132452-19-8

Basic information

• Product Name: Cycloheptanone, 2-[(2-bromophenyl)methyl]-
• CAS NO: 132452-19-8
• Molecular Formula: C14H17BrO
• Molecular Weight: 281.192
• Mol File: 132452-19-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Cycloheptanone, 2-[(2-bromophenyl)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Cycloheptanone, 2-[(2-bromophenyl)methyl]-(132452-19-8)
• EPA Substance Registry System: Cycloheptanone, 2-[(2-bromophenyl)methyl]-(132452-19-8)

Safety Data

• Hazardous Substances Data: 132452-19-8(Hazardous Substances Data)

Upstream product

• 774-05-0 ethyl cycloheptanone-2-carboxylate 
• 7182-08-3 4-(1-cyclohepten-1-yl)morpholine 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 502-42-1 cycloheptanone 
• 155855-09-7 Ethyl 2-bromo-1-oxobenzylcycloheptanecarboxylate 
• 110-91-8 morpholine 

Downstream Products

• 155855-10-0 2-(o-Bromobenzyl)-1-methylenecycloheptane 
• 132452-95-0 Benzyl-[2-(2-bromo-benzyl)-cyclohept-(E)-ylidene]-amine 
• 244279-14-9 2-(2-bromophenylmethyl)-1-(phenylthiomethylene)cycloheptane 
• 155854-97-0 2-Benzyl-1-methylenecycloheptane 
• 244279-17-2 1,2,3,4,5,5a,10,10a-octahydro-5a-(phenylthiomethyl)cyclohepta[a]indene 
• 323199-58-2 4b-phenylsulfanylmethyl-4b,5,6,7,8,9,9a,10-octahydro-benzo[a]azulene 

Relevant articles and documents

Palladium-catalyzed intramolecular α-arylation of aliphatic ketone, formyl, and nitro groups

Intramolecular arylation of properly designed substrates bearing a ketone, formyl, or nitro terminating group was achieved by use of a PdCl 2(Ph3P)2-Cs2CO3 reaction system to form a variety of carbocyclic compounds. Arylation in ketone compounds afforded benzene-annulated bridged or spirocycloalkanone derivatives, depending on the structure of the cyclization precursors. Arylation in formyl compounds occurred at the α-position (α-arylation) or at the carbonyl carbon (carbonyl-arylation) depending on the structure of the cyclization precursors and on the reaction solvent. An α-arylated secondary nitro group was partially transformed to ketone in the manner of the Nef reaction, whereas a tertiary nitro group was partially eliminated to afford a styrene-type olefin. Graphical Abstract

Regiochemistry in aryl radical cyclization onto methylenecycloalkanes

Bu3SnH-mediated aryl radical cyclization onto methylenecycloalkanes having a phenylthio, an ester, or a nitrile group at the terminus of the alkenic bond provides exclusively exo cyclization products. The results are in sharp contrast to those reported for nonsubstituted methylenecycloalkanes, which give exclusively endo cyclization products. Formation of endo cyclization products has been suggested to be a result of a consecutive 5-exo cyclization of an aryl radical and neophyl rearrangement. The exo-selective aryl radical cyclization offers a new method for synthesizing fused aromatic compounds containing a benzylic quaternary carbon atom.

Regioselective Aryl Radical Cyclization. 1. Stereocontrolled Synthesis of Linearly Condensed Hydroaromatic Carbocyclic Systems through 6-endo-ring Closures

The stereocontrolled synthesis of trans-octahydroanthracenes 3, 11a-c, and 14a-c and trans-octahydro-5aH-cycloheptanaphthalene (27) through implementation of an efficient and highly regioselective 6-endo-trig-aryl radical cyclization of the respective 2-(o-bromoaryl)-1-methylenecyclohexanes 2, 10a-c, and 13a-c and 2-(o-bromobenzyl)-1-methylenecycloheptane (41) with tri-n-butyltin hydride id described.The radical cyclization of 2-(o-bromobenzyl)-1-methylenecyclopentane (43), in contrast, produced a mixture of the cis- and trans-hexahydro-1H-benzindenes (38) and (37).