(+)-LIMONENE 1 2-EPOXIDE

Base Information

• Chemical Name: (+)-LIMONENE 1 2-EPOXIDE
• CAS No.: 203719-54-4
• Molecular Formula: C10H16O1
• Molecular Weight: 152.236
• Hs Code.: 2932999099
• Mol file: 203719-54-4.mol

Synonyms:(+)-p-mentha-1,8-diene 1,2-epoxide;7-Oxabicyclo[4.1.0]heptane,1-methyl-4-(1-methylethenyl)-,(4R)-(9CI);(+)-p-Mentha-1,8-diene 1,2-epoxide, (4R)-1,2-Epoxy-p-menth-8-ene, (4R)-4-Isopropenyl-1-methyl-1-cyclohexene 1,2-epoxide

Chemical Property of (+)-LIMONENE 1 2-EPOXIDE

Chemical Property:

• Refractive Index: n20/D 1.467
• Boiling Point: 198.1°Cat760mmHg
• Flash Point: 65.6°C
• PSA: 12.53000
• Density: 0.972g/cm³
• LogP: 2.60000
• Storage Temp.: 2-8°C
• Solubility.: Dichloromethane, Ether

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-Limonene1,2-epoxide(MixtureofDiastereomers) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Oxidized Limonene, a common reagent used in the preparation of fragrant compounds. (+)-LIMONENE 1 2-EPOXIDE, a common reagent used in the preparation of fragrant compounds. (+)-Limonene oxide (mixture of cis and trans) undergoes biocatalytic resolution in the presence of epoxide hydrolase to form enantiomerically pure cis- and trans-limonene oxides.

Technology Process of (+)-LIMONENE 1 2-EPOXIDE

There total 7 articles about (+)-LIMONENE 1 2-EPOXIDE 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: 95.0%

D-limonene (5989-27-5,555-08-8,8022-90-0,9003-73-0,95327-98-3) → (R)-8,9-limonene oxide (184488-93-5) + (1RS,2SR,4R)-limonene-1,2-epoxide (203719-54-4)

Guidance literature:

With 1H-imidazole; dihydrogen peroxide; sodium N-dodecanoyl-L-proplinate; Mn[5-(4-C₆H₄CO-(N-L-proline))-10,15,20-Ph₃-porphyrinyl]Cl; In ethanol; water; at 25 ℃; for 0.166667h; Further Variations:; Catalysts; Reagents; Product distribution;

DOI:10.1016/j.tetasy.2004.05.020

Reference yield: 90.0%

Limonene oxide (1195-92-2) → (1R,2R,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol (39904-09-1) + (1S,2S,4R)-limonene-1,2-diol (1946-00-5,13833-08-4,38630-75-0,39067-95-3,39903-99-6,39904-01-3,39904-04-6,39904-09-1,39904-12-6,57457-97-3,59121-74-3,59121-75-4,59121-76-5,59121-77-6,59121-82-3,76740-41-5) + (1RS,2SR,4R)-limonene-1,2-epoxide (203719-54-4)

Guidance literature:

Limonene oxide; With tris-buffer; mercury dichloride; at 20 ℃; for 2h;

With sodium tetrahydroborate; Further stages.;

DOI:10.1055/s-2007-966033

Reference yield: 58.0%

D-limonene (5989-27-5,555-08-8,8022-90-0,9003-73-0,95327-98-3) → (R)-8,9-limonene oxide (184488-93-5) + (1RS,2SR,4R)-limonene-1,2-epoxide (203719-54-4) + (R)-1-Methyl-4-(2-methyl-oxiranyl)-7-oxa-bicyclo[4.1.0]heptane

Guidance literature:

With Oxone; acetyl methyl β-cyclodextrin; sodium hydrogencarbonate; edetate disodium; In acetonitrile; at 20 ℃; for 0.333333h;

DOI:10.1021/jo034296d

upstream raw materials:

D-limonene

Limonene oxide

Downstream raw materials:

(1S,2S,4R)-limonene-1,2-diol

(1S,2R,4R)-limonene-1,2-epoxide

trans-p-menth-1-en-3-ol

cis-p-menth-1-en-3-ol

Refernces

An efficient and convenient synthesis of enantiopure 4-(t-butyldimethylsilyloxy)-cyclohex-2-en-1-one: A formal synthesis of (±)-mesembranol

10.1016/S0040-4039(01)00481-6

The research focuses on the efficient and convenient synthesis of enantiopure 4-(t-butyldimethylsilyloxy)-cyclohex-2-en-1-one (2a), a valuable chiral building block, and a formal synthesis of (±)-mesembranol (17). The purpose of the study was to develop an inexpensive and efficient route to 2a, leveraging the chiral vinyl triflate methodology. The key starting material was (+)-limonene oxide 1, which was converted through a series of reactions involving ozonolysis, Baeyer–Villiger oxidation, hydrolysis, and silylation to yield compound 4. Further reactions included regiospecific conversion of the epoxide mixture to allylic acetates, acylation, and elimination of acetate to yield diene 6. The synthesis concluded with oxidative cleavage and purification steps to obtain enone 2a, which was then used in the formal synthesis of (±)-mesembranol. The chemicals used in the process included (+)-limonene oxide, ozone, methanol, diisobutylaluminum-diisopropylamine, acetyl chloride, palladium catalysts, and various other reagents and solvents. The study concluded that the synthesis was high yielding and that the methodology could be readily scaled up for larger quantities, with a focus on avoiding chromatography and using distillation for purification.