58774-33-7

Basic information

• Product Name: 3,4-dibromo-7-oxabicyclo[4.1.0]heptane
• Synonyms: 3,4-dibromo-7-oxabicyclo[4.1.0]heptane
• CAS NO: 58774-33-7
• Molecular Formula: C₆H₈Br₂O
• Molecular Weight: 255.93512
• Mol File: 58774-33-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 260 °C at 760 mmHg
• Flash Point: 102.7 °C
• Appearance: /
• Density: 2.047 g/cm³
• Vapor Pressure: 0.0203mmHg at 25°C
• Refractive Index: 1.602
• CAS DataBase Reference: 3,4-dibromo-7-oxabicyclo[4.1.0]heptane(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dibromo-7-oxabicyclo[4.1.0]heptane(58774-33-7)
• EPA Substance Registry System: 3,4-dibromo-7-oxabicyclo[4.1.0]heptane(58774-33-7)

Safety Data

• Hazardous Substances Data: 58774-33-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H8Br2O/c7-3-1-5-6(9-5)2-4(3)8/h3-6H,1-2H2

Upstream product

• 42846-36-6 dibromocyclohexene 
• 6253-27-6 cis-1,2-epoxy-4-cyclohexene 
• 1165952-92-0 cyclohexa-1,4-diene 
• 42846-36-6 trans-4,5-dibromo-1-cyclohexene 
• 286-20-4 cyclohexane-1,2-epoxide 
• 6253-27-6 4,5-epoxy-cyclohexene 
• 62199-53-5 4,5-dibromocyclohexene 
• 93-59-4 Perbenzoic acid 

Downstream Products

• 1488-25-1 benzene oxide 
• 321164-63-0 (1RS,2SR,3RS,4SR)-4-aminocyclohexane-1,2,3-triol 
• 138513-21-0 (1S,2R,3S,6R)-6-aminocyclohex-4-ene-1,2,3-triol 
• 108-95-2 phenol 

Relevant articles and documents

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Synthesis of (-)-Conduramine A1, (-)-Conduramine A2 and (-)-Conduramine E2 in Six Steps from Cyclohexa-1,4-diene

A method to enable the synthesis of conduramines and their N-substituted derivatives (enantiopure or racemic form) in six steps (five steps for N-substituted derivatives) from cyclohexa-1,4-diene is reported. Key features of this reaction sequence include a preparation of benzene oxide that is amenable to multigram scale, and its efficient ring-opening upon treatment with a primary amine. Epoxidation of the resultant amino alcohols (40% aq HBF4 then m-CPBA) is accompanied by hydrolytic ring-opening in situ to give the corresponding N-substituted conduramine derivatives directly. These may undergo subsequent N-deprotection to give the parent conduramines, as demonstrated by the preparation of enantiopure (-)-conduramine A1, (-)-conduramine A2, and (-)-conduramine E2 (the latter two for the first time). The selectivity of the epoxidation reaction is proposed to be the result of competitive ammonium-directed and hydroxyl-directed epoxidation processes, followed by either direct (SN2-type) or conjugate (SN2′-type) ring-openings of the intermediate epoxides.

Synthesis and Desymmetrization of meso Tricyclic Systems Derived from Benzene Oxide

Ozonolysis of the Diels-Alder adducts derived from benzene oxides and N-alkylmaleimides resulted in fully substituted, meso bicyclic systems bearing six contiguous stereocenters, isolated as diols upon reductive workup with NaBH4. Variation in the workup allowed for isolation of two different diastereoisomers, through double epimerization of the imide stereocenters. Desymmetrization of the resulting meso diols via asymmetric nucleophilic epoxide opening and acylation reactions provided access to highly substituted, enantioenriched fused rings.