20614-90-8

Basic information

• Product Name: 3-tert-butyl-cyclobutanone
• Synonyms: 3-tert-butyl-cyclobutanone;3-tert-butylcyclobutan-1-one;Cyclobutanone, 3-(1,1-dimethylethyl)-
• CAS NO: 20614-90-8
• Molecular Formula: C₈H₁₄O
• Molecular Weight: 126.19616
• Mol File: 20614-90-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-tert-butyl-cyclobutanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-tert-butyl-cyclobutanone(20614-90-8)
• EPA Substance Registry System: 3-tert-butyl-cyclobutanone(20614-90-8)

Safety Data

• Hazardous Substances Data: 20614-90-8(Hazardous Substances Data)

Upstream product

• 558-37-2 tert-butylethylene 
• 76-02-8 trifluoroacetyl chloride 
• 182755-64-2 3-tert-butyl-2,2-dichlorocyclobutanone 
• 20476-25-9 3-t-Butyl-cyclobutanol-⁽¹⁾ 
• 186581-53-3 diazomethane 
• 59005-31-1 tert-Butylketen 
• 201230-82-2 carbon monoxide 
• 558-17-8 tert-Butyl iodide 
• 106-95-6 allyl bromide 

Downstream Products

• 13294-73-0 1-tert-butyl-4-methylenecyclohexane 
• 5581-94-2 3-tert-Butyl-cyclopentanone 
• 107912-94-7 trans-2-tert.-Butyl-cyclopropan-carbonsaeure-(1)-amid 
• 1019842-37-5 1-(1-benzyloxy-propa-1,2-dienyl)-3-tert-butyl-cyclobutanol 

Relevant articles and documents

Desymmetrization of Prochiral Cyclobutanones via Nitrogen Insertion: A Concise Route to Chiral γ-Lactams

Asymmetric access to γ-lactams is achieved via a cyclobutanone ring expansion using widely available (1S,2R)-1-amino-2-indanol for chiral induction. Mechanistic analysis of the key N,O-ketal rearrangement reveals a Curtin–Hammett scenario, which enables a downstream stereoinduction (up to 88:12 dr) and is corroborated by spectroscopic, crystallographic, and computational studies. In combination with an easy deprotection protocol, this operationally simple sequence allows the synthesis of a range of optically pure γ-lactams, including those bearing all-carbon quaternary stereocenters. In addition, the formal synthesis of drug molecules baclofen, brivaracetam, and pregabalin further demonstrates the synthetic utility and highlights the general applicability of the presented method.

Palladium-catalyzed, asymmetric Baeyer-Villiger oxidation of prochiral cyclobutanones with PHOX ligands

Described in this report is a general method for the conversion of prochiral 3-substituted cyclobutanones to enantioenriched γ-lactones through a palladium-catalyzed Baeyer-Villiger oxidation using phosphinooxazoline ligands in up to 99% yield and 81% ee. Lactones of enantiopurity ≥93% could be obtained through a single recrystallization step. Importantly, 3,3-disubtituted cyclobutanones produced enantioenriched lactones containing a β-quaternary center.

3-(2-Acylamino-1-Hydroxyethyl)-Morpholine Derivatives and Their Use as Bace Inhibitors

The present invention provides BACE inhibitors of Formula (I); methods for their use and preparation, and intermediates useful for their preparation.