2292-84-4

Basic information

• Product Name: 3-Ethoxy-2,2-diMethylcyclobutanone
• Synonyms: 3-Ethoxy-2,2-diMethylcyclobutanone;3-Ethoxy-2,2-dimethylcyclobutanone - E6179
• CAS NO: 2292-84-4
• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.19556
• Mol File: 2292-84-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Ethoxy-2,2-diMethylcyclobutanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Ethoxy-2,2-diMethylcyclobutanone(2292-84-4)
• EPA Substance Registry System: 3-Ethoxy-2,2-diMethylcyclobutanone(2292-84-4)

Safety Data

• Hazardous Substances Data: 2292-84-4(Hazardous Substances Data)

Upstream product

• 598-26-5 dimethylketene 
• 109-92-2 ethyl vinyl ether 
• 79-30-1 isobutyryl chloride 
• 4313-48-8 3-ethoxy-4,4-dimethylcyclobut-2-en-1-one 

Downstream Products

• 1434247-99-0 3-amino-2,2-dimethylcyclobutanol 

Relevant articles and documents

Carbanionic Rearrangements of (Halomethylene)cycloalkanes

The mechanism for the unusual base-induced ring-enlargement reaction of (halomethylene)cyclobutanes to 1-halocyclopentenes was examined by C-13 labeling studies with (bromomethylene)cyclobutane (1), cis- and trans-1-(bromomethylene)-3-ethoxy-2,2-dimethylcyclobutane (15 and 16), and 1-(bromomethylene)-2,2,4,4-tetramethylcyclobutane (22).Two competing processes were found to lead from the vinyl anion to rearranged products: (1) rehybridization of the vinyl anion to a 1,2-carbene-anion, which subsequently undergoes rearrangement, and (2) a Beckmann-like simultaneousmigration of bromide and ring carbon.Both processes subtly bypass the "forbidden" alkyl-to-carbanion shift.

An efficient procedure for preparation of 2-monoalkyl or 2-monoaryl-3-ethoxycyclobutanones

Optimized reaction conditions for the preparation of various 2-monosubstituted 3-ethoxycyclobutanones are described. 2-Monoalkyl 3-ethoxycyclobutanones were efficiently prepared by the reaction of the corresponding carboxylic acid chlorides and an excess amount of ethyl vinyl ether in the presence of diisopropylethylamine at 90 °C in a sealed tube. 2-Monoaryl 3-ethoxycyclobutanones were prepared by using 2,6-lutidine as a base in the above-mentioned procedure.

Discovery of the Selective Protein Kinase C-θ Kinase Inhibitor, CC-90005

The PKC-θ isoform of protein kinase C is selectively expressed in T lymphocytes and plays an important role in the T cell antigen receptor (TCR)-triggered activation of mature T cells, T cell proliferation, and the subsequent release of cytokines such as

Lewis-acid Promoted Chemoselective Condensation of 2-Aminobenzimidazoles or 3-Aminoindazoles with 3-Ethoxycyclobutanones to Construct Fused Nitrogen heterocycles

A Lewis-acid promoted chemoselective condensation of 2-aminobenzimidazoles or 3-aminoindazoles with 3-ethoxycyclobutanones is presented. Diverse fused heterocycles benzo[4,5]-imidazo[1,2-a]pyrimidine and pyrimido[1,2-b]-indazole derivatives were obtained in moderate to high yields under mild conditions, the reaction mechanism of which was in sharp contrast to previous [3+3] annulation reaction of 3-ethoxycyclobutanones. (Figure presented.).

Lewis Acid-Mediated [3+3] Annulation for the Construction of Substituted Pyrimidine and Pyridine Derivatives

A direct and single-step procedure towards substituted pyrimidine and pyridine derivatives via Lewis acid-promoted [3+3] annulation between 3-ethoxycyclobutanones and enamines or amidines is presented. Diverse substituted pyrimidine and pyridine derivatives were obtained in good to high yields with a wide substrate scope. (Figure presented.).

Phosphothreonine as a Catalytic Residue in Peptide-Mediated Asymmetric Transfer Hydrogenations of 8-Aminoquinolines

Phosphothreonine (pThr) was found to constitute a new class of chiral phosphoric acid (CPA) catalyst upon insertion into peptides. To demonstrate the potential of these phosphopeptides as asymmetric catalysts, enantioselective transfer hydrogenations of a previously underexplored substrate class for CPA-catalyzed reductions were carried out. pThr-containing peptides lead to the observation of enantioselectivities of up to 94:6 e.r. with 2-substituted quinolines containing C8-amino functionality. NMR studies indicate that hydrogen-bonding interactions promote strong complexation between substrates and a rigid β-turn catalyst.