199383-82-9

Basic information

• Product Name: 1-Cyclohexen-1-ol, 4-phenyl-, acetate
• CAS NO: 199383-82-9
• Molecular Formula: C14H16O2
• Molecular Weight: 216.28
• Mol File: 199383-82-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-Cyclohexen-1-ol, 4-phenyl-, acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclohexen-1-ol, 4-phenyl-, acetate(199383-82-9)
• EPA Substance Registry System: 1-Cyclohexen-1-ol, 4-phenyl-, acetate(199383-82-9)

Safety Data

• Hazardous Substances Data: 199383-82-9(Hazardous Substances Data)

Upstream product

• 108-22-5 Isopropenyl acetate 
• 5769-13-1 4-phenyl-cyclohexanol 
• 4894-75-1 1-phenyl-4-cyclohexanone 
• 64-19-7 acetic acid 
• 10534-59-5 tetrabutylammonium acetate 

Downstream Products

• 4894-75-1 1-phenyl-4-cyclohexanone 

Relevant articles and documents

X-ray structure and conformation of some enol acetates derived from simple ketones

The conformational arrangements of a series of enol acetates derived from simple ketones have been examined by X-ray crystallography. For this series, the carbonyl enol motif was found to adopt a similar conformation.

Elimination-addition mechanism for nucleophilic substitution reaction of cyclohexenyl iodonium salts and regioselectivity of nucleophilic addition to the cyclohexyne intermediate

The reaction of 4-substituted cyclohex-1-enyl(phenyl)iodonium tetrafluoroborate with tetrabutyl-ammonium acetate gives both the ipso and cine acetate-substitution products in aprotic solvents. The isomeric 5-substituted iodonium salt also gives the same mixture of the isomeric acetate products. The reaction is best explained by an elimination-addition mechanism with 4-substituted cyclohexyne as a common intermediate. The cyclohexyne formation was confirmed by deuterium labeling and trapping to lead to [4 + 2] cycloadducts and a platinum-cyclohexyne complex. Cyclohexyne can also be generated in the presence of some other mild bases such as fluoride ion, alkoxides, and amines, though amines are less effective bases for the elimination. Kinetic deuterium isotope effects show that the anionic bases induce the E2 elimination (k H/kD > 2), while the amines allow formation of a cyclohexenyl cation in chloroform to lead to E1 as well as SN1 reactions (k H/kD ≈ 1). Bases are much less effective in methanol, and methoxide was the only base to efficiently afford the cyclohexyne intermediate. Nucleophiles react with the cyclohexyne to give regioisomeric products in the ratio dependent on the ring substituent. The observed regioselectivity of nucleophilic addition to substituted cyclohexynes is rationalized from calculated LUMO populations, which are governed by the bond angles at the acetylenic carbons: The less deformed carbon has a higher LUMO population and is preferentially attacked by the nucleophile.