(2R,6R)-2,6-Dimethyl-2-((E)-4-methyl-penta-1,3-dienyl)-cyclohexanone

Base Information

• Chemical Name: (2R,6R)-2,6-Dimethyl-2-((E)-4-methyl-penta-1,3-dienyl)-cyclohexanone
• CAS No.: 179915-20-9
• Molecular Formula: C₁₄H₂₂O
• Molecular Weight: 206.328
• Mol file: 179915-20-9.mol

Synonyms:(2R,6R)-2,6-Dimethyl-2-((E)-4-methyl-penta-1,3-dienyl)-cyclohexanone

Chemical Property of (2R,6R)-2,6-Dimethyl-2-((E)-4-methyl-penta-1,3-dienyl)-cyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6R)-2,6-Dimethyl-2-((E)-4-methyl-penta-1,3-dienyl)-cyclohexanone

There total 11 articles about (2R,6R)-2,6-Dimethyl-2-((E)-4-methyl-penta-1,3-dienyl)-cyclohexanone 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:

(E)-3-((R)-1-Methyl-2-oxo-cyclohexyl)-acrylic acid methyl ester (179915-19-6) → (2R,6R)-2,6-Dimethyl-2-((E)-4-methyl-penta-1,3-dienyl)-cyclohexanone (179915-20-9)

Guidance literature:

Multi-step reaction with 6 steps

1: TsOH / benzene / Heating

2: LiAlH₄ / diethyl ether / 3 h

3: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, 0 deg C, 10 min

4: 1.) nBuLi / 1.) ether, room temperature, 1 h, 2.) ether, 50 min

5: TsOH / acetone; H₂O / 50 °C

6: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 1 h, 2.) THF, 9 h

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In diethyl ether; water; acetone; benzene;

DOI:10.1021/jo952253u

Reference yield:

(R)-(+)-2-(2'-carbomethoxyethyl)-2-methylcyclohexanone (53068-89-6,112898-44-9,150927-14-3,94089-47-1) → (2R,6R)-2,6-Dimethyl-2-((E)-4-methyl-penta-1,3-dienyl)-cyclohexanone (179915-20-9)

Guidance literature:

Multi-step reaction with 7 steps

1: TsOH

2: 1.) lithium diisopropylamide, PhSeBr, 2.) H₂O₂

3: LiAlH₄ / diethyl ether / 3 h

4: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, 0 deg C, 10 min

5: 1.) nBuLi / 1.) ether, room temperature, 1 h, 2.) ether, 50 min

6: TsOH / acetone; H₂O / 50 °C

7: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 1 h, 2.) THF, 9 h

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; Phenylselenyl bromide; dihydrogen peroxide; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In diethyl ether; water; acetone;

DOI:10.1021/jo952253u

Reference yield:

[2-Methyl-cyclohex-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine (193468-09-6) → (2R,6R)-2,6-Dimethyl-2-((E)-4-methyl-penta-1,3-dienyl)-cyclohexanone (179915-20-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 120 h / Ambient temperature

2: AcOH / H₂O

3: TsOH

4: 1.) lithium diisopropylamide, PhSeBr, 2.) H₂O₂

5: LiAlH₄ / diethyl ether / 3 h

6: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, 0 deg C, 10 min

7: 1.) nBuLi / 1.) ether, room temperature, 1 h, 2.) ether, 50 min

8: TsOH / acetone; H₂O / 50 °C

9: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 1 h, 2.) THF, 9 h

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; Phenylselenyl bromide; dihydrogen peroxide; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In diethyl ether; water; acetone;

DOI:10.1021/jo952253u

upstream raw materials:

(R)-2-Methyl-2-((E)-4-methyl-penta-1,3-dienyl)-cyclohexanone

methyl iodide

(R)-(+)-2-(2'-carbomethoxyethyl)-2-methylcyclohexanone

[2-Methyl-cyclohex-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine

Downstream raw materials:

2-[(R)-2,6-Dimethyl-6-((E)-4-methyl-penta-1,3-dienyl)-cyclohex-1-enylmethyl]-benzene-1,4-diol

2-[(R)-2,6-Dimethyl-6-((E)-4-methyl-penta-1,3-dienyl)-cyclohex-1-enylmethyl]-4-methoxy-1-methoxymethoxy-benzene

2-[(R)-2,6-Dimethyl-6-((E)-4-methyl-penta-1,3-dienyl)-cyclohex-1-enylmethyl]-1,4-bis-methoxymethoxy-benzene

2-[(1S,2R,6R)-1-Hydroxy-2,6-dimethyl-2-((E)-4-methyl-penta-1,3-dienyl)-cyclohexylmethyl]-benzene-1,4-diol