5617-74-3

Usage

Uses

Used in Pharmaceutical Industry:
3-Oxabicyclo[3.1.0]hexane-2,4-dione is used as a reagent in the synthesis of a newly discovered histamine H3 receptor inverse agonist. 3-Oxabicyclo[3.1.0]hexane-2,4-dione has the potential to enhance short-term memory, making it a promising candidate for the development of treatments for memory-related disorders.
Used in Chemical Synthesis:
3-Oxabicyclo[3.1.0]hexane-2,4-dione is also used in the synthesis of phthalazinone derivatives, which act as topically active phosphodiesterase 4 inhibitors. These inhibitors have potential applications in the treatment of various inflammatory and immune disorders, as well as in the development of new therapeutic agents for a range of diseases.

InChI:InChI=1/C5H4O3/c6-4-2-1-3(2)5(7)8-4/h2-3H,1H2

Upstream product

• 702-90-9 cyclopropane-1,1,2-tricarboxylic acid 
• 7605-65-4 cyclopropane-1,1,2,2-tetracarboxylic acid 
• 58616-95-8 trans-1,2-cyclopropanedicarboxylic acid 
• 878-14-8 Aethylmethyl-1,2-cyclopropandicarboxylat 
• 20561-09-5 diethyl (cis,trans)-1,2-cyclopropanedicarboxylate 
• 1489-58-3 trans-1,2-cyclopropanedicarboxylic acid 
• 696-74-2 cis-1,2-cyclopropanedicarboxylic acid 
• 710-43-0 cis-cyclopropane-1,2-dicarboxylic acid diethyl ester 
• 7605-66-5 cyclopropane-1,1,2,2-tetracarboxylic acid tetramethyl ester 
• 839-39-4 cyclopropane-1,1,2-tricarboxylic acid triethyl ester 
• 7605-64-3 tetraethyl cyclopropane-1,1,2,2-tetracarboxylate 
• 102586-88-9 (1S,8R)-1-Aza-tricyclo[6.3.2.0^2,7]trideca-2,4,6-trien-11-one 
• 702-28-3 1,2-cyclopropane dicarboxylic acid diester 

Downstream Products

• 1601-81-6 cis 2-benzoylcyclopropanecarboxylic acid 
• 710-43-0 cis-cyclopropane-1,2-dicarboxylic acid diethyl ester 
• 86331-38-6 2-((R)-2-Hydroxy-1-phenyl-ethylcarbamoyl)-cyclopropanecarboxylic acid 
• 13279-88-4 (±)-2-(methoxycarbonyl)cyclopropanecarboxylic acid 
• 188825-42-5 (+/-)-3-methyl-3,4-diazabicyclo[4.1.0]heptane-2,5-dione 
• 696-74-2 cis-1,2-cyclopropanedicarboxylic acid 
• 826-34-6 dimethyl cis-cyclopropane-1,2-dicarboxylate 
• 154186-41-1 3-(2,6-dichloro-benzyl)-3,4-diaza-bicyclo[4.1.0]heptane-2,5-dione 
• 154186-47-7 (+/-)-3-(4-methoxybenzyl)-3,4-diazabicyclo[4.1.0]heptane-2,5-dione 
• 73799-63-0 3-benzyl-3-aza-bicyclo[3.1.0]hexane-2,4-dione 
• 743438-31-5 2-(3-aza-bicyclo[3.1.0]hex-3-yl)-ethanol 

Relevant academic research and scientific papers

An efficient and improved process for the scale-up preparation of cis-cyclopropanediamine dihydrochloride

An effective and improved process for the preparation of cis-cyclopro panediamine dihydrochloride was developed in a 100 g scale. The key step in the process is the preparation of ciscyclopropane-1, 2-dicarboxylic acid from a mixture of cis- and transisomers by the formation of cyclic acidic anhydride. The whole process and all of the procedures are economical, industrially reliable and easily scaled up.

Potent non-nitrile dipeptidic dipeptidyl peptidase IV inhibitors

The synthesis and structure-activity relationships of novel dipeptidyl peptidase IV inhibitors replacing the classical cyanopyrrolidine P1 group with other small nitrogen heterocycles are described. A unique potency enhancement was achieved with β-branched natural and unnatural amino acids, particularly adamantylglycines, linked to a (2S,3R)-2,3-methanopyrrolidine based scaffold.

Design, synthesis and activity of novel derivatives of Oxybutynin and Tolterodine

Novel derivatives of Tolterodine (1) and Oxybutynin (2) have been designed using conformationally restricted azabicyclics as replacement for open-chain amines. The synthesis and structure-activity relationships are presented.

Synthesis, stereochemistry, and chiroptical spectra of cyclopropyl lactones and thionolactones

Several optically active substituted 3-oxabicyclo[3.1.0]hexan-2-ones and their thiocarbonyl analogues were synthesized, and their circular dichroism spectra are reported. It was found that the n-π* Cotton effect sign is determined by the helicity of an inherently chiral chromophore formed by the lactone or thiolactone group and the cyclopropyl moiety. The π-π* Cotton effect of thiocarbonyl compounds shows opposite sign to that observed for the lowest energy transition. The crystal structures of two compounds were solved to establish their molecular geometries. Copyright (C) Elsevier Science Ltd.

ENZYMATIC RESOLUTION OF RACEMIC BICYCLIC LACTONES BY HORSE LIVER ESTREASE

Optically active lactones were prepared by Horse Liver esterase catalyzed hydrolysis of bicyclic γ-butyrolactones.

The Synthesis and Cycloaddition Reactions of 3-Azabicyclohex-2-ene 3-oxide and 3-Azabicyclohept-2-ene 3-oxide. Highly Strained Bicyclic Nitrones

The synthesis of two strained bicyclic nitrones is described.Subsequent cycloadditions demonstrated a high degree of regiochemical and stereochemical control.

A Study of Stereoselective Hydrolysis of Symmetrical Diesters with Pig Liver Esterase

Pig liver esterase (PLE) catalyzed hydrolysis of dimethyl esters of symmetrical dicarboxylic acids, including meso-diacids, cis-1,2-cycloalkanedicarboxylic acids, and diacids with a prochiral center, was studied with 14 substrates.The products of these stereoselective hydrolyses are chiral monoesters of dicarboxylic acids, with an enantiomeric excess (e.e.) from 10percent to 100percent.Some of these optically active monoesters are valuable synthons in natural products synthesis.An additivity pattern of α- and β-substituents with the glutaric esters on the stereoselectivity of enzymatic hydrolysis was observed.Analysis of the experimental results leads to a model of enzyme stereoselectivity of diester hydrolysis in which the substitution pattern at α- and β-C-atoms is found to determine the absolute configuration of the resulting monoester.