3-[(1R,6R)-1,3-dimethyl-6-(1-methylethenyl)-2-oxo-3-cyclohexenyl]-1-propanal

Base Information

• Chemical Name: 3-[(1R,6R)-1,3-dimethyl-6-(1-methylethenyl)-2-oxo-3-cyclohexenyl]-1-propanal
• CAS No.: 183072-24-4
• Molecular Formula: C₁₄H₂₀O₂
• Molecular Weight: 220.312
• Mol file: 183072-24-4.mol

Synonyms:3-[(1R,6R)-1,3-dimethyl-6-(1-methylethenyl)-2-oxo-3-cyclohexenyl]-1-propanal

Chemical Property of 3-[(1R,6R)-1,3-dimethyl-6-(1-methylethenyl)-2-oxo-3-cyclohexenyl]-1-propanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(1R,6R)-1,3-dimethyl-6-(1-methylethenyl)-2-oxo-3-cyclohexenyl]-1-propanal

There total 4 articles about 3-[(1R,6R)-1,3-dimethyl-6-(1-methylethenyl)-2-oxo-3-cyclohexenyl]-1-propanal 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: 94.0%

(5R,6R)-6-(3,3-diethoxypropyl)-2,6-dimethyl-5-(1-methylethenyl)-2-cyclohexen-1-one (212185-22-3) → 3-[(1R,6R)-1,3-dimethyl-6-(1-methylethenyl)-2-oxo-3-cyclohexenyl]-1-propanal (183072-24-4)

Guidance literature:

With pyridinium p-toluenesulfonate; In water; acetone; Heating;

DOI:10.1016/S0040-4020(99)00725-5

Reference yield:

(S)-p-mentha-6,8-dien-2-one (2244-16-8,6485-40-1) → 3-[(1R,6R)-1,3-dimethyl-6-(1-methylethenyl)-2-oxo-3-cyclohexenyl]-1-propanal (183072-24-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / LDA

2: 1.) LDA / 1.) THF, -78 deg C, 1 h, then room temp., 1 h, 2.) THF, -78 deg C to room temp., 3 h

3: 92 percent / pyridinium p-toluenesulfonate / acetone; H₂O / 1 h / Heating

With pyridinium p-toluenesulfonate; lithium diisopropyl amide; In water; acetone;

DOI:10.1021/jo980311g

Reference yield:

6-methyl-carvone (158930-44-0) → 3-[(1R,6R)-1,3-dimethyl-6-(1-methylethenyl)-2-oxo-3-cyclohexenyl]-1-propanal (183072-24-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA / 1.) THF, -78 deg C, 1 h, then room temp., 1 h, 2.) THF, -78 deg C to room temp., 3 h

2: 92 percent / pyridinium p-toluenesulfonate / acetone; H₂O / 1 h / Heating

With pyridinium p-toluenesulfonate; lithium diisopropyl amide; In water; acetone;

DOI:10.1021/jo980311g

upstream raw materials:

(5R,6R)-6-(3,3-diethoxypropyl)-2,6-dimethyl-5-(1-methylethenyl)-2-cyclohexen-1-one

(S)-p-mentha-6,8-dien-2-one

6-methyl-carvone

Downstream raw materials:

(5R,6R)-2,6-dimethyl-5-(1-methylethenyl)-6-((E)-4-methyl-5-oxo-3-hexenyl)-2-cyclohexen-1-one

(1aS,1bR,3aR,4R,5S,7aR,7bR,9aR)-4-(2,5-Bis-methoxymethoxy-3-methyl-benzyl)-9a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-ol

(1aS,1bR,3aR,4S,5S,7aR,7bR,9aR)-4-(2,5-Bis-methoxymethoxy-3-methyl-benzyl)-9a-(tert-butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-ol

stypodiol