cis,trans-methyl 2-oxo-5,5,8a-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalenecarboxylate

Base Information

• Chemical Name: cis,trans-methyl 2-oxo-5,5,8a-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalenecarboxylate
• CAS No.: 95999-06-7
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.338
• Mol file: 95999-06-7.mol

Synonyms:

Chemical Property of cis,trans-methyl 2-oxo-5,5,8a-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalenecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis,trans-methyl 2-oxo-5,5,8a-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalenecarboxylate

There total 1 articles about cis,trans-methyl 2-oxo-5,5,8a-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalenecarboxylate 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:

trans-methyl 3-oxo-5-(2,6,6-trimethylcyclohexen-1-yl)pent-4-enoate (68380-14-3) → methyl 3-oxo-5-(2-methylene-6,6-dimethylcyclohex-1-ylidene)pentanoate (68380-15-4) + cis,trans-methyl 2-oxo-5,5,8a-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalenecarboxylate (95999-06-7) + methyl 2-(5,5,8a-trimethyl-5,6,7,8-tetrahydro-1(8aH)-benzopyranyl)acetate (68380-16-5) + cis-methyl 2-oxo-5,5,8a-trimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalenecarboxylate (95999-05-6)

Guidance literature:

With sodium methylate; In methanol; Mechanism; Product distribution; Irradiation; other reagents, other solvents,other reaction times;

DOI:10.1021/jo00211a030

Reference yield:

cis,trans-methyl 2-oxo-5,5,8a-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalenecarboxylate (95999-06-7) → (Z)-3-(3-((tert-butyldimethylsilyl)oxy)-4-methylphenyl)-1-(2,5,5,8a-tetramethyl-2,4-bis((trimethylsilyl)oxy)decahydronaphthalen-1-yl)but-2-en-1-ol

Guidance literature:

Multi-step reaction with 8 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 °C / Inert atmosphere

2.1: manganese(IV) oxide / dichloromethane / 24 h / 23 °C / Inert atmosphere

3.1: diethyl ether / -78 - 23 °C / Inert atmosphere

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 25 h / 23 °C / Inert atmosphere

5.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 24 h / Reflux; Inert atmosphere

6.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 5 h / 23 °C / Inert atmosphere

7.1: triethylamine / dichloromethane / 0.5 h / -15 °C / Inert atmosphere

8.1: tert.-butyl lithium / tetrahydrofuran / 0.45 h / -78 °C / Inert atmosphere

8.2: 0.5 h / -78 °C / Inert atmosphere

With manganese(IV) oxide; lithium aluminium tetrahydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tert.-butyl lithium; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1039/c9ob00745h

Reference yield:

cis,trans-methyl 2-oxo-5,5,8a-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalenecarboxylate (95999-06-7) → C37H66O3Si3

Guidance literature:

Multi-step reaction with 9 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 °C / Inert atmosphere

2.1: manganese(IV) oxide / dichloromethane / 24 h / 23 °C / Inert atmosphere

3.1: diethyl ether / -78 - 23 °C / Inert atmosphere

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 25 h / 23 °C / Inert atmosphere

5.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 24 h / Reflux; Inert atmosphere

6.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 5 h / 23 °C / Inert atmosphere

7.1: triethylamine / dichloromethane / 0.5 h / -15 °C / Inert atmosphere

8.1: tert.-butyl lithium / tetrahydrofuran / 0.45 h / -78 °C / Inert atmosphere

8.2: 0.5 h / -78 °C / Inert atmosphere

9.1: 72 h / 23 °C / Inert atmosphere

With manganese(IV) oxide; lithium aluminium tetrahydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tert.-butyl lithium; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1039/c9ob00745h

upstream raw materials:

trans-methyl 3-oxo-5-(2,6,6-trimethylcyclohexen-1-yl)pent-4-enoate

Downstream raw materials:

jolkinolide E

jolkinolide E