[(3R)-4,4-dimethyl-2-oxooxolan-3-yl] prop-2-enoate

Base Information

• Chemical Name: [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] prop-2-enoate
• CAS No.: 102096-60-6
• Molecular Formula: C9H12 O4
• Molecular Weight: 184.192
• Hs Code.: 2932209090
• European Community (EC) Number: 625-652-9
• DSSTox Substance ID: DTXSID50383517
• Nikkaji Number: J677.683C
• Wikidata: Q76149061
• Mol file: 102096-60-6.mol

Synonyms:102096-60-6;[(3R)-4,4-dimethyl-2-oxooxolan-3-yl] prop-2-enoate;(R)-4,4-Dimethyl-2-oxotetrahydrofuran-3-yl acrylate;(3R)-4,4-Dimethyl-2-oxooxolan-3-yl prop-2-enoate;(R)-(+)-ALPHA-ACRYLOYLOXY-BETA,BETA-DIMETHYL-GAMMA-BUTYROLACTONE;( poundO)-(+)-Alpha-acryloyloxy-beta,beta-dimethyl-gamma-butyrolactone;SCHEMBL1351991;DTXSID50383517;MFCD00043403;AKOS015913251;F53060;(R)-a-acryloyloxy-b,b-dimethyl-gamma-butyrolactone;(R)-4,4-Dimethyl-2-oxotetrahydrofuran-3-ylacrylate;(R)-4,4-Dimethyl-3-(acryloyloxy)-4,5-dihydrofuran-2(3H)-one;(R)-alpha-Acryloyloxy-beta,beta-dimethyl-gamma-butyrolactone, 95%;(R)- alpha -Acryloyloxy- beta , beta -dimethyl- gamma -butyrolactone

Chemical Property of [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] prop-2-enoate

Chemical Property:

• Vapor Pressure: 0.000648mmHg at 25°C
• Melting Point: 7-8 °C(lit.)
• Refractive Index: n20/D 1.46(lit.)
• Boiling Point: 84 °C0.1 mm Hg(lit.)
• Flash Point: 130.4°C
• PSA: 52.60000
• Density: 1.14g/cm³
• LogP: 0.66720
• Storage Temp.: 2-8°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 184.07355886
• Heavy Atom Count: 13
• Complexity: 254

Purity/Quality:

99% ^*data from raw suppliers

(R)-α-Acryloyloxy-β,β-dimethyl-γ-butyrolactone 95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,N
• Statements: 36/37/38-51/53
• Safety Statements: 26-28-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(COC(=O)C1OC(=O)C=C)C
• Isomeric SMILES: CC1(COC(=O)[C@@H]1OC(=O)C=C)C

Technology Process of [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] prop-2-enoate

There total 3 articles about [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] prop-2-enoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

acryloyl chloride (814-68-6,25189-84-8) + (R)-Pantolacton (599-04-2) → (R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl acrylate (102096-60-6)

Guidance literature:

With hydrogenchloride; triethylamine; In dichloromethane;

Reference yield: 57.0%

acryloyl chloride (814-68-6,25189-84-8) + (S)-pantolactone (79-50-5,599-04-2,5405-40-3,52126-90-6) → (R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl acrylate (102096-60-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -10 ℃; for 2h;

Reference yield:

pantolactone (79-50-5) → (R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl acrylate (102096-60-6)

Guidance literature:

Multi-step reaction with 2 steps

1: lipase from Candida cylindracea (Altus 20) / various solvent(s) / 8 h / 20 °C

2: 74 percent / Et₃N / CH₂Cl₂ / 5 h / -24 °C

With lipase from Candida cylindracea (Altus 20); triethylamine; In dichloromethane; 1: Acylation / 2: Acetylation;

DOI:10.1016/S0957-4166(00)00130-0

upstream raw materials:

acryloyl chloride

(R)-Pantolacton

pantolactone

(S)-pantolactone

Downstream raw materials:

(R)-2-<(S)-4-methyl-3-cyclohexene-1-carboxy>-3,3-dimethyl-γ-butyrolactone

(1S)-3-cyclohexenecarboxylic acid

(S)-Cyclohex-3-enecarboxylic acid 4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester

3-Cyclohexene-1-carboxylic acid (R)-pentalactone ester