61946-94-9

Basic information

• Product Name: 1,3-Benzodioxole-5-carboximidoyl chloride, N-hydroxy-
• CAS NO: 61946-94-9
• Molecular Formula: C8H6ClNO3
• Molecular Weight: 199.594
• Mol File: 61946-94-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,3-Benzodioxole-5-carboximidoyl chloride, N-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Benzodioxole-5-carboximidoyl chloride, N-hydroxy-(61946-94-9)
• EPA Substance Registry System: 1,3-Benzodioxole-5-carboximidoyl chloride, N-hydroxy-(61946-94-9)

Safety Data

• Hazardous Substances Data: 61946-94-9(Hazardous Substances Data)

Upstream product

• 2089-36-3 (E)-3,4-methylenedioxybenzaldehyde oxime 
• 20747-42-6 piperonal-(Z)-oxime 

Downstream Products

• 81410-45-9 (8R,8'R-)8,8'-bis-(3'4'-methylenedioxybenzyl)-tetrahydrofuran (-)-dehydroxycubebin 
• 23284-23-3 (+)-trans-burseran 
• 73465-36-8 (-)-(3R,4R)-3-(3,4-methylenedioxybenzyl)-4-(3,4,5-trimethoxybenzyl)tetrahydrofuran 
• 83727-24-6 Methyl 2-<3-(3,4-methylenedioxyphenyl)-2-isoxazolin-5-yl>benzoate 
• 438565-34-5 (3-(benzo[d][1,3]dioxol-5-yl)isoxazol-5-yl)methanol 
• 25856-13-7 3-(benzo[d][1,3]dioxol-5-yl)-5-phenylisoxazole 

Relevant articles and documents

Synthesis and SAR of new isoxazole-triazole bis-heterocyclic compounds as analogues of natural lignans with antiparasitic activity

Despite the impressive scientific and technological advances of recent decades, no effective treatment is currently available for Chagas disease. Our research group has been studying the design and synthesis of analogues of natural lignans aiming to identify compounds with antiparasitic activity. This article reports the synthesis of 42 novel bis-heterocyclic derivatives and the structure-activity relationship study conducted based on results of biological assays against Trypanosoma cruzi amastigotes. Thirty-seven compounds were active, and eight of them had GI50 values lower than 100 μM (GI50 88.4–12.2 μM). A qualitative structure activity relationship study using three dimensional descriptors was carried out and showed a correlation between growth inhibitory potency and the presence of bulky hydrophobic groups located at rings A and D of the compounds. Compound 3-(3,4-dimethoxyphenyl)-5-((4-(4-pentylphenyl)-1H-1,2,3-triazol-1-yl)methyl)isoxazole (31) was the most active in the series (GI50 12.2 μM), showing, in vitro, low toxicity and potency similar to benznidazole (GI50 10.2 μM). These results suggest that this compound can be a promising scaffold for the design of new trypanocidal compounds.

Regioselective synthesis of C-nucleosides by 1,3-dipolar cycloaddition of arylnitrile oxides to 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose

The synthesis of 3-aryl-5-(1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-2-isoxazoline (3) from arylnitrile oxides and 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose (1) is described.The 1,3-dipolar cycloaddition reactions give mainly anti-adducts (>=95percent ?-facial stereoselectivity).

AN IMPROVED PROCEDURE FOR THE PREPARATION OF 2-ISOXAZOLINES

Aldoximes were converted in high yields by N-Chlorosuccinimide into hydroxamic acid chlorides, and corresponding nitrile oxides generated by addition of triethylamine at 40-50 deg C underwent 1,3-dipolar addition to alkenes, giving 2-isoxazolines.The whole procedure could be performed as a one-pot reaction.Oximes with other functions, sensitive to free chlorine could be converted selectively into hydroxamic acid chlorides by this procedure.Isopropylidene glyceraldoxime was added to acrolein diethylacetal thus affording an entrance to carbohydrate synthesis but the stereospecificity of the reaction is low. 2:3, 5:6-Di-O-isopropylidene-D- mannose oxime was converted to the N-hydroximinolactone by treatment with NCS and base.