7283-47-8

Basic information

• Product Name: 4,4-Dimethyl-2-phenyl-1-pentene
• Synonyms: (3,3-Dimethyl-1-methylenebutyl)benzene;4,4-Dimethyl-2-phenyl-1-pentene
• CAS NO: 7283-47-8
• Molecular Formula: C₁₃H₁₈
• Molecular Weight: 174.28
• Mol File: 7283-47-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4,4-Dimethyl-2-phenyl-1-pentene(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-Dimethyl-2-phenyl-1-pentene(7283-47-8)
• EPA Substance Registry System: 4,4-Dimethyl-2-phenyl-1-pentene(7283-47-8)

Safety Data

• Hazardous Substances Data: 7283-47-8(Hazardous Substances Data)

Upstream product

• 691-64-5 di-tert-butyl oxalate 
• 121386-57-0 methyl 2-phenylprop-2-en-1-yl carbonate 
• 6006-81-1 3-hydroxy-2-phenylpropene 
• 507-19-7 t-butyl bromide 
• 591-50-4 iodobenzene 
• 26981-77-1 t-butylallene 
• 123974-18-5 N-benzyl-2-phenyl-2-propen-1-amine 
• 56865-72-6 2-Phenyl-3-(phenylamino)-1-propene 
• 3282-30-2 pivaloyl chloride 
• 51270-89-4 1-(1-bromoethenyl)-4-methylbenzene 
• 33458-08-1 1-(1,2-dibromoethyl)-4-methylbenzene 
• 66520-90-9 2-(4-methylphenyl)-2-propen-1-ol 
• 3360-54-1 3-bromo-2-phenylprop-1-ene 
• 622-97-9 1-ethenyl-4-methylbenzene 

Downstream Products

• 1186000-52-1 [(2S)-4,4-dimethylpentan-2-yl]benzene 
• 1228632-20-9 [(2R)-4,4-dimethylpentan-2-yl]benzene 

Relevant articles and documents

Formation of allylated quaternary carbon centers: Via C-O/C-O bond fragmentation of oxalates and allyl carbonates

Disclosed herein emphasizes Fe-promoted cross-electrophile allylation of tertiary alkyl oxalates with allyl carbonates that generates all C(sp3)-quaternary centers. The reaction involves fragmentation of tertiary alkyl oxalate C-O bonds to give tertiary alkyl radical intermediates, addition of the radicals to less hindered alkene terminals, and subsequent cleavage of the allyl C-O bonds. Allylation with 2-aryl substituted allyl carbonates was mediated by Zn/MgCl2, and Fe is used to promote the radical addition efficiency. By introduction of activated alkenes, a three-component radical cascade reaction took place.

Nickel-Catalyzed Reductive Allylation of Tertiary Alkyl Halides with Allylic Carbonates

The construction of all C(sp3) quaternary centers has been successfully achieved under Ni-catalyzed cross-electrophile coupling of allylic carbonates with unactivated tertiary alkyl halides. For allylic carbonates bearing C1 or C3 substituents, the reaction affords excellent regioselectivity through the addition of alkyl groups to the unsubstituted allylic carbon terminus. The allylic alkylation method also exhibits excellent functional-group compatibility, and delivers the products with high E selectivity.

Regio- and stereoselective hydrostannation of allenes using dibutyliodotin hydride (Bu2SnIH) and successive coupling with aromatic halides

Regio- and stereoselective hydrostannation of allenes by using di-n-butyliodotin hydride (Bu2SnIH) was accomplished to give α,β-disubstituted vinyltins, which induced the synthesis of multi-substituted alkenes in a one-pot procedure. The Royal Society of Chemistry.

2-Arylallyl as a new protecting group for amines, amides and alcohols

Amines, amides and ethers containing 2-arylallyl groups are selectively and easily deprotected with tert-butyllithium. This transformation probably involves a carbolithiation reaction of the styrenyl moiety followed by a β-elimination process. The Royal Society of Chemistry 2005.

THE REACTION OF 2-ARYL-N,N-DIMETHYLALLYLIC AMINES WITH ORGANOLITHIUM REAGENTS

A variety of 2-aryl-N,N-dimethylallylic amines have been reacted with butyllithium and t-butyllithium to produce the corresponding 3-butyl and 3-t-butyl substituted 2-aryl-propenes.This procedure represents a convenient and clean method for the synthesis

EFFECTS OF LIGANDS ON ION-PAIRING BEHAVIOR OF BENZYLIC LITHIUM COMPOUNDS

The 1/1/ adduct of t-butyllithium and α-methylstyrene (II) has been generated in cyclopentane in the presence of a variety of ether and t-amine ligands as well as unsolvated, giving stable solutions in every case.NMR spectra of the solvated species are the same for all ligands but differ from that of the unsolvated compound.The results are consistent with a salt which contains a conjugated t-benzylic anion and exists as a loose ion-pair in the presence of ligands and as a tight ion-pair in cyclopentane alone.In contrast, benzyllithium behaves like a tight ion-pair in the presence of all ligands tried.Steric hindrance to tight ion-pairing at Cα of II is concluded to be responsible for the results observed.A covalently-bonded dilithium compound, 4,4-dimethyl-2-lithio-2-(p-lithio-phenyl)pentane has been generated.

Radicals from the Reaction of Hindered t-Benzyl-lithium Compounds with O2

The benzylic lithium compounds produced by 1:1 addition of t-butyl-lithium to α-methylstyrenes react with O2 to produce radicals which undergo disproportionation via hydrogen atom transfer; these unusual results are ascribed to steric hindrance about the benzyl carbon.