90769-69-0

Basic information

• Product Name: Cyclohexene, 1,2,4-trimethyl-
• Synonyms: 1,2,4-trimethylcyclohex-1-ene;(+-)-1,2,4-trimethyl-cyclohexene;Cyclohexene,1,2,4-trimethyl;(+-)-1,2,4-Trimethyl-cyclohexen
• CAS NO: 90769-69-0
• Molecular Formula: C9H16
• Molecular Weight: 124.226
• Mol File: 90769-69-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 152 °C
• Density: 0.8275 g/cm3
• CAS DataBase Reference: Cyclohexene, 1,2,4-trimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexene, 1,2,4-trimethyl-(90769-69-0)
• EPA Substance Registry System: Cyclohexene, 1,2,4-trimethyl-(90769-69-0)

Safety Data

• Hazardous Substances Data: 90769-69-0(Hazardous Substances Data)

Upstream product

• 13702-58-4 3,4,6-trimethyl-3-cyclohexene-1-carbaldehyde 
• 95-63-6 1,2,4-Trimethylbenzene 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 103441-54-9 6-bromo-1,3,4-trimethyl-cyclohex-3-enecarboxylic acid 
• 18022-66-7 3,4-dimethylcyclohex-3-ene-1-carboxaldehyde 
• 72985-36-5 1,2,4-trimethyl-cyclohexa-1,4-diene 

Downstream Products

• 95-63-6 1,2,4-Trimethylbenzene 
• 922512-02-5 1-(3,4-dimethylphenyl)-1,3,4-trimethylcyclohexane 

Relevant articles and documents

Unsaturated aldehydes as alkene equivalents in the Diels-Alder reaction

A one-pot procedure is described for using α,β-unsaturated aldehydes as olefin equivalents in the Diels-Alder reaction. The method combines the normal electron demand cycloaddition with aldehyde dienophiles and the rhodium-catalyzed decarbonylation of aldehydes to afford cyclohexenes with no electron-with-drawing substituents. In this way, the aldehyde group serves as a traceless control element to direct the cycloaddition reaction. The Diels-Alder reactions are performed in a diglyme solution in the presence of a catalytic amount of boron trifluoride etherate. Subsequent quenching of the Lewis acid, addition of 0.3% of [Rh(dppp)2Cl] and heating to reflux achieves the ensuing decarbonylation to afford the product cyclohexenes. Under these conditions, acrolein, crotonaldehyde and cinnamaldehyde have been reacted with a variety of 1,3-dienes to afford cyclohexenes in overall yields between 53 and 88%. In these transformations, the three aldehydes serve as equivalents of ethylene, propylene and styrene, respectively.

Factors Influencing Conformational Preferences in Cyclohexenes

Conformational preferences have been measured for the first time for 4-substituted cyclohexenes in a solvent of low polarity.Measurements were made for the substituents Cl, Br, I, OH, OSiMe3, and CN and were compared with conformational preferences in cyclohexyl and exo-methylenecyclohex-3-yl.In the nearly nonpolar solvent CF2Cl2, in which intramolecular interactions are maximized, there is a much larger axial population for cyclohexen-4-yl than in cyclohexyl or exo-methylenecyclohex-3-yl.In particular, the dipolar interaction of the endocyclic double bond is reduced from that of the exocyclic double bond.This observation is confirmed by the almost negligible effect of symmetrizing the endocyclic double bond through 1,2-dimethyl substitution, in contrast with the large effect of symmetrizing the exocyclic double bond through 7,7-dimethyl substitution.Polar solvents increase the proportion of the axial conformer to a smaller extent for the endocyclic than for the exocyclic system, again in agreement with a lower dipolar effect in the endocyclic case.These results emphasize the anisotropic nature of the steric effects of double bonds.