10359-02-1

Basic information

• Product Name: beta-Isopropyl-beta-propiolactone
• Synonyms: beta-Isopropyl-beta-propiolactone
• CAS NO: 10359-02-1
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• Mol File: 10359-02-1.mol

Chemical Properties

• Boiling Point: 163.8°Cat760mmHg
• Flash Point: 51.8°C
• Appearance: /
• Density: 1.031g/cm³
• Vapor Pressure: 2.03mmHg at 25°C
• Refractive Index: 1.444
• CAS DataBase Reference: beta-Isopropyl-beta-propiolactone(CAS DataBase Reference)
• NIST Chemistry Reference: beta-Isopropyl-beta-propiolactone(10359-02-1)
• EPA Substance Registry System: beta-Isopropyl-beta-propiolactone(10359-02-1)

Safety Data

• Hazardous Substances Data: 10359-02-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H10O2/c1-4(2)5-3-8-6(5)7/h4-5H,3H2,1-2H3

Upstream product

• 463-51-4 Ketene 
• 78-84-2 isobutyraldehyde 

Downstream Products

• 646-07-1 4-Methylpentanoic acid 
• 126442-54-4 benzyl (S)-3-hydroxy-4-methylpentanoate 
• 170715-33-0 (S)-4-(1-methylethyl)oxetan-2-one 

Relevant articles and documents

Asymmetric synthesis of tetrahydrolipstatin and valilactone

The highly diastereoselective aldol reaction between acyl complexes of the iron chiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)] and β-hydroxy aldehydes (obtained via a Noyori asymmetric hydrogenation), followed by a tandem oxidative decomplexation-cyclisation process gives access to β-substituted and α,β-disubstituted β-lactones in high ee. This methodology has been employed in the asymmetric syntheses of tetrahydrolipstatin and valilactone.

Lipase promoted asymmetric trans-esterification of 4-alkyl-, 3-alkyl- and 3,4-dialkyloxetan-2-ones with ring-opening

Kinetic resolution of(+/-)-4-substituted [(+/-)-1], 3-substituted [(+/-)-4] and 3,4-disubstituted oxetan-2-ones [(+/-)-7] was effected by the action of lipases in organic solvents. The substrates (+/-)-1, (+/-)-4 and (+/-)-7 were prepared by [2 + 2] cycloaddition of aldehydes with ketene, intramolecular substitution of 3-bromoalkanoic acids and the Adam's cyclization of anti- and syn-3-hydroxyalkanoic acids, respectively. Lipase PS exhibited good activity towards all the oxetanones and was employed for the resolution experiments except with (+/-)-4-methyloxetan-2-one (+/-)-1a for which PPL was used. The stereoselectivity was satisfactory for obtaining oxetan-2-ones of high ee's except for a few cases. The configuration of new compounds was established by chemical correlation and CD spectroscopy.

Cationic palladium(II) complex-catalyzed [2 + 2] cycloaddition and tandem cycloaddition-allylic rearrangement of ketene with aldehydes: An improved synthesis of sorbic acid

Cationic palladium(II) complexes [PdL2(PhCN)2](BF4)2 efficiently catalyze the [2 + 2] cycloaddition of ketene with aldehydes to give the corresponding oxetan-2-ones, among which 4-vinyl-substituted ones are further isomerized under the conditions to give 3,6-dihydro-2H-pyran-2-ones in good yields.

Process for producing a β-lactone derivative

The present invention provides a process for producing a β-lactone derivative by reacting an aldehyde represented by formula (1): wherein R represents a C1-C15 alkyl group which may be substituted by an aryl group, a C2-C15 alkenyl group, a 5-7-membered a

Asymmetric Cycloaddition of Ketene with Aldehydes catalysed by Chiral Bissulfonamide-Trialkylaluminium Complexes

Asymmetric cycloaddition of ketene with the aldehydes 1a-g, catalysed by 10 molpercent of C2-symmetric bissulfonamide 2a-c-R3Al complexes afforded optically active 4-substituted oxetan-2-ones 3a-g in up to 74percent enantiomeric excess.