(2S,5S)-2-Methyl-5-((S)-1-methyl-but-3-enyl)-cyclohexanone

Base Information

• Chemical Name: (2S,5S)-2-Methyl-5-((S)-1-methyl-but-3-enyl)-cyclohexanone
• CAS No.: 113161-41-4
• Molecular Formula: C₁₂H₂₀O
• Molecular Weight: 180.29
• Mol file: 113161-41-4.mol

Synonyms:

Chemical Property of (2S,5S)-2-Methyl-5-((S)-1-methyl-but-3-enyl)-cyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S)-2-Methyl-5-((S)-1-methyl-but-3-enyl)-cyclohexanone

There total 14 articles about (2S,5S)-2-Methyl-5-((S)-1-methyl-but-3-enyl)-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:

(1S,2S,5S)-2-Methyl-5-((S)-1-methyl-but-3-enyl)-cyclohexanol → (2S,5S)-2-Methyl-5-((S)-1-methyl-but-3-enyl)-cyclohexanone (113161-41-4)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; Yield given;

DOI:10.1021/jo00242a053

Reference yield:

(1S,2S,5S)-5-(1-hydroxypropan-2-yl)-2-methylcyclohexanol → (2S,5S)-2-Methyl-5-((S)-1-methyl-but-3-enyl)-cyclohexanone (113161-41-4)

Guidance literature:

Multi-step reaction with 14 steps

1: pyridine

2: pyridinium p-toluenesulfonate (PPTS) / CH₂Cl₂

3: aq. KOH

4: pyridinium chlorochromate (PCC) , NaOAc / CH₂Cl₂

5: NaClO₂, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O

6: aq. acetic acid / 80 °C

7: 67 percent / p-toluenesulfonic acid / toluene / Heating

8: lithium diisopropylamide (LDA) / hexamethylphosphoric acid triamide

9: H₂O₂

10: 79 percent / CuI, dimethyl sulfide, trimethylsilyl chloride / tetrahydrofuran / -40 °C

11: 84 percent / LiAlH₄ / tetrahydrofuran / 1 h / 25 °C

12: Et₃N, 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂

13: lithium triethylborohydride / tetrahydrofuran

14: pyridinium chlorochromate (PCC) / CH₂Cl₂

With pyridine; dmap; potassium hydroxide; sodium chlorite; copper(l) iodide; lithium aluminium tetrahydride; chloro-trimethyl-silane; 2-methyl-but-2-ene; dimethylsulfide; dihydrogen peroxide; sodium acetate; pyridinium p-toluenesulfonate; lithium triethylborohydride; toluene-4-sulfonic acid; acetic acid; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; toluene; tert-butyl alcohol;

DOI:10.1021/jo00242a053

Reference yield:

(1S,5S,8S)-4,8-Dimethyl-2-oxa-bicyclo[3.3.1]nonan-3-one → (2S,5S)-2-Methyl-5-((S)-1-methyl-but-3-enyl)-cyclohexanone (113161-41-4)

Guidance literature:

Multi-step reaction with 7 steps

1: lithium diisopropylamide (LDA) / hexamethylphosphoric acid triamide

2: H₂O₂

3: 79 percent / CuI, dimethyl sulfide, trimethylsilyl chloride / tetrahydrofuran / -40 °C

4: 84 percent / LiAlH₄ / tetrahydrofuran / 1 h / 25 °C

5: Et₃N, 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂

6: lithium triethylborohydride / tetrahydrofuran

7: pyridinium chlorochromate (PCC) / CH₂Cl₂

With dmap; copper(l) iodide; lithium aluminium tetrahydride; chloro-trimethyl-silane; dimethylsulfide; dihydrogen peroxide; lithium triethylborohydride; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1021/jo00242a053

upstream raw materials:

(1S,5S,8S)-8-Methyl-4-methylene-2-oxa-bicyclo[3.3.1]nonan-3-one

(1S,2S,5S)-5-((S)-1-Hydroxymethyl-but-3-enyl)-2-methyl-cyclohexanol

(1S,4S,5S,8S)-4-Allyl-8-methyl-2-oxa-bicyclo[3.3.1]nonan-3-one

Downstream raw materials:

(4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol

Formic acid (4S,6S,6aR,9S)-2-benzyloxy-4-formyl-3,6,9-trimethyl-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl ester

(2S,3R,4S,5R)-2-[(4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yloxy]-tetrahydro-pyran-3,4,5-triol

Formic acid (4S,6S,6aR,9S)-2-benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-3,6,9-trimethyl-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl ester