we demonstrate the utility by a mild and convenient photocatalytic deprotection protocol using visible light. A key feature of the [Ru(bpy)3](PF6)2-catalyzed method is the use of ascorbic acid as reductive quencher in a neutral, buffered, two-phase acetonitrile/water mixture, granting fast and highly selective deprotection for all presented examples.

THE APPLICATION OF DIALKYLPHOSPHITE AS THE AMINO PROTECTION REAGENT IN ORGANIC SYNTHESIS

The acid hydrolysis of N-phenyl-N-dialkyl-phosphoramidates was studied by HPLC, the N-phenyl-N-diisopropylphosphoramidate has half life 53 min in 6N HCl at 50 deg C.The P-N bonds of these phosphoryl derivatives also show a relative stability in organic and Lewis acids.