40458-77-3

Basic information

• Product Name: 8-oxa-bicyclo[3.2.1]oct-6-en-3-one
• Synonyms: 8-oxa-bicyclo[3.2.1]oct-6-en-3-one
• CAS NO: 40458-77-3
• Molecular Formula: C₇H₈O₂
• Molecular Weight: 124.13722
• Mol File: 40458-77-3.mol

Chemical Properties

• Melting Point: 36-38 °C
• Boiling Point: 110-130 °C(Press: 11 Torr)
• Appearance: /
• Density: 1.196±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 8-oxa-bicyclo[3.2.1]oct-6-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 8-oxa-bicyclo[3.2.1]oct-6-en-3-one(40458-77-3)
• EPA Substance Registry System: 8-oxa-bicyclo[3.2.1]oct-6-en-3-one(40458-77-3)

Safety Data

• Hazardous Substances Data: 40458-77-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
8-oxa-bicyclo[3.2.1]oct-6-en-3-one is utilized as a key intermediate in the synthesis of pharmaceuticals due to its potential to form diverse chemical entities with therapeutic properties. Its unique structure and reactivity allow for the development of new drugs with novel mechanisms of action.
Used in Agrochemical Development:
In the agrochemical industry, 8-oxa-bicyclo[3.2.1]oct-6-en-3-one serves as a building block for the creation of new pesticides or herbicides. Its structural features can be leveraged to design molecules with enhanced biological activity and selectivity, contributing to more effective and environmentally friendly agricultural products.
Used in Chemical Industry for Material Synthesis:
8-oxa-bicyclo[3.2.1]oct-6-en-3-one is employed as a versatile precursor in the chemical industry for the synthesis of various materials. Its ketone functionality can be modified to produce a range of compounds with different properties, suitable for applications in coatings, polymers, and other advanced materials.
Used in Organic Synthesis:
As a heterocyclic compound with a reactive ketone group, 8-oxa-bicyclo[3.2.1]oct-6-en-3-one is used in organic synthesis for the preparation of complex organic molecules. Its ability to participate in various chemical reactions makes it a valuable tool for the construction of intricate molecular frameworks.

Upstream product

• 109-99-9 tetrahydrofuran 
• 632-21-3 1,1,3,3-tetrachloropropanone 
• 110-00-9 furan 
• 26562-24-3 3-bromo-2-methoxypropene 
• 22612-89-1 1,1,3,3-tetrabromoacetone 
• 557-20-0 diethylzinc 
• 1768-31-6 pentachloroacetone 
• 79763-03-4 2,2,4-endo-trichloro-8-oxabicyclo<3.2.1>oct-6-en-3-one 
• 79763-02-3 endo-2,endo-4-Dichlor-8-oxabicyclo<3.2.1>oct-6-en-3-on 
• 55076-42-1 2,4-dibromo-8-oxabicyclo<3.2.1>oct-6-en-3-one 
• 82521-32-2 2,2,4,4-Tetrachlor-8-oxabicyclo<3.2.1>oct-6-en-3-on 
• 58986-98-4 2,2,4-Tribromo-8-oxa-bicyclo[3.2.1]oct-6-en-3-one 

Downstream Products

• 222172-07-8 (1R,3R,5S,6R)-3-(4-methoxybenzyl)-oxy-8-oxa-bicyclo<3.2.1>octan-6-ol 
• 197379-09-2 (1R,3R,5S)-3-Benzyloxy-8-oxa-bicyclo[3.2.1]oct-6-ene 
• 92591-75-8 3-<(N-methylphenylsulphonimidoyl)methyl>-exo-2-<7-(tetrahydropyran-2-yloxy)heptyl>-8-oxabicyclo<3.2.1>octan-3-ol 

Relevant articles and documents

Accessing tetrahydrofuran-based natural products by microbial Baeyer-Villiger biooxidation

A heterobicyclic lactone obtained by stereoselective Baeyer-Villiger biooxidation with recombinant whole-cells expressing cyclopentanone monooxygenase from Comamonas sp. NCIMB 9872 was used for formal total syntheses of various natural products containing

Discovery of MK-6169, a Potent Pan-Genotype Hepatitis C Virus NS5A Inhibitor with Optimized Activity against Common Resistance-Associated Substitutions

We describe the discovery of MK-6169, a potent and pan-genotype hepatitis C virus NS5A inhibitor with optimized activity against common resistance-associated substitutions. SAR studies around the combination of changes to both the valine and aminal carbon region of elbasvir led to the discovery of a series of compounds with substantially improved potency against common resistance-associated substitutions in the major genotypes, as well as good pharmacokinetics in both rat and dog. Through further optimization of key leads from this effort, MK-6169 (21) was discovered as a preclinical candidate for further development.

Synthesis of tetrahydrofuran-based natural products and their carba analogs via stereoselective enzyme mediated Baeyer–Villiger oxidation

In this work we present efficient formal syntheses of several biologically interesting natural products (showdomycin, goniofufurone, trans-kumausyne) and their novel carba analogs by applying different Baeyer–Villiger monooxygenases. This strategy provides access to tetrahydrofuran-based natural products, C-nucleosides and both antipodes of the corresponding carba analogs in high optical purities (up to >95% ee) starting from simple achiral and commercially available building blocks (tetrabromoacetone, furan and cyclopentadiene). The striking key features of this chemo-enzymatic approach are the introduction of four stereogenic centers in as few as three reaction steps within a desymmetrization approach and the short-cut of several reaction sequences by the implementation of a biocatalytic step.

Functional characterization of recombinant hyoscyamine 6β-hydroxylase from Atropa belladonna

(-)-Hyoscyamine, the enantiomerically pure form of atropine, and its derivative scopolamine are tropane alkaloids that are extensively used in medicine. Hyoscyamine 6β-hydroxylase (H6H, EC 1.14.11.11), a monomeric α-ketoglutarate dependent dioxygenase, converts (-)-hyoscyamine to its 6,7-epoxy derivative, scopolamine, in two sequential steps. In this study, H6H of Atropa belladonna (AbH6H) was cloned, heterologously expressed in Escherichia coli, purified and characterized. The catalytic efficiency of AbH6H, especially for the second oxidation, was found to be low, and this may be one of the reasons why Atropa belladonna produces less scopolamine than other species in the same family. 6,7-Dehydrohyoscyamine, a potential precursor for the last step of epoxidation, was shown not to be an obligatory intermediate in the biosynthesis of scopolamine using purified AbH6H with an in vitro 18O labeling experiment. Moreover, the nitrogen atom in the tropane ring of (-)-hyoscyamine was found to play an important role in substrate recognition.

HEPATITIS C VIRUS INHIBITORS

The present disclosure relates to compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment o

Facile synthesis and ring-opening cross metathesis of carbo- and heterocyclic bicyclo[3.2.1]oct-6-en-3-ones using gaseous olefinic reaction partners

The title compounds were prepared by a facile [4+3]-cycloaddition strategy involving sonochemistry. The oxyallyl species required for the reaction with the corresponding diene was generated from a suitable perbromo ketone with activated zinc under sonific

Synthesis of the C38-C44 segment of altohyrtin A - with an addendum on the preparation of 8-oxabicyclo[3,2.1]oct-6-en-3-one

The densely funtionalized C38-C44 segment F of altohyrtin A with its five contiguous stereogenic centers was prepared in 10 steps and in 28% overall yield (two steps per stereogenic center), from 8- oxabicyclo[3.2.1]oct-6-en-3-one as a template. The preparation of the title compound 1, m.p. 38 °C, is described on a 0.5 m scale in a three-step-two- stage reaction from acetone anti furan. The oxacycle was stored without change at room temperature.

Synthesis of 8-oxa analogues of norcocaine endowed with interesting cocaine-like activity

In order to further explore the importance of cocaine's bridge nitrogen atom in binding to the dopamine transporter (DAT), we have synthesized the previously known racemic 8-oxa-norcocaines 3-6 in which the nitrogen atom has been replaced by oxygen. Additionally, to avoid incorrect interpretations of biological data that may stem from the use of racemic materials, several of these analogues were synthesized and tested in non-racemic form. (-)-8-Oxa- norcocaine (3) was found to bind to the cocaine recognition site and to inhibit the dopamine transporter with potencies only about 8-fold and 4- fold, respectively, less than those of norcocaine (2). (-)-8-Oxa- pseudonorcocaine (4) as well as (+)-8-oxa-norcocaine (3) were found to be comparable in activity to (-)-oxa-norcocaine. These pharmacological findings support our earlier suggestion that cocaine is likely to bind in its neutral form to the DAT.

Asymmetric synthesis of polyacetate derived building clocks with α- oxyanion functionality. Lewis acid catalyzed opening of 2,9- dioxabicyclo[3.3.1]nonan-3-ones

All four stereoisomeric cyclic 3,5,7-trihydroxyheptanoic acid equivalents of the polyacetate aldol type (Scheme 1) are obtainable from 8- oxabicyclo[3.2.1]oct-6-en-3-one which functions as a meso-configurated 4-way optical switch. Lewis acid assisted nucl

HIGHLY STEREOSELECTIVE, TOTAL SYNTHESIS OF β-C-HEXOPYRANOSYL DERIVATIVES

One Diels-Alder adduct of furan to 1-cyanovinyl acetate is converted to 8-oxabicyclooct-6-en-2-one which is transformed into β-C-hexopyranosides including 2-deoxy and 2,3-unsaturated derivatives.