24213-02-3

Basic information

• Product Name: ethyl 2-[2-(1,3-dioxolan-2-yl)ethyl]-3-oxobutanoate
• Synonyms: Ethyl 2-(2-(1,3-dioxolan-2-yl)ethyl)-3-oxobutanoate
• CAS NO: 24213-02-3
• Molecular Formula: C₁₁H₁₈O₅
• Molecular Weight: 230.2576
• Mol File: 24213-02-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 309°C at 760 mmHg
• Flash Point: 145.8°C
• Density: 1.104g/cm³
• Vapor Pressure: 0.000656mmHg at 25°C
• Refractive Index: 1.449
• CAS DataBase Reference: ethyl 2-[2-(1,3-dioxolan-2-yl)ethyl]-3-oxobutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-[2-(1,3-dioxolan-2-yl)ethyl]-3-oxobutanoate(24213-02-3)
• EPA Substance Registry System: ethyl 2-[2-(1,3-dioxolan-2-yl)ethyl]-3-oxobutanoate(24213-02-3)

Safety Data

• Hazardous Substances Data: 24213-02-3(Hazardous Substances Data)

Upstream product

• 18742-02-4 2-bromo-2-(2-ethyl)dioxolane 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 94007-49-5 4-Hydroxy-5-(2-<1,3-dioxolanyl-(2)>-ethyl)-6-methyl-pyrimidin 
• 505-03-3 5-oxohexanal 
• 94007-52-0 4-Hydroxy-2-mercapto-5-(2-<1,3-dioxolanyl-(2)>-ethyl)-6-methyl-pyrimidin 

Relevant articles and documents

X = Y - ZH Systems as Potential 1,3-Dipoles. Part 37. Generation of Nitrones from Oximes. Tandem Intramolecular 1,3-Azaprotio Cyclotransfer - Intramolecular 1,3-Dipolar Cycloaddition Reactions. Class 4 Processes.

Aldoximes and ketoximes containing two alkenyl moieties in different side chains undergo thermal conversion to 5- and 6-membered cyclic nitrones, via concerted 1,3-azaprotio cyclotransfer, followed by stereospecific intramolecular cycloaddition to give spiro- and fused-ring systems.An X-ray crystal structure of one such product is reported. Keywords: Nitrones, cycloaddition, intramolecular, oximes.

Intramolecular 1,3-dipolar cycloadditions of dihydroimidazolium ylides: Synthesis of pyrrolo[1,2,3-de]quinoxalines and imidazo[1,2-a]indoles

N-Alkylation of 4,5-dihydroimidazoles with alkene-containing bromomethyl ketones and treatment of the so-formed 4,5-dihydroimidazolium ions with DBU gives rise to an intramolecular 1,3-dipolar cycloaddition reaction that affords (via a reaction cascade involving eliminative ring-opening, recyclisation and prototropic tautomerism) unexpected hexahydropyrrolo[1,2,3-de]quinoxaline products. Steric bulk in both the dihydroimidazole and the dipolarophile allows isolation of an imidazo[1,2-a]indole, the initial product of cycloaddition. When the bromomethyl ketone contains no other functionality, or when cycloaddition is inhibited due to steric constraints, the dihydroimidazolium ion undergoes ring-opening hydrolysis followed by recyclization of the exposed amino ketone to afford either 3-alkyl-1-formylpiperazine-2-ones or 3-aryl-1-formyl-1,4,5,6- tetrahydropyrazines. The Royal Society of Chemistry 2006.

X = Y - ZH systems as potential 1,3-dipoles part 35. Generation of nitrones from oximes. Class 3 processes. Tandem intramolecular Michael addition (1,3-azaprotio cyclotransfer) - Intermolecular 1,3-dipolar cycloaddition reactions

Aldoximes and ketoximes possessing γ- or δ-alkenyl substituents undergo thermal conversion to 5-and 6- membered cyclic nitrones via a 1,3-azaprotio cyclotransfer, a 2n + 2oσ + 2π concerted process, rather than a Michael addition. The reactions can be performed as a tandem nitrone formation-cycloaddition sequence or, if required, the intermediate nitrones can be isolated. The cycloadditions usually proceed via an exo-transition state and show both regio- and diastereofacial-specificity. Preliminary attempts at chiral induction via a menthyl auxiliary are reported.