7583-78-0

Usage

Chemical structure

Bicyclic structure containing a benzene ring and an oxepane ring

Physical state

White, crystalline solid

Molecular weight

214.3 g/mol

Applications

Potential use in organic synthesis as a building block for the preparation of various pharmacologically active compounds

Safety

Important to handle with care due to potential health hazards

Laboratory precautions

Appropriate safety measures should be taken when working with 1-benzyl-7-oxabicyclo[4.1.0]heptane in a laboratory setting

Synthetic importance

Versatile compound with significant synthetic applications

InChI:InChI=1/C13H16O/c1-2-6-11(7-3-1)10-13-9-5-4-8-12(13)14-13/h1-3,6-7,12H,4-5,8-10H2

Upstream product

• 93-59-4 Perbenzoic acid 
• 4714-09-4 1-benzylcyclohexene 
• 861316-39-4 1-benzyl-2-iodo-cyclohexanol 
• 1944-01-0 1-benzylcyclohexan-1-ol 
• 6921-34-2 benzylmagnesium chloride 

Downstream Products

• 946-33-8 2-benzylcyclohexan-1-one 
• 50648-70-9 trans-2-benzylidenecyclohexanol 
• 13694-35-4 2-benzylcyclohex-3-en-1-ol 
• 81523-04-8 1-benzyl-trans-2-methoxy-r-1-cyclohexanol 
• 81523-05-9 2-benzyl-trans-2-methoxy-r-1-cyclohexanol 
• 81523-06-0 2-benzyl-cis-2-methoxy-r-1-cyclohexanol 
• 34492-10-9 1-benzyl-r-1,t-2-cyclohexane-1,2-diol 
• 34492-11-0 1-benzyl-r-1,c-2-cyclohexane-1,2-diol 
• 227464-44-0 2-benzyl-2-bromocyclohexan-1-one 
• 81523-07-1 2-benzyl-2-methoxycyclohexanone 
• 946-33-8 (R)-2-benzylcyclohexanone 
• 946-33-8 (S)-2-benzylcyclohexanone 

Relevant academic research and scientific papers

Enantioselective protonation of samarium enolates derived from α- heterosubstituted ketones and lactone by SmI2-mediated reduction

SmI2-mediated reductive cleavage of α-heterosubstituents of α-alkyl or α-aryl ketones and lactone gave the corresponding 'thermodynamic samarium enolates'. Enantioselective protonation of the samarium enolates with C2- symmetric chiral diols afforded the corresponding ketones and lactone in moderate to high enantioselectivities.

Stereochemical Evidence for Aryl Participation in the Ring Opening of Oxiranes. Ring-Opening Reactions of 1-Benzyl-1,2-epoxycyclohexane under Acidic Conditions

The reactions of 1-benzyl-1,2-epoxycyclohexane (1) have been investigated and compared with the ones of the corresponding methyl-substituted oxirane (3) in order to evaluate the possibility that an aryl group not directly linked to the oxirane ring can participate in the ring-opening processes.The acid-catalyzed ring-opening reactions of 1 are not completly anti stereoselective and give mixtures of syn and anti addition products accompanied by rearrangement compounds.The stereoselectivity and the amounts of rearrangement products vary noticeably with the reactionconditions.The results obtained and in particular the presence of substantial amounts of syn products observed in the ring-opening reactions of 1, markedly higher than those from epoxide 3, strongly suggest the incursion of aryl participation and have been rationalized through a mechanism implying the intermediacy of a phenonium-type ion.