(6R)-[(1R)-1,5-dimethylhex-4-enyl]-3-methylcyclohex-2-en-1-one

Base Information

• Chemical Name: (6R)-[(1R)-1,5-dimethylhex-4-enyl]-3-methylcyclohex-2-en-1-one
• CAS No.: 72441-70-4
• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 220.355
• Mol file: 72441-70-4.mol

Synonyms:(6R)-[(1R)-1,5-dimethylhex-4-enyl]-3-methylcyclohex-2-en-1-one

Chemical Property of (6R)-[(1R)-1,5-dimethylhex-4-enyl]-3-methylcyclohex-2-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R)-[(1R)-1,5-dimethylhex-4-enyl]-3-methylcyclohex-2-en-1-one

There total 8 articles about (6R)-[(1R)-1,5-dimethylhex-4-enyl]-3-methylcyclohex-2-en-1-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: 45.0%

(1RS,4RS,1′R)-4-(1′,5′-dimethylhex-4′-enyl)-1-methylcyclohex-2-en-1-ol (446018-20-8) → (6R)-[(1R)-1,5-dimethylhex-4-enyl]-3-methylcyclohex-2-en-1-one (72441-70-4) + (6S)-[(1R)-1,5-dimethylhex-4-enyl]-3-methylcyclohex-2-en-1-one

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 2.5h;

DOI:10.1039/b200629b

Reference yield:

(6R,7R)-zingiberenol → (6R)-[(1R)-1,5-dimethylhex-4-enyl]-3-methylcyclohex-2-en-1-one (72441-70-4) + (6S)-[(1R)-1,5-dimethylhex-4-enyl]-3-methylcyclohex-2-en-1-one

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dichloromethane; at 0 - 25 ℃; for 2h; Overall yield = 37 percent; Overall yield = 119 mg; Inert atmosphere;

DOI:10.1021/acs.jnatprod.0c00517

Reference yield:

(R)-Citronellal (2385-77-5) → (6R)-[(1R)-1,5-dimethylhex-4-enyl]-3-methylcyclohex-2-en-1-one (72441-70-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / diethylamino(trimethyl)silane / acetonitrile / 48 h / Heating

2: 89 percent / aq. KOH; tetrabutylammonium hydroxide / tetrahydrofuran; diethyl ether / 4 h / Heating

3: 96 percent / diethyl ether / 2.5 h / -78 °C

4: 45 percent / PCC / CH₂Cl₂ / 2.5 h / 20 °C

With potassium hydroxide; tetra(n-butyl)ammonium hydroxide; N,N-diethyl-1,1,1-trimethylsilanamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1039/b200629b

upstream raw materials:

(1RS,4RS,1′R)-4-(1′,5′-dimethylhex-4′-enyl)-1-methylcyclohex-2-en-1-ol

(R)-Citronellal

4-[(1R)-1,5-dimethylhex-4-enyl]cyclohex-2-en-1-one

(2RS,3R)-3,7-Dimethyl-2-(3-oxobutyl)oct-6-enal

Downstream raw materials:

2-((R)-4-Bromo-1,5-dimethyl-hex-4-enyl)-5-methyl-phenol

4-Bromo-2-((R)-4-bromo-1,5-dimethyl-hex-4-enyl)-5-methyl-phenol

2-[(1R)-1,5-dimethylhex-4-enyl]-4-bromo-5-methylphenol