102096-60-6

Basic information

• Product Name: (R)-(+)-ALPHA-ACRYLOYLOXY-BETA,BETA-DIMETHYL-GAMMA-BUTYROLACTONE
• Synonyms: (R)-(+)-ALPHA-ACRYLOYLOXY-BETA,BETA-DIMETHYL-GAMMA-BUTYROLACTONE;(R)-ALPHA-ACRYLOYLOXY-BETA,BETA-DIMETHYL-GAMMA-BUTYROLACTONE;(R)-a-Acryloyloxy-b,b-dimethyl-g-butyrolactone;(R)-ALPHA-ACRYLOXY-BETA BETA-DIM.-GAMMA&;(r)-α-acryloyloxy-β,β-dimethyl-γ-butyrolactone;ALPHA-ACRYLOYLOXY-BETA,BETA-DIMETHYL-GAMMA-BUTYROLACTONE;[(3R)-4,4-DIMETHYL-2-OXOOXOLAN-3-YL] PROP-2-ENOATE
• CAS NO: 102096-60-6
• Molecular Formula: C₉H₁₂O₄
• Molecular Weight: 184.19
• Product Categories: Chiral Building Blocks;Lactones;Organic Building Blocks
• Mol File: 102096-60-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 7-8 °C(lit.)
• Boiling Point: 84 °C0.1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.125 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.000648mmHg at 25°C
• Refractive Index: n20/D 1.46(lit.)
• Storage Temp.: 2-8°C
• BRN: 4668587
• CAS DataBase Reference: (R)-(+)-ALPHA-ACRYLOYLOXY-BETA,BETA-DIMETHYL-GAMMA-BUTYROLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-ALPHA-ACRYLOYLOXY-BETA,BETA-DIMETHYL-GAMMA-BUTYROLACTONE(102096-60-6)
• EPA Substance Registry System: (R)-(+)-ALPHA-ACRYLOYLOXY-BETA,BETA-DIMETHYL-GAMMA-BUTYROLACTONE(102096-60-6)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-51/53
• Safety Statements: 26-28-61
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 3
• F: 8
• Hazardous Substances Data: 102096-60-6(Hazardous Substances Data)

Usage

General Description

(R)-(+)-ALPHA-ACRYLOYLOXY-BETA,BETA-DIMETHYL-GAMMA-BUTYROLACTONE is a chemical compound that is commonly used as a monomer in the production of various polymer materials. It is a lactone with a butyrolactone structure and a beta,beta-dimethyl substitution, and an alpha-acryloyloxy group. This chemical has applications in the production of polymers with specific physical and chemical properties, and it can also be used as a reagent in organic synthesis. Additionally, it is known to have potential medical and pharmaceutical applications due to its unique structure and properties. However, it is important to handle this compound with care and in compliance with safety regulations due to its potential hazards.

InChI:InChI=1/C9H12O4/c1-4-6(10)13-7-8(11)12-5-9(7,2)3/h4,7H,1,5H2,2-3H3/t7-/m0/s1

Upstream product

• 814-68-6 acryloyl chloride 
• 79-50-5 (S)-pantolactone 
• 599-04-2 (R)-Pantolacton 
• 79-50-5 pantolactone 

Downstream Products

• 144193-86-2 O-((1S)-1-methylbicyclo<2.2.1>hept-5-ene-2-endo-carbonyl)-D-pantolactone 
• 144193-88-4 O-((1R)-1-methylbicyclo<2.2.1>hept-5-ene-2-endo-carbonyl)-D-pantolactone 
• 115219-34-6 (1S,2R,4R,7S)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester 
• 115219-34-6 (1R,2S,4S,7R)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester 
• 102096-64-0 3-Cyclohexene-1-carboxylic acid (R)-pentalactone ester 
• 102096-64-0 (S)-Cyclohex-3-enecarboxylic acid 4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester 
• 102096-63-9 (R)-2-<(S)-4-methyl-3-cyclohexene-1-carboxy>-3,3-dimethyl-γ-butyrolactone 
• 5708-19-0 (1S)-3-cyclohexenecarboxylic acid 

Relevant articles and documents

DIASTEREOFACE-DISCRIMINATIVE METAL COORDINATION IN ASYMMETRIC SYNTHESIS: D-PANTOLACETONE AS PRACTICAL CHIRAL AUXILIARY FOR LEWIS ACID CATALYZED DIELS-ALDER REACTIONS

TiCl4-catalyzed Diels-Alder additions of the acrylate of commercial D-pantoloacetone to cyclopentadiene, isoprene and butadiene proceed with very high diastereofacial selectivity.Practical and mechanistic aspects of these reactions are discussed.

Discovery of GS-9669, a thumb site II non-nucleoside inhibitor of NS5B for the treatment of genotype 1 chronic hepatitis C infection

Investigation of thiophene-2-carboxylic acid HCV NS5B site II inhibitors, guided by measurement of cell culture medium binding, revealed the structure-activity relationships for intrinsic cellular potency. The pharmacokinetic profile was enhanced through incorporation of heterocyclic ethers on the N-alkyl substituent. Hydroxyl groups were incorporated to modulate protein binding. Intrinsic potency was further improved through enantiospecific introduction of an olefin in the N-acyl motif, resulting in the discovery of the phase 2 clinical candidate GS-9669. The unexpected activity of this compound against the clinically relevant NS5B M423T mutant, relative to the wild type, was shown to arise from both the N-alkyl substituent and the N-acyl group.

Enzymatic kinetic resolution of pantolactone: Relevance to chiral auxiliary chemistry

Racemic pantolactone was converted into either enantiomerically enriched pantolactone acetate or pantolactone acrylate by an enzyme-catalysed kinetic resolution process. Pantolactone is known to be a good auxiliary for acrylate in the Diels-Alder reaction. (C) 2000 Elsevier Science Ltd.