128649-19-4

Basic information

• Product Name: (Z)-α-butylcinnamaldehyde
• Synonyms: (Z)-α-butylcinnamaldehyde
• CAS NO: 128649-19-4
• Molecular Weight: 188.269
• Mol File: 128649-19-4.mol

Chemical Properties

• CAS DataBase Reference: (Z)-α-butylcinnamaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-α-butylcinnamaldehyde(128649-19-4)
• EPA Substance Registry System: (Z)-α-butylcinnamaldehyde(128649-19-4)

Safety Data

• Hazardous Substances Data: 128649-19-4(Hazardous Substances Data)

Upstream product

• 85260-47-5 cis-2-(1'-butyl)-1-(trimethylsilyl)oxirane 
• 100-52-7 benzaldehyde 
• 904295-67-6 α,α-bis(trimethylsilyl)-N-tert-butylhexanaldimine 
• 100-44-7 benzyl chloride 
• 66-25-1 hexanal 
• 128649-15-0 N-(2-benzyl-2-chloro-1-hexylidene)t-butylamine 
• 128649-14-9 N-(2-benzyl-1-hexylidene)t-butylamine 
• 56951-64-5 N-(1-hexylidene)t-butylamine 
• 56951-64-5 N-tert-butylhexan-1-imine 
• 128649-16-1 N-(2-butyl-3-phenyl-2-propen-1-ylidene)t-butylamine 
• 84395-69-7 1-[(1E)-hex-1-en-1-yl]piperidine 
• 774-48-1 (diethoxymethyl)benzene 

Downstream Products

• 1055718-10-9 2-butyl-3-phenyl-allyl alcohol 

Relevant articles and documents

REGIOSPECIFIC RING CLEAVAGE OF α,β-EPOXYSILANES TO FORM TRANSITION METAL ENOLATE INTERMEDIATES

Molybdenum(II) acetate dimer or titanium(IV) i-propoxide induced regiospecific ring cleavage of α,β-epoxysilanes to form the enolate intermediates, which reacted with aldehydes to give the corresponding α,β-unsaturated carbonyl compounds.

A general route to α-alkyl (E)-α,β-unsaturated aldehydes

Bis(trimethylsilyl)-tert-butylaldimines 3 react with aldehydes in the presence of zinc bromide at room temperature to give, after hydrolysis, the desired α-alkyl α,β-ethylenic aldehydes in good yield and with very high E stereoselectivity. The reaction was believed to proceed via the α-silyl β-siloxyimines 4.

OXIDATION OF ALDEHYDES TO α,β-UNSATURATED ALDEHYDES VIA α-CHLOROALDIMINES

The oxidation of aldehydes to α,β-unsaturated aldehydes has been performed by a sequence of reactions involving conversion into aldimines, chlorination at the α-position to form α-chloroaldimines, base-induced dehydrochlorination and hydrolysis.The four-step transformation can be executed without isolation of the intermediates.This method has been applied to the synthesis of an artificial flavor, i.e. 2-butyl-3-phenylpropenal.

Reaction of Enamines with Acetals or Trialkyl Orthoformates Activated by Lewis Acids

Enamines, prepared readily from various carbonyl compounds, react with acetals or trialkyl orthoformates in the presence of Lewis acids such as BF3.OEt2 to give corresponding β-alkoxy carbonyl compounds or α-dialkoxymethyl carbonyl compounds in good yields.The reaction of dienamines with acetals or trialkyl orthoformates also selectively gives corresponding β,χ-unsaturated α-(α-alkoxyalkyl) carbonyl compounds or β,χ-unsatureted α-dialkoxymethyl carbonyl compounds in good yields.

REACTION OF ENOLATES OF ACYLTRIMETHYLSILANES WITH ALDEHYDES. CANNIZZARO TYPE OXIDATION-REDUCTION REACTION WITH A TRIMETHYLSILYLCARBONYL GROUP

The reaction of an acyltrimethylsilane enolate with 2 eq of an aldehyde gives a 1:2 adduct, while that with the enolate of an α-chloroacyltrimethylsilane affords an α,β-unsaturated aldehyde as a 1:1 adduct accompanied by the carboxylic acid derived from the starting aldehyde.An oxidation-reduction reaction mechanism on the trimethylsilylcarbonyl group has been proposed.