Methyl 2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>acetate

Base Information

• Chemical Name: Methyl 2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>acetate
• CAS No.: 229010-37-1
• Molecular Formula: C₁₅H₂₄O₂
• Molecular Weight: 236.354
• Mol file: 229010-37-1.mol

Synonyms:Methyl 2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>acetate

Chemical Property of Methyl 2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>acetate

There total 12 articles about Methyl 2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>acetate 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:

(4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene (149404-74-0) → Methyl 2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>acetate (229010-37-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / K₂CO₃ / methanol

2: LDA, HMPA / tetrahydrofuran; hexane / 1.) -78 deg C, 30 min, 2.) -78 to -40 deg C, 4 h

3: 81 percent / LiAlH₄ / tetrahydrofuran / 2 h / -50 °C

4: 87 percent / imidazole / dimethylformamide / 1 h

5: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, hexane, 50 min

6: AIBN, HSnBu₃ / toluene / 0.5 h / 90 °C

7: Bu₄NF / tetrahydrofuran / 6 h

8: CrO₃, H₂SO₄, H₂O / acetone

9: diethyl ether / 0 °C

With 1H-imidazole; chromium(VI) oxide; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); sulfuric acid; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1039/a809983i

Reference yield:

(3R,4R)-3-Methyl-4-isopropenyl-3-vinylcyclohexanone (149404-72-8) → Methyl 2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>acetate (229010-37-1)

Guidance literature:

Multi-step reaction with 8 steps

1: LDA, HMPA / tetrahydrofuran; hexane / 1.) -78 deg C, 30 min, 2.) -78 to -40 deg C, 4 h

2: 81 percent / LiAlH₄ / tetrahydrofuran / 2 h / -50 °C

3: 87 percent / imidazole / dimethylformamide / 1 h

4: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, hexane, 50 min

5: AIBN, HSnBu₃ / toluene / 0.5 h / 90 °C

6: Bu₄NF / tetrahydrofuran / 6 h

7: CrO₃, H₂SO₄, H₂O / acetone

8: diethyl ether / 0 °C

With 1H-imidazole; chromium(VI) oxide; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); sulfuric acid; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1039/a809983i

Reference yield:

(1R,4R,5R)-5-Isopropenyl-4-methyl-2-oxo-4-vinyl-cyclohexanecarboxylic acid ethyl ester (202194-28-3) → Methyl 2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>acetate (229010-37-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 95 percent / NaH, HMPA / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) 0 deg c to r.t., 4 h

2: NaOH, H₂O / dimethylsulfoxide / 12 h / 50 °C

3: diethyl ether / 0 °C

4: 81 percent / LiAlH₄ / tetrahydrofuran / 2 h / -50 °C

5: 87 percent / imidazole / dimethylformamide / 1 h

6: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, hexane, 50 min

7: AIBN, HSnBu₃ / toluene / 0.5 h / 90 °C

8: Bu₄NF / tetrahydrofuran / 6 h

9: CrO₃, H₂SO₄, H₂O / acetone

10: diethyl ether / 0 °C

With 1H-imidazole; chromium(VI) oxide; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); sulfuric acid; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; sodium hydride; In tetrahydrofuran; diethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1039/a809983i

upstream raw materials:

diazomethane

(4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene

(1R,4R,5R)-5-Isopropenyl-4-methyl-2-oxo-4-vinyl-cyclohexanecarboxylic acid ethyl ester

(3R,4R)-3-Methyl-4-isopropenyl-3-vinylcyclohexanone

Downstream raw materials:

Methyl 2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>-4-<(5R)-2,2,4,4-tetramethyl-1,3-dioxolan-5-yl>butanoate

Methyl (5R)-2-<(1S,3R,4R)-3-isopropenyl-4-methyl-4-vinylcyclohexyl>-5,6-dihydroxy-6-methylheptanoate

lobatrienolide

lobatrientriol