2-Cyclopenten-1-one, 3,4-dimethyl-4-(4-methylphenyl)-, (R)-

Base Information

• Chemical Name: 2-Cyclopenten-1-one, 3,4-dimethyl-4-(4-methylphenyl)-, (R)-
• CAS No.: 109334-10-3
• Molecular Formula: C14H16O
• Molecular Weight: 200.28
• Mol file: 109334-10-3.mol

Synonyms:

Chemical Property of 2-Cyclopenten-1-one, 3,4-dimethyl-4-(4-methylphenyl)-, (R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Cyclopenten-1-one, 3,4-dimethyl-4-(4-methylphenyl)-, (R)-

There total 28 articles about 2-Cyclopenten-1-one, 3,4-dimethyl-4-(4-methylphenyl)-, (R)- 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: 91.0%

(2R,3S,4R)-3,4-Dimethyl-2-phenylselanyl-4-p-tolyl-cyclopentanone (183275-46-9) → (4R)-3,4-dimethyl-4-(p-tolyl)-2-cyclopentenone (109334-10-3)

Guidance literature:

With dihydrogen peroxide; acetic acid; for 1h; Ambient temperature;

DOI:10.1021/jo961190s

Reference yield:

C14H18O → (4R)-3,4-dimethyl-4-(p-tolyl)-2-cyclopentenone (109334-10-3)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.tet.2016.12.072

Reference yield:

1-(3-chloroprop-1-en-2-yl)-4-methylbenzene (40089-09-6) → (4R)-3,4-dimethyl-4-(p-tolyl)-2-cyclopentenone (109334-10-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / NaH / tetrahydrofuran

2: 75 percent / potassium tert-butoxide / dimethylsulfoxide / 65 °C

3: diethyl ether / 20 °C

4: diethyl ether; methanol / Ambient temperature

5: chromous perchlorate / H₂O; acetone / 0 °C

6: 2.) Li₂CO₃, LiBr / 1.) ether, -78 deg C, 2.) DMF, 80 deg C

With chromium(III) perchlorate; potassium tert-butylate; lithium carbonate; sodium hydride; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; water; dimethyl sulfoxide; acetone;

DOI:10.1021/ja00249a066

upstream raw materials:

methyllithium

(S)-(+)-5-methyl-5-(4-methylphenyl)cyclopent-2-en-1-one

(1RS,5S)-1,4-dimethyl-5-p-tolyl-2-cyclopenten-1-ol

(2R,3S,4R)-3,4-Dimethyl-2-phenylselanyl-4-p-tolyl-cyclopentanone

Downstream raw materials:

(S)-(+)-β-cuparenone

(R)-(+)-β-cuparenone

Refernces

• 1、 Castro, Jaume,Moyano, Albert,Pericas, Miquel A.,Riera, Antoni,Greene, Andrew E.,Alvarez-Larena, Angel,Piniella, Joan F.. "Asymmetric approach to (+)-β-cuparenone by intramolecular Pauson-Khand reaction". . p. 9016 - 9020. Retrieved 2007/10/03.
• 2、 Asaoka, Morio,Hayashibe, Satoshi,Sonoda, Syuzo,Takei, Hisashi. "SYNTHESIS AND UTILIZATION OF OPTICALLY ACTIVE 2-SUBSTITUTED 4-(TRIMETHYLSILYL)CYCLOPENTANONES: SYNTHESIS OF (-)-MASSOIALACTONE AND (+)-β-CUPARENONE". . p. 4761 - 4764. Retrieved 2007/10/02.