164171-80-6

Basic information

• Product Name: 1-(4-methoxyphenyl)cyclobutan-1-ol
• Synonyms: 1-(4-methoxyphenyl)cyclobutan-1-ol
• CAS NO: 164171-80-6
• Molecular Weight: 178.231
• Mol File: 164171-80-6.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: 1-(4-methoxyphenyl)cyclobutan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-methoxyphenyl)cyclobutan-1-ol(164171-80-6)
• EPA Substance Registry System: 1-(4-methoxyphenyl)cyclobutan-1-ol(164171-80-6)

Safety Data

• Hazardous Substances Data: 164171-80-6(Hazardous Substances Data)

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 1191-95-3 cyclobutanone 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 215038-69-0 1-(4-methoxyphenyl)cyclobutyl acetate 

Downstream Products

• 77938-42-2 C₁₁H₁₃O⁽¹⁺⁾ 
• 215667-87-1 4-iodo-1-(4-methoxyphenyl)-1-butanone 
• 1283527-07-0 1-methoxy-4-(1-methylcyclobutyl)benzene 
• 56139-60-7 1-(4-Methoxyphenyl)-1,4-butandion 
• 1847-68-3 5-(4-methoxy-phenyl)-5-oxo-pentanoic acid methyl ester 

Relevant articles and documents

Studies on the Lithiation, Borylation, and 1,2-Metalate Rearrangement of O-Cycloalkyl 2,4,6-Triisopropylbenzoates

A broad range of acyclic primary and secondary 2,4,6-triisopropylbenzoate (TIB) esters have been used in lithiation-borylation reactions, but cyclic TIB esters have not. We have studied the use of cyclic TIB esters in lithiation-borylation reactions and looked at the effect of ring size (3- → 6-membered rings) on the three key steps of the lithiation-borylation protocol: deprotonation, borylation and 1,2-metalate rearrangement. Although all rings sizes could be deprotonated, the cyclohexyl case was impractically slow, and the cyclopentyl example underwent α-elimination faster than deprotonation at ?78 °C and so could not be used. Both cyclobutyl and cyclopropyl cases underwent rapid borylation, but only the cyclobutyl substrate underwent 1,2-metalate rearrangement. Thus, the cyclobutyl TIB ester occupies a “Goldilocks zone,” being small enough for deprotonation and large enough to enable 1,2-migration. The generality of the reaction was explored with a broad range of boronic esters.

Terminal Trifluoromethylation of Ketones via Selective C-C Cleavage of Cycloalkanols Enabled by Hypervalent Iodine Reagents

We report the first terminal trifluoromethylation at aryl and alkyl ketones' ?, or more remote sites via the selective C-C bond cleavage of cycloalkanols. The noncovalent interactions between alcohols and hypervalent iodines(III) reagents were disclosed to activate both alcohols and the Togni I reagent in the dual photoredox/copper catalysis for the transformation. This reaction was scalable to the gram-scale synthesis, applicable to the structurally complex steroid trifluoromethylation, and extendable to the pentafluoroethylation.

Regioselective Electrochemical Cyclobutanol Ring Expansion to 1-Tetralones

A mild electrochemical method for the regioselective preparation of 1-tetralones under environmentally friendly conditions from readily available cyclobutanols was developed. A series of aromatic- and heteroaromatic-fused 1-tetralones was accessed through ring expansion of the functionalized cyclobutanols via electrochemical generation of alkoxy radicals and intramolecular cyclization.