(R)-5-((1R)-menthyloxy)-2(5H)-furanone

Base Information

• Chemical Name: (R)-5-((1R)-menthyloxy)-2(5H)-furanone
• CAS No.: 77934-87-3
• Molecular Formula: C₁₄H₂₂O₃
• Molecular Weight: 238.327
• European Community (EC) Number: 632-840-4
• DSSTox Substance ID: DTXSID20601977
• Mol file: 77934-87-3.mol

Synonyms:77934-87-3;(R)-5-((1R)-menthyloxy)-2(5H)-furanone;SCHEMBL7000455;DTXSID20601977;URWJVUPZIGIVFZ-MLCFOIATSA-N;(5R)-5-{[(5R)-5-Methyl-2-(propan-2-yl)cyclohexyl]oxy}furan-2(5H)-one

Chemical Property of (R)-5-((1R)-menthyloxy)-2(5H)-furanone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 78-80 °C(lit.)
• Refractive Index: 1.492
• Boiling Point: 120-123 °C0.01 mm Hg(lit.)
• Flash Point: 153.456°C
• PSA: 35.53000
• Density: 1.045g/cm³
• LogP: 2.90290
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 238.15689456
• Heavy Atom Count: 17
• Complexity: 309

Purity/Quality:

98% ^*data from raw suppliers

(R)-5-[(1R)-MENTHYLOXY]-2(5H)-FURANONE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(C1)OC2C=CC(=O)O2)C(C)C
• Isomeric SMILES: C[C@@H]1CCC(C(C1)O[C@H]2C=CC(=O)O2)C(C)C

Technology Process of (R)-5-((1R)-menthyloxy)-2(5H)-furanone

There total 10 articles about (R)-5-((1R)-menthyloxy)-2(5H)-furanone 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: 61.0%

5-hydroxy-2-(5H)-furanone (14032-66-7) + (-)-menthol (2216-51-5) → (5R)-(L-menthyloxy)-2(5H)-furanone (112968-75-9,122079-41-8,122079-45-2,135041-07-5,77934-87-3) + (+)-(5S)-5-((+)-menthyl)oxy-2<5H>-furanone (112968-75-9)

Guidance literature:

at 100 ℃; for 20h; Yields of byproduct given;

DOI:10.1016/S0957-4166(00)80024-5

Reference yield: 23.0%

5-methoxyfuran-2(5H)-one (10449-66-8) + (-)-menthol (2216-51-5) → (5R)-(L-menthyloxy)-2(5H)-furanone (112968-75-9,122079-41-8,122079-45-2,135041-07-5,77934-87-3) + (+)-(5S)-5-((+)-menthyl)oxy-2<5H>-furanone (112968-75-9)

Guidance literature:

at 120 - 130 ℃; for 72h; Yields of byproduct given;

Reference yield: 18.0%

5-hydroxy-2-(5H)-furanone (14032-66-7) + (-)-menthol (2216-51-5) → (5R)-(L-menthyloxy)-2(5H)-furanone (112968-75-9,122079-41-8,122079-45-2,135041-07-5,77934-87-3)

Guidance literature:

With (1S)-(+)-10-camphorsulfonic acid; In benzene; for 10h; Reflux; Dean-Stark;

DOI:10.1246/bcsj.20190168

upstream raw materials:

5-hydroxy-2-(5H)-furanone

(-)-menthol

5-methoxyfuran-2(5H)-one

(+)-(5S)-5-((+)-menthyl)oxy-2<5H>-furanone

Downstream raw materials:

(4R,5R)-4-(1''-pyrrolidino)-5-((1'R,2'S,5'R)-menthyloxy)-butyrolactone

(4R,5R)-4-(1''-morpholino)-5-((1'R,2'S,5'R)-menthyloxy)-butyrolactone

(4R,5R)-5-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-4-((S)-1-phenyl-ethylamino)-dihydro-furan-2-one

(4S,5R)-5-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-4-((S)-1-phenyl-ethylamino)-dihydro-furan-2-one