(R)-6-Methyl-5,6-dihydro-2H-pyran-2-one

Base Information

• Chemical Name: (R)-6-Methyl-5,6-dihydro-2H-pyran-2-one
• CAS No.: 119067-60-6
• Molecular Formula: C6H8O2
• Molecular Weight: 112.128
• UNII: CP9AFD9NRZ
• Nikkaji Number: J1.219.410B
• Mol file: 119067-60-6.mol

Synonyms:119067-60-6;(6R)-6-methyl-5,6-dihydro-2H-pyran-2-one;2H-Pyran-2-one, 5,6-dihydro-6-methyl-, (6R)-;CP9AFD9NRZ;R-(-)-Parasorbic acid;Parasorbic acid, (-)-;(R)-6-Methyl-5,6-dihydro-2H-pyran-2-one;SCHEMBL23713367;(6R)-5,6-Dihydro-6-methyl-2H-pyran-2-one;EN300-26869118

Chemical Property of (R)-6-Methyl-5,6-dihydro-2H-pyran-2-one

Chemical Property:

• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 112.052429494
• Heavy Atom Count: 8
• Complexity: 127

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC=CC(=O)O1
• Isomeric SMILES: C[C@@H]1CC=CC(=O)O1

Technology Process of (R)-6-Methyl-5,6-dihydro-2H-pyran-2-one

There total 29 articles about (R)-6-Methyl-5,6-dihydro-2H-pyran-2-one 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: 99.0%

(-)-6-(6R)-methyldihydropyr-4-en-2-one (118992-11-3) → (6R)-6-methyl-5,6-dihydro-2H-pyran-2-one (119067-60-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In chloroform; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)86648-5

Reference yield: 89.0%

(R)-pent-4-en-2-yl acrylate (263238-26-2) → (6R)-6-methyl-5,6-dihydro-2H-pyran-2-one (119067-60-6)

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 8h; Inert atmosphere; Reflux;

DOI:10.1039/c3ra44478c

Reference yield: 57.0%

acetic acid tert-butyl ester (540-88-5) + Methyl (R)-3-hydroxybutyrate (3976-69-0) → (6R)-6-methyl-5,6-dihydro-2H-pyran-2-one (119067-60-6)

Guidance literature:

acetic acid tert-butyl ester; Methyl (R)-3-hydroxybutyrate; With n-butyllithium; In tetrahydrofuran; at -78 ℃;

With sodium tetrahydroborate; In ethanol;

With toluene-4-sulfonic acid; In toluene; Reflux;

DOI:10.1021/ol301743t DOI:10.1021/ol301743t

upstream raw materials:

3,5-dioxohexanoic acid methyl ester

methyl 3,5-dihydroxyhexanoate

(4R,6R)-4-hydroxy-6-methyltetrahydro-2H-pyran-2-one

(4R,6S)-4-hydroxy-6-methyltetrahydropyran-2-one

Downstream raw materials:

(4R,6R)-6-Methyl-4-phenyl-tetrahydro-pyran-2-one

botryolide B

Refernces

• 1、 Mohapatra, Debendra K.,Umamaheshwar, Gonela,Rao, M. Mallikarjuna,Umadevi, Deivasigamani,Yadav, Jhillu S.. "Concise total synthesis of botryolide B". . p. 8335 - 8340. Retrieved 2014/02/14.
• 2、 Bartlett, Sean,Boese, Dietrich,Ghori, Daniel,Mechsner, Bastian,Pietruszka, Joerg. "Enantiomerically pure allylboronic esters as versatile reagents in the enantioselective synthesis of dihydro-α-pyrone-containing natural products". . p. 1106 - 1114. Retrieved 2013/05/21.