112698-16-5

Basic information

• Product Name: 3-Cyclohexene-1-carboxaldehyde, 3-acetyl- (9CI)
• Synonyms: 3-Cyclohexene-1-carboxaldehyde, 3-acetyl- (9CI)
• CAS NO: 112698-16-5
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19038
• Product Categories: ACETYLGROUP
• Mol File: 112698-16-5.mol

Chemical Properties

• Boiling Point: 264.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.122±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 3-Cyclohexene-1-carboxaldehyde, 3-acetyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyclohexene-1-carboxaldehyde, 3-acetyl- (9CI)(112698-16-5)
• EPA Substance Registry System: 3-Cyclohexene-1-carboxaldehyde, 3-acetyl- (9CI)(112698-16-5)

Safety Data

• Hazardous Substances Data: 112698-16-5(Hazardous Substances Data)

Upstream product

• 112698-08-5 4-(2,6-dimethoxytetrahydropyran-3-yl)butan-2-one 

Relevant articles and documents

2-Alkoxy-3-oxoalkyl-tetrahydropyrans and -tetrahydrofurans: versatile intermediates in heterocyclic synthesis

A new Lewis acid-catalysed Michael-type addition of heterocyclic enol ethers to hemiacetal vinylogues 1 or to enones in the presence of a hydroxylic compounds is described.The 1,5-keto acetal 3 so obtained have been studied with a view to synthetic applications.Acidic hydrolysis of compound 3 leads in most cases to annulation products 9 in a stereocontrolled manner.Organometallic addition, hydride reduction or reductive amination of 1,5-keto acetals 3 afford, in good yields, the hydroxy acetals 12 (and cyclisation products 13) and amino acetals 18, respectively.Acidic treatment of these compounds gave access to oxa- and aza-annulation products 13, 17 and 19 by an efficient kinetically controlled heterocyclisation process.These products can be obtained with high cis-junction selectivities as established by NMR spectroscopy and confirmed by equilibration studies.

REACTION DES VINYLOGUES D'HEMIACETALS ET DE LEURS EQUIVALENTS SYNTHETIQUES SUR LES ETHERS D'ENOLS HETEROCYCLIQUES

We describe the reaction of hemiacetal vinylogs 2 or their synthetic equivalent with cyclic enol ethers 1 yielding ketoacetals 3.Acidic treatment of these compounds leads to bicyclic heterocycles 8 or enone aldehyde 12 depending on the nature of substituents R1.