105251-34-1

Basic information

• Product Name: (3S*,4S*)-4-amino-3-methyl-4-phenyl-1-butene
• Synonyms: (3S*,4S*)-4-amino-3-methyl-4-phenyl-1-butene
• CAS NO: 105251-34-1
• Molecular Weight: 161.247
• Mol File: 105251-34-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (3S*,4S*)-4-amino-3-methyl-4-phenyl-1-butene(CAS DataBase Reference)
• NIST Chemistry Reference: (3S*,4S*)-4-amino-3-methyl-4-phenyl-1-butene(105251-34-1)
• EPA Substance Registry System: (3S*,4S*)-4-amino-3-methyl-4-phenyl-1-butene(105251-34-1)

Safety Data

• Hazardous Substances Data: 105251-34-1(Hazardous Substances Data)

Upstream product

• 167773-12-8 2-<(2E/Z)-2-butenyl>-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 100-52-7 benzaldehyde 
• 69611-02-5 (E)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 100-46-9 benzylamine 
• 941278-25-7 (E)-but-2-en-1-yl tert-butyl carbonate 
• 973-59-1 2,6-di-tert-butyl-4-(benzylideneamino)phenol 
• 622-79-7 benzyl azide 
• 14850-89-6 (E)-N'-benzylidenebenzohydrazide 
• 878193-80-7 (E)-2-(benzylideneamino)-4-methylphenol 
• 1039032-31-9 (4S*)-4-hydroxylamino-3-methyl-4-phenyl-1-butene 
• 25201-44-9 2-methyl-1-phenyl-3-butene-1-ol 

Relevant articles and documents

The first allylation of imines with allyltrichlorosilanes using neutral coordinate-organocatalysts

Imines derived from aldehydes and 2-aminophenols reacted with allyltrichlorosilanes in the presence of DMF, HMPA, or pyridine N-oxide as a neutral coordinate-organocatalyst to afford the corresponding homoallylic amines in high yields with high stereosele

Formal α-Allylation of Primary Amines by a Dearomative, Palladium-Catalyzed Umpolung Allylation of N-(Aryloxy)imines

N-(Aryloxy)imines, readily accessible by condensation/tautomerization of (pseudo)benzylic primary amines and 2,6-di-tert-butyl-1,4-benzoquinone, undergo efficient allylation to afford a wide range of homoallylic primary amines following hydrolytic workup. Deprotonation of N-(aryloxy)imines generates a delocalized 2-azaallyl anion-type nucleophile that engages in dearomative C-C bond-forming reactions with allylpalladium(II) electrophiles generated from allylic tert-butyl carbonates. This reactivity umpolung enables the formal α-allylation of (pseudo)benzylic primary amines. Mechanistic studies reveal that the apparent regioselectivity of the desired bond-forming event is a convergent process that is initiated by unselective allylation of N-(aryloxy)imines to give several regioisomeric species, which subsequently rearrange via stepwise [1,3]- or concerted [3,3]-sigmatropic shifts, ultimately converging to provide the desired regioisomer of the amine products.

Allylboronation of imines: 1-Phenylhex-5-en-3-amine

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