29179-15-5

Basic information

• Product Name: 3,5-Hexadien-2-one, 6-phenyl-, (Z,E)-
• CAS NO: 29179-15-5
• Molecular Formula: C12H12O
• Molecular Weight: 172.227
• Mol File: 29179-15-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3,5-Hexadien-2-one, 6-phenyl-, (Z,E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Hexadien-2-one, 6-phenyl-, (Z,E)-(29179-15-5)
• EPA Substance Registry System: 3,5-Hexadien-2-one, 6-phenyl-, (Z,E)-(29179-15-5)

Safety Data

• Hazardous Substances Data: 29179-15-5(Hazardous Substances Data)

Upstream product

• 1552-94-9 (2Z,4E)-5-phenylpenta-2,4-dienoic acid 
• 917-54-4 methyllithium 
• 14371-10-9 (E)-3-phenylpropenal 
• 108-22-5 Isopropenyl acetate 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 67-64-1 acetone 

Downstream Products

• 14171-89-2 1-phenyl-5-hexanone 
• 33599-88-1 (E)-6-phenylhex-5-en-2-one 
• 1408280-77-2 (E)-dimethyl 4-methyl-6-styrylisophthalate 
• 1353719-46-6 (S)-5-methyl-5-((R,E)-5-oxo-1-phenylhex-1-en-3-yl)-2-phenyloxazol-4(5H)-one 
• 1293997-44-0 (S)-tert-butyl 2-oxo-5-((S,E)-5-oxo-1-phenylhex-1-en-3-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 1209466-54-5 (E)-4-(nitromethyl)-6-phenylhex-5-en-2-one 
• 1165944-75-1 (S)-(E)-4-(nitromethyl)-6-phenyl-5-hexen-2-one 
• 78925-42-5 1-(3-hydroxy-4-methoxyphenyl)-7-phenyl-3-heptanone 

Relevant articles and documents

Synthesis of Polysubstituted Pyridines via a One-Pot Metal-Free Strategy

An efficient strategy for the one-pot synthesis of polysubstituted pyridines via a cascade reaction from aldehydes, phosphorus ylides, and propargyl azide is reported. The reaction sequence involves a Wittig reaction, a Staudinger reaction, an aza-Wittig reaction, a 6π-3-azatriene electrocyclization, and a 1,3-H shift. This protocol provides quick access to the polysubstituted pyridines from readily available substrates in good to excellent yields.

Wittig reactions in the ionic solvent [bmim][BF4]

The ionic salt [bmim][BF4] is an attractive solvent for Wittig reactions, allowing both easier separation of alkenes from Ph3PO together with eficient reuse to the solvent.

Synthesis of diarylheptanoids and assessment of their pungency

With the aim of correlating pungency with substituent groups on one benzene ring, various analogues of yakuchinones were synthesized by means of the Claisen-Schmidt reaction. Their pungencies were assessed by direct comparison of the threshold concentrations obtained in taste experiments. The presence of a phenolic hydroxyl group was indispensable for high pungency, while that of a 1,2-double bond of the heptanone part tended to decrease the pungency.