33070-04-1

Usage

Carboxylic acid amide derivative

It is a type of organic compound that contains a carbonyl group (C=O) attached to an amine group (NH2). This structure endows the compound with specific chemical properties and potential reactivity.

Structural features

The compound has a 2,3-dihydro-benzo[1,4]dioxine core structure, which may contribute to its potential biological activities and applications in pharmaceutical research.

Potential applications

2,3-Dihydro-benzo[1,4]dioxine-2-carboxylic acid amide may have potential applications in pharmaceutical research and drug development due to its unique structure and possible biological activities.

Further research and testing needed

To fully understand the properties and potential uses of this chemical compound, additional research and testing would be required in various industries. This includes examining its stability, solubility, and reactivity with other compounds, as well as evaluating its potential therapeutic effects and safety profile.

InChI:InChI=1/C9H9NO3/c10-9(11)8-5-12-6-3-1-2-4-7(6)13-8/h1-4,8H,5H2,(H2,10,11)/t8-/m1/s1

Upstream product

• 120-80-9 benzene-1,2-diol 
• 1008-92-0 2-cyano-1,4-benzodioxane 
• 1616377-88-8 rac-2-N,N-dichloroaminomethyl-1,4-benzodioxane 
• 4442-59-5 (2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)amine 
• 4739-94-0 ethyl 2,3-dihydro-1,4-benzodioxin-2-carboxylate 

Relevant academic research and scientific papers

Characterization of an indole-3-acetamide hydrolase from alcaligenes faecalis subsp. parafaecalis and its application in efficient preparation of both enantiomers of chiral building block 2,3-dihydro-1,4-benzodioxin-2-carboxylic acid

Both the enantiomers of 2,3-dihydro-1,4-benzodioxin-2-carboxylic acid are valuable chiral synthons for enantiospecific synthesis of therapeutic agents such as (S)-doxazosin mesylate, WB 4101, MKC 242, 2,3-dihydro-2-hydroxymethyl-1,4-benzodioxin, and N-[2,4-oxo-1,3-thiazolidin-3-yl]-2,3-dihydro-1,4-benzodioxin-2-carboxamide. Pharmaceutical applications require these enantiomers in optically pure form. However, currently available methods suffer from one drawback or other, such as low efficiency, uncommon and not so easily accessible chiral resolving agent and less than optimal enantiomeric purity. Our interest in finding a biocatalyst for efficient production of enantiomerically pure 2,3-dihydro-1,4-benzodioxin-2-carboxylic acid lead us to discover an amidase activity from Alcaligenes faecalis subsp. parafaecalis, which was able to kinetically resolve 2,3-dihydro-1,4-benzodioxin-2-carboxyamide with E value of >200. Thus, at about 50% conversion, (R)-2,3-dihydro-1,4-benzodioxin-2-carboxylic acid was produced in >99% e.e. The remaining amide had (S)-configuration and 99% e.e. The amide and acid were easily separated by aqueous (alkaline)-organic two phase extraction method. The same amidase was able to catalyse, albeit at much lower rate the hydrolysis of (S)-amide to (S)-acid without loss of e.e. The amidase activity was identified as indole-3-acetamide hydrolase (IaaH). IaaH is known to catalyse conversion of indole-3-acetamide (IAM) to indole-3-acetic acid (IAA), which is phytohormone of auxin class and is widespread among plants and bacteria that inhabit plant rhizosphere. IaaH exhibited high activity for 2,3-dihydro-1,4-benzodioxin-2-carboxamide, which was about 65% compared to its natural substrate, indole-3-acetamide. The natural substrate for IaaH indole-3-acetamide shared, at least in part a similar bicyclic structure with 2,3-dihydro-1,4-benzodioxin-2-carboxamide, which may account for high activity of enzyme towards this un-natural substrate. To the best of our knowledge this is the first application of IaaH in production of industrially important molecules.

From 2-aminomethyl-1,4-benzodioxane enantiomers to unichiral 2-cyano- and 2-carbonyl-substituted benzodioxanes via dichloroamine

2-Substituted 1,4-benzodioxanes, such as 2-cyano-, 2-methoxycarbonyl-, 2-aminocarbonyl-, and 2-formyl-1,4-benzodioxane, are key synthons that for the most part are never described as enantiomers or are inadequately characterized for enantiomeric purity. They were prepared by quantitative N,N-dichlorination of (R)- and (S)-2-aminomethyl-1,4-benzodioxane and successive functional group conversions in high yields without any racemization of the stereogenic benzodioxane C(2).