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
• Article Data: 23

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

General Description

8-oxa-bicyclo[3.2.1]oct-6-en-3-one, also known as 3-oxabicyclo[3.2.1]oct-6-en-3-one, is a compound with a bicyclic structure containing an oxygen atom and a ketone functional group. It is a heterocyclic compound with potential uses in organic synthesis and pharmaceutical research. The bicyclic structure of the compound provides a unique three-dimensional shape that can be utilized in the design of new drugs and biologically active molecules. Additionally, the presence of the ketone functional group makes it a versatile building block for the synthesis of various chemical compounds. Its potential applications include the development of new pharmaceuticals, agrochemicals, and materials in the chemical industry.

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 
• 82521-32-2 2,2,4,4-Tetrachlor-8-oxabicyclo<3.2.1>oct-6-en-3-on 
• 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 
• 58986-98-4 2,2,4-Tribromo-8-oxa-bicyclo[3.2.1]oct-6-en-3-one 

Downstream Products

• 76763-49-0 Benzoic acid (1R,5R,6S)-3-oxo-8-oxa-bicyclo[3.2.1]oct-6-yl ester 
• 1142364-47-3 4-cyano-N-(2-(4,4-dimethylcyclohex-1-enyl)-4-((3-exo)-3-hydroxy-8-oxabicyclo[3.2.1]oct-6-en-3-yl)phenyl)-1H-imidazole-2-carboxamide 
• 77745-32-5 (1α-H,5α-H)-8-Oxabicyclo<3.2.1>octan-3-on 
• 69496-58-8 8-Oxabicyclo<3.2.1>oct-6-en-3-one Oxime Tosylate 
• 139519-69-0 N-<(1-αH,5-αH)-8-Oxabicyclo<3.2.1>octan-3α-yl>N-phenylpropanamid 
• 139519-70-3 N-<(1-αH,5-αH)-8-Oxabicyclo<3.2.1>octan-3β-yl>N-phenylpropanamid 
• 139519-67-8 N-<(1-αH,5-αH)-8-Oxabicyclo<3.2.1>oct-6-en-3α-yl>N-phenyl-propanamid 
• 139519-68-9 N-<(1-αH,5-αH)-8-Oxabicyclo<3.2.1>oct-6-en-3β-yl>N-phenylpropanamid 
• 139519-71-4 N-<(1-αH,5-αH)-8-Oxabicyclo<3.2.1>octan-3α-yl>N-propylanilin 
• 139519-72-5 N-<(1-αH,5-αH)-8-Oxabicyclo<3.2.1>octan-3β-yl>N-propylanilin 
• 139519-64-5 N-Phenyl-(1α-H,5α-H)-8-oxabicyclo<3.2.1>octan-3α-amin 

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

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.

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