14771-80-3

Basic information

• Product Name: 3-benzyl-4-methyl-3-penten-2-one
• Synonyms: 3-benzyl-4-methyl-3-penten-2-one
• CAS NO: 14771-80-3
• Molecular Weight: 188.269
• Mol File: 14771-80-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-benzyl-4-methyl-3-penten-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-benzyl-4-methyl-3-penten-2-one(14771-80-3)
• EPA Substance Registry System: 3-benzyl-4-methyl-3-penten-2-one(14771-80-3)

Safety Data

• Hazardous Substances Data: 14771-80-3(Hazardous Substances Data)

Upstream product

• 141-79-7 4-methyl-pent-3-en-2-one 
• 100-44-7 benzyl chloride 
• 14988-33-1 4,6-dimethyl-5-benzyl-2-pyrone 
• 3744-02-3 4-methylpent-4-en-2-one 
• 100-39-0 benzyl bromide 

Downstream Products

• 13380-80-8 2-benzyl-3-methyl-2-cyclopenten-1-one 
• 136638-88-5 2-benzyl-3,5-dimethyl-5-(phenylseleno)cyclopent-2-enone 
• 136638-85-2 2-benzyl-3-methyl-5-(phenylseleno)cyclopent-2-enone 
• 136638-89-6 2-benzyl-3-methyl-5-methylenecyclopent-2-enone 
• 131353-08-7 3-benzyl-3-chloro-4-methyl-4-penten-2-one 

Relevant articles and documents

Base-Induced Cyclization of α-Chloro- β,γ-Unsatured Ketones. Facile Synthesis of Tri- and Tetrasubstituted 2-Cyclopenten-1-ones

Base-induced cyclization of fully substituted α-chloro β,γ-unsatured ketones results in substituted cyclopentenones.Potassium tert-butoxyde, lithium diisopropylamide, sodium hydroxide, and ammonium hydroxide can be used as the base for this process.In the case of ammonium hydroxide , it is proposed that initial formation of an enamine is followed by an intramolecular SN2'reaction of the enamine carbon.For all other bases, the reaction most likely proceeds through a ketone enolate.Application of this novel cyclization has been extended to the synthesis of several 2,3-substituted, 2,3,5-trisubstituted, and 2,3,5,5-tetrasubstituted 2-cyclopenten-1-ones.

Synthesis of 2,3,5-trisubstituted-2-cyclopentenones via base induced cyclization of alpha-chloro unsaturated ketones

2,3,5-trisubstituted-2-cyclopentenones or 2,3-disubstituted-2-cyclopentenones (such as cis-jasmone) are prepared by contacting a 3-chloro-3,4-disubstituted-4-pentene-2-one with a strong base. Methods of preparing the reactants are also disclosed.