1579298-03-5

Basic information

• Product Name: 1-(1-(p-tolyl)vinyl)cyclobutan-1-ol
• Synonyms: 1-(1-(p-tolyl)vinyl)cyclobutan-1-ol
• CAS NO: 1579298-03-5
• Molecular Weight: 188.269
• Mol File: 1579298-03-5.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 1-(1-(p-tolyl)vinyl)cyclobutan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1-(p-tolyl)vinyl)cyclobutan-1-ol(1579298-03-5)
• EPA Substance Registry System: 1-(1-(p-tolyl)vinyl)cyclobutan-1-ol(1579298-03-5)

Safety Data

• Hazardous Substances Data: 1579298-03-5(Hazardous Substances Data)

Upstream product

• 1191-95-3 cyclobutanone 
• 51270-89-4 1-(1-bromoethenyl)-4-methylbenzene 
• 122-00-9 para-methylacetophenone 

Downstream Products

• 1579298-21-7 (S)-2-(chloromethyl)-2-(p-tolyl)cyclopentanone 
• 1599438-39-7 2-(4-fluorobenzyl)-2-p-tolylcyclopentanone 
• 99495-15-5 3-(p-tolyl)cyclohexan-1-one 

Relevant articles and documents

Electrochemical Semipinacol Rearrangements of Allylic Alcohols: Construction of All-Carbon Quaternary Stereocenters

The first examples of electrochemical trifluoromethylation and sulfonylation/semipinacol rearrangements of allylic alcohols were developed using cheap and stable RSO2Na (R = CF3, Ph) as reagents. Various β-trifluoromethyl and sulfonated ketones were obtained in moderate to excellent yields. This strategy provides a facile, direct, and complementary approach to construct all-carbon quaternary stereocenters. In addition, the reaction has the advantages of being chemical oxidant-free and metal-free and has safe and mild reaction conditions.

Lewis Base/Br?nsted Acid Co-catalyzed Enantioselective Sulfenylation/Semipinacol Rearrangement of Di- and Trisubstituted Allylic Alcohols

An enantioselective sulfenylation/semipinacol rearrangement of 1,1-disubstituted and trisubstituted allylic alcohols was accomplished with a chiral Lewis base and a chiral Br?nsted acid as cocatalysts, generating various β-arylthio ketones bearing an all-carbon quaternary center in moderate to excellent yields and excellent enantioselectivities. These chiral arylthio ketone products are common intermediates with many applications, for example, in the design of new chiral catalysts/ligands and the total synthesis of natural products. Computational studies (DFT calculations) were carried out to explain the enantioselectivity and the role of the chiral Br?nsted acid. Additionally, the synthetic utility of this method was exemplified by an enantioselective total synthesis of (?)-herbertene and a one-pot synthesis of a chiral sulfoxide and sulfone.

Electrophilic Trifluoromethylthiolation/Semipinacol Rearrangement: Preparation of β-SCF3 Carbonyl Compounds with α-Quaternary Carbon Center

A new and modular electrophilic trifluoromethylthiolation/semipinacol rearrangement of allylic silyl ethers has been developed under mild conditions. This approach allows the formation of a number of β-SCF3 carbonyl compounds with a cyclic and all-carbon quaternary center framework in moderate to good yields. It should be noted that this achievement is a metal-free process and just requires the use of simple acetyl chloride as an acidic promoter. Additionally, an interesting H-migration in competition with aryl-migration process was revealed.